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Find Caribbean Crewed Yachts for the Vacation of a Lifetime

The Caribbean is one of the most popular destinations for yacht charters in the world, featuring crystal-blue waters, white-sand beaches, and more than 5,000 islands and cays to explore. With so many islands to choose from, your Caribbean yacht charter itinerary can be tailored to your preferences, giving you the perfect opportunity to island-hop and explore everything the tropical islands have to offer while comfortably kicking back inside luxurious accommodations on the water.

On your private yacht charter , you will be able to explore lively harbors, secluded beaches, tropical rainforests, world-class dive sites, and much more. The possibilities are endless!

Caribbean Yacht Charter Highlights

• More than 5,000 islands and cays to explore
• A great winter destination
• Crystal-clear, sparkling blue waters
• Long stretches of white-sand beaches
• Luxury hotels, five-star restaurants, and spas
• Islands with their own unique cultures and cuisines
• A large selection of crewed yachts for charter

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282.2ft / 84m

239.6ft / 71m

228.6ft / 68m

223.7ft / 67m

Caribbean Yachting Season

The Caribbean high season for yacht charters runs from mid-December to early May, with Christmas and New Year’s the most popular and busiest times of the year. But due to the islands’ locations near the equator, temperatures remain ideal throughout the year, making off-season charters just as enjoyable.

Keep in mind, however, that there is an increased chance for storms and hurricanes during the summer season, mainly from mid-August to mid-November. Most charter yachts leave the area during that time.

Caribbean Crewed Motor Yacht Charters

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162ft / 48m

Sweet Escape

130ft / 39m

116ft / 34m

Caribbean Catamaran Charters

105ft / 31m

Serenity Now

Caribbean Crewed Sailing Yacht Charters

Area Guide: Caribbean Charter Destinations

Are you ready to explore all that the Caribbean has to offer? There are three main island areas in the Caribbean, all fantastic destinations for Caribbean charter yacht vacations.

The Grenadines

The Grenadines are untouched by mass tourism and industry, and they are the perfect charter destination if you are looking for solitude and you enjoy exploring remote areas. A great combination of lush rain forests and sandy beaches awaits!

This is a great summer charter destination because the islands aren’t usually affected by hurricanes.

The Leeward Islands

Leeward Islands yacht rentals offer the perfect combination of luxury and solitude. You can visit the glitzy islands of St. Maarten and St. Barts one day and get lost in the remoteness and tranquility of Anguilla the next day.

These islands are rich in history and offer great restaurants, upscale resorts, and trendy harbors.

The Virgin Islands

The Virgin Islands are the perfect location for first-time charterers and families because of their calm waters, protected natural anchorages, and short distances between the islands.

The BVI are a great destination for a catamaran or sailing yacht charter. Caribbean locations here have constant yet mild trade winds year round, and the area offers fantastic diving and snorkeling.

Where Can I Charter a Yacht?

When you choose Worldwide Boat as your Caribbean yacht charter broker, we can help you charter a luxury boat anywhere in the Caribbean or anywhere else you’d like to go, from the Mediterranean to Alaska to the Galapagos Islands.

How Do I Book a Private Yacht?

The best Caribbean yacht charters can be booked in just a few easy steps:

• Choose our experienced yacht charter specialists to assist you through the process of booking a yacht.
• Search by destination or by boat, or use our advanced search tool to filter your options by the number of guests, yacht type, destination, and/or your budget.
• Pick the option that best fits your needs and your dream vacation.
• Reserve your yacht by signing a contract with the yacht owner.
• Enjoy your vacation!

How Much Does it Cost to Charter a Yacht in the Caribbean?

Weekly rates for Caribbean boat charters are dependent on a number of factors, including the type of yacht, the season, and your destination. Motor yachts, for example, typically range from $15,000 (yachts up to 80 feet) to $150,000 or more (yachts over 150 feet) per week.

During the Caribbean high season (Christmas, New Year’s, and January/February), yacht charter Caribbean prices tend to increase slightly. Areas with large charter fleets, like St. Martin, tend to have more competitive pricing than areas with smaller fleets.

How Much Does it Cost to Charter a Catamaran in the Caribbean?

Most catamarans offer all-inclusive rates, which start at $10,000 for catamarans under 50 feet and run up to $50,000 or more for catamarans of 80 feet or more. The Caribbean is an ideal destination for a catamaran charter, and across the region, you’ll find a variety of sailing and power cats available for charter.

Ultimately, the cost of a catamaran charter is dependent on the time you visit, where you go, local taxes, and the number of ports you visit. A luxury yacht charter in the Caribbean’s high season (New Year’s or Christmas) will cost significantly more than a catamaran charter in summer.

Can I Rent a Yacht for a Day?

Rates for yacht rentals are usually weekly, but when you talk to a Caribbean yacht charter broker at Worldwide Boat, we can look at your budget, plans, and interests to help you get the best experience possible.

Caribbean Yachting Hotspots

Caribbean sailing charters give you access to white-sand beaches and laid-back island vibes, but they can also offer action-packed itineraries. From island-hopping and hiking to snorkeling and cliff-jumping, adventure awaits on a Caribbean yacht charter!

Some of the region’s must-see destinations include:

• St. Martin : Known for its upscale eateries and amazing cuisine, as well as high-end spas, shopping and casinos, St. Martin is the yachting capital of the Caribbean. This island is part French and part Dutch, and it’s close to islands like St. Barts and Anguilla, making it a favorite jumping-off point for island-hopping adventures.
• St. Barts : St. Barts (sometimes called St. Barths) beckons A-listers to its posh beach clubs, fashionable shops, and five-star eateries. Visitors will find a collection of truly spectacular powdery beaches, Michelin-starred restaurants, and excellent shoreside amenities, all within cruising distance of St. Martin.
• Antigua : Antigua epitomizes the relaxation and bliss of the Caribbean. Known for its 365 beaches (one for every day of the year), the tiny island is a sailor’s dream, offering warm waters, steady winds, safe anchorages, and a lively regatta calendar.
• Grenada : Grenada is revered for its beautiful beaches, abundant marine wildlife, and vibrant cuisine (spiced with local nutmeg, mace, and allspice). Spend a day relaxing on Grand Anse Beach, which is consistently ranked one of the best in the world. Island-hop to neighboring isles like Petite Martinique, or spend a day snorkeling one of Grenada’s famous reefs.
• Anguilla : Anguilla is one of the most tranquil Leeward islands. Escape to Dream Bay or one of the numerous nearby coral cays for some supreme R&R. A diving and snorkeling mecca, Anguilla is home to some of the Caribbean’s best shipwreck dives. Plus, the island boasts a calendar of must-see festivals and events, including a jazz festival in November and Carnival in August.

Why Charter a Yacht in the Caribbean?

The best Caribbean yacht charters offer a bit of everything: Relaxation, sun-soaked beaches, delicious culinary treats, refreshing rum-infused cocktails, and calm waters for cruising. Here are some highlights:

The Inescapable Beauty of White-Sand Beaches

Caribbean beaches have almost a mythical quality to them. It’s no wonder explorers were once willing to board wooden ships and travel thousands of miles just to see them in person.

Every island offers a selection of untouched and charming beaches for you to explore. From one-of-a-kind places like “Pig Beach” in the Bahamas to the cosmopolitan Great Bay Beach in Philipsburg, St. Martin, the beaches across the Caribbean offer legendary sights and attractions.

Colorful Celebrations and Friendly Faces

The Caribbean is known for its parades, bars, nightclubs, and parties, not to mention world-famous cocktails. When you want to step off of your luxury yacht charter, Caribbean shores and islands offer a world of fun to immerse yourself in.

A few must-see events include the St. Barth’s Bucket (if you’re into superyacht racing), the annual Carnival celebration, and the St. Lucia Jazz & Arts Festival .

Amazing Wildlife and Adventure

If snorkeling in vibrant and colorful coral reefs, diving into underwater museums, or parasailing over clear waters are some of the items on your bucket list, you can certainly get it all done during your visit to the Caribbean.

You’ll find a variety of unique adventures, from the underwater sculpture park of the Grenadines to the natural seaside baths in Virgin Gorda and hiking the Pitons in St. Lucia. The Caribbean gives you to plenty of chances to get outside and enjoy yourself.

Nonstop Relaxation

Because the area is so close to the equator, the Caribbean offers warm weather to lounge in all year round. Feel pampered aboard a luxury crewed rental yacht, and then feel calm while sinking your toes into soft, powdery white sand. Enjoy the spas, rum cocktails, and quiet, isolated beaches: Charter guests can experience supreme relaxation in the Caribbean.

Book Your Caribbean Charter With Worldwide Boat

Discover the beauty of the Caribbean with a luxury crewed yacht charter. Contact a broker with Worldwide Boat today to learn more about available yachts and itineraries for the Caribbean.

Last edited by Katja Kukovic

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• Caribbean Yacht Charter

Perhaps the best tropical yacht charter spot worldwide, there are over 700 islands to choose from in the Caribbean. However, Caribbean yacht charters can be split into two main area: the Greater Antilles and the Lesser Antilles. The Greater Antilles is home to countries like the Dominican Republic, Jamaica and Cuba while the Lesser Antilles can be subdivided into the Windward and Leeward Islands. The Leeward islands include St Kitts and Nevis, the British Virgin Islands, Anguilla along with Antigua and Barbuda. The Windward Islands comprise the Grenadines, Grenada, Barbados, Dominica, St Vincent and St Lucia.

ALFA NERO | From EUR€ 812,000/wk

Maltese falcon | from eur€ 480,000/wk, seven sins | from eur€ 270,000/wk, g2 | from us$ 85,000/wk.

Sailing Yachts Under 100' - Sailing Yachts Over 100' - Motor Yachts Under 100' - Motor Yachts Over 100' - Catamarans Over 50'

The stunning and diverse Caribbean beckons travelers back year after year. With its beautiful climate, fantastic coral reefs, palm trees and exotic tropical islands, there are lots of reasons to make this your next sailing destination. Don’t forget the rum cocktails either! As the second largest yachting area, only after the Mediterranean, there are many luxury yachts available for your Caribbean yacht charter and you can view some of the yachts below or here .

Reviews of Caribbean Charter Vacations | Caribbean Holiday Fact File | Top Caribbean Spots | Sample Itinerary | Charter Yachts Available

The Bahamas and Turks and Caicos are not really in the Caribbean although are known as superyacht destinations in the Caribbean. Wherever you decide to charter a luxury superyacht in the Caribbean you will enjoy a totally relaxing vacation and beautiful scenery.

How Much Does it Cost To Charter in The Caribbean?

Caribbean yacht charter prices vary according to the size, style and age of the yacht you rent. Our luxury superyacht charters rent from 30,000 USD to over 1,000,000 per week, plus expenses, in the form of an advanced provisioning allowance (APA). Conversely, smaller 'all inclusive' type vacations cost between USD 15,000 to 50,000 per week. View the list of yachts and prices here .

Experience the luxury of Crewed Private Yachts in the Caribbean

A traditional hot spot for crewed charters, the Caribbean is considered “the king of yachting vacations”, so please contact us here to go on your private charter. Whether you agree with this or not, you like most people will have heard of the Caribbean as a great yacht charter destination. This is because this location covers a huge area and offer fantastic diversity. It is beautiful and warm, has amazing beaches, interesting cultures and perhaps most importantly, the Caribbean has a huge selection of crewed yachts, luxury yachts and superyachts which you can rent and experience a truly magnificent vacation around the various Island groups. The Caribbean is a natural wonderland onshore, but probably most importantly, it has an ocean laden with treasures, from tiny beach ridden coral atolls to substantial mountainous islands exuding rich and colorful cultures. An area which is famous for its beautiful waterways and islands, there is no better way to experience the Caribbean than on a crewed luxury yacht vacation.

Some of the Recommended Caribbean Yacht Spots:

Popular places to visit on a yacht include Antigua , St Barts , Anguilla , St Martin , The British Virgin Islands , The US Virgin Islands , the Grenadines and many more – see more below.

More than ever crewed luxury yachts are beginning to explore more exotic and remote Caribbean Islands, so ask your charter broker or captain for more information on some of these more remote treasures. Due to the scale and diversity of the different areas of the Caribbean we have covered the major charter locations individually. Please note that if there is a charter boat cruising area, not covered here that you are interested in, please contact us and we will provide you with that information personally in the form of a yacht charter itinerary.

As one of the most popular locations in the world, second only to the Mediterranean in popularity, the types of boats available for rental in the Caribbean include all the main types such as motor, sailing, skippered, crewed yachts, catamarans, power boats, sailboat, luxury yachts as well as the ever growing superyacht and mega yachts. Both beginner and experts alike are drawn to the Caribbean for its warm winds, protected waterways and beautiful anchorages. The Caribbean is a special place that has beautiful tropical islands that lie snug within a tropical island necklace as laid out on a large blue sea.

The Caribbean is also steeped in a fertile history of sailing adventure. Ever since the days of galleons and pirates the Caribbean has been host to some of the most satisfying sailing anywhere in the world. On your Caribbean yachting vacation you can find, an incredible amount of choice and variety and all in a relatively small area - thriving bars and Caribbean nightlife; first rate cuisine; spectacular white powder beaches; lush tropical rain forest; cloud-fringed mountain peaks; exotic bird life; amazing diving and snorkeling and a serene blend of European sophistication and warm Caribbean hospitality. The problem is, with so many superb Caribbean yachting locations and charter boats to choose form, where do you start when planning a holiday? With CharterWorld of course…

The Time of Year to Charter a Yacht in the Caribbean:

The main Caribbean sailing season runs from November through to July. The Caribbean primary high season is from mid-December to March, when the winter escapees from North America and Europe arrive in their greatest numbers. The hurricane season is from late July to early October, although hurricanes are in general rare in the southern Caribbean. Unfortunately, they can be prevalent around Cuba, Bahamas and the east coast of the U.S. every few years. This is the least expensive time for chartering in the Caribbean and there are some really good deals are available. However, as well as running the risk of storms, this time of year also tends to be associated with lighter (or non-existent) winds.

As with many boating locations the Caribbean shoulder season, in this case from April to July, is also a great time to charter a boat as there are less shore based visitors, some lovely settled sunny weather, and warm yet steady breeze. The Caribbean is made up of many different multi-nation (and multi-cultural) volcanic islands. There are amazing sailing grounds stretching from Cuba and Jamaica in the west, through the Dominican Republic, Puerto Rico, The Virgin Islands, The Leeward Islands and the Windward Islands, finishing with Trinidad and Tobago off the coast of Venezuela.

Caribbean Yachting Hot Spots:

Here is a brief list of some of the Caribbean hot spots to consider experiencing when you rent a luxury crewed charter yacht. This is by no means an extensive list and there is more information on things to see and do in the Caribbean under each Caribbean private yacht location. Also, when you hire a yacht with us we will supply you with a customised hand written itinerary suggestion so that you and your crew have a few ideas to choose from on your charter.

General Places/Events Worthy of Experiencing:

- Gustavia Harbour in St Barts - shopping, nightlife, restaurants and European quintessence - Nelson in Dockyards in Antigua - history and beauty in a harbour - Sunset in St Lucia - St Kitts for the beauty, history and magnificent views from Brimstone Hill Fortress - Anegada for its deserted beaches, fringed reefs and the unique flora and fauna of the salt ponds, home to the pink flamingo - The BVIs for the beautiful beaches and anchorages - Guadeloupe for its diversity - one side offers cosmopolitan flair, bordered by beaches and coral reefs and the other has open lands with the fertile, volcanic peaks , rain forest and waterfalls.

How to get to the Caribbean

There are direct flights from the UK and the US to Barbados, Jamaica, St Lucia and Antigua. Some Caribbean islands require a connecting flight as they have small airports which cannot handle large aeroplanes. Across the Caribbean, many islands have private jet facilities with fantastic runways.

What is the currency in the Caribbean?

Various currencies are used in the Caribbean. For instance, in Anguilla, Dominica, Grenada, St Kitts and Nevis, St Lucia, St Vincent, the Grenadines and Antigua, the East Caribbean dollar is the currency. Jamaica, Barbados, the Cayman Islands and the Bahamas have their very own currency. US dollars are accepted on most of the islands however the ATMs tend to have only the local currency.

Language spoken

There are four main languages spoken in the Caribbean, French, Spanish, Dutch and English. English is the first or second language and is mostly used when tourists visit. The official language of Haiti is Haitian Creole while Papiamento is used in Curacao, Bonaire and Aruba. Different creoles and local patois are also spoken on the various islands.

Time Zone in the Caribbean

Two time zones are used in the Caribbean. GMT -5 and GMT -4. Daylight saving time is implemented in many countries including Bermuda, Cuba, Haiti, the Bahamas including the Turks and Caicos Islands.

Visas and customs immigration

British and American tourists do not need visas if they are staying in the Caribbean for less than 90 days. It’s advisable to check the exact requirements for the countries you intend visiting. American tourists are still not allowed to visit Cuba although this may change in the future.

What to consider medical/health wise when chartering a superyacht in the Caribbean

There aren’t any extra medical issues for travelers in the Caribbean but check with your travel agent for any current warnings. The most common are complications form insect bites, jelly fish stings, cuts from coral and heart-related illnesses.

Short List of Caribbean Sailing Yacht Events:

- Antigua Sailing Week – held during the last week of April each year, yachts from all over the world arrive in English and Falmouth Harbours for an action packed week on fun sailing. - St Bart’s Bucket - Grenada Sailing Festival - Heineken Regatta – a Caribbean sailing and party Regatta – The Heineken St Maartens. - Here is the full list of Caribbean yachting and sailing events.

Other Caribbean Places to be:

- New Year’s Eve at St Barts Gustavia, St Martin and the BVI's - More info on Caribbean yachting and sailing events - Please see the Specific Caribbean location links on the left for more.

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CARIBBEAN Yacht Charter Enquiry

Trina, Everything was perfect! The yacht, the crew, activities... The crew in particular was off the charts! They really did go out of their way to please us. Please release the full amount of the gratuity. I have nothing but good things to talk about the charter, an opinion shared amongst all of the guests. Thank you for all your help with the charter of Miracle, everything went smoothly and you were very professional and efficient during the whole process. I will not hesitate in contacting you for our next charter (next year, hopefully!!). Miracle BVI's charter (british Virgin Islands) Caribbean in April

Yachting Destinations Near the Caribbean

Explore Location Guides for great destinations near the Caribbean .

Jost Van Dyke

Yachts for Charter in the Caribbean

112m freire superyacht | from eur€ 3,000,000/wk.

DREAM | From EUR€ 2,000,000/wk

92M FULLY CUSTOM SUPERYACHT | From US$ 1,500,000/wk

93M FULLY-CUSTOM SUPERYACHT | From EUR€ 1,470,000/wk

83m Limited Editions 272 Superyacht | From EUR€ 1,200,000/wk

95 meter CUSTOM | From EUR€ 1,200,000/wk

86M CUSTOM LUXURY YACHT | From EUR€ 1,200,000/wk

SAMSARA | From EUR€ 1,100,000/wk

ROMEA | From EUR€ 1,100,000/wk

80M MODERN CUSTOM YACHT | From EUR€ 1,085,000/wk

SOLANDGE | From EUR€ 1,000,000/wk

PHOENIX 2 | From EUR€ 1,000,000/wk

Caribbean Yacht News

Last minute yacht charter deals in the ...

Benetti launches 34m motor yacht SIRENA ...

Nauta Design reveals details of 35m ...

The caribbean yacht charter specials, special offer location: caribbean.

PARILLION | From US$ 196,000.00/wk

RESILIENCE | From US$ 487,500.00/wk

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AMIGOS | From US$ 250,750.00/wk

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EMERALD | From US$ 168,000.00/wk

Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

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Find Your Perfect Yacht

Caribbean yacht charters - one resource for every luxury charter yacht

The proven resource for crewed yacht charter in the caribbean.

From the moment you contact us, you will be helped by an experienced and knowledgeable specialist who will take the time to understand your unique needs and preferences for your caribbean vacation. They will be your dedicated specialist and our exceptional personal service will answer every question.

The largest choice of crewed Caribbean yachts?

Absolutely, with our relationships built over decades we truly do have access to EVERY crewed private charter yacht based in, or visiting, every part of the Caribbean.

Whatever the type of yacht for your Caribbean charter, your vacation budget, or the size of your party, our specialists will guide you in choosing the ideal yacht for your Caribbean charter. It's your vacation to explore the islands the very best way possible - on a Caribbean charter yacht.

Browse different types of Charter Yachts in the Caribbean

Motor Yachts

This category of Caribbean yachts include mega yachts, super yachts, and all sizes of power yachts. With the maximum space for guests, both inside and out, these types of yachts offer excellent vacations. You can choose from a fast, agile yacht, one that is high-end and luxurious, a yacht with a classic design, or one that is contemporary. This is one of the many choices you’ll have when you plan your vacation. See some yachts:-

Crewed Catamarans are very popular in the Caribbean , especially in the BVIs. Catamarans offer ample deck space that allows everyone to relax together during their charter, sharing the same views throughout the voyage. Caribbean catamarans can typically accommodate between 6 and 12 guests. See some yachts:-

Sailing Yachts

If you are looking for a winter getaway, there is no better place to charter a sailing yacht than the Caribbean! Feel the warm, tropical breeze on your face. Experience the exhilaration as the wind fills the sails and the yacht is suddenly moved along by just the wind. Savor the magnificent beauty of the Caribbean as you sail silently from one island to the next. Although typically offering smaller spaces for guests, sailboats deliver a truly unique caribbean charter vacations . See some yachts:-

Sample Charter Yachts in the Caribbean

ODYSSEA. The 59' sailing catamaran Odyssea is ready to take you and your guests on your next adventure. Throughout she offers relaxing areas to lounge and enjoy the voyage, while enjoying the company of others or absorbing the serenity of the sea. Her spacious cockpit area offers large dining table, sun pad across the back, and wet bar. See ODYSSEA :-

OKTO. Get ready for adventure when you step on board the 217' mega yacht Okto. You and your guests will find plenty to do, as she offers plentiful spaces for lying out to enjoy the sun, enjoying a movie in the circular cinema, working out in the indoor gym with an amazing view, or enjoying the on deck Jacuzzi. See OKTO :-

NAMASTE. The immaculately maintained mega yacht Namaste offers 121 feet of opulence at sea. She features five well-appointed cabins, both a main salon and sky lounge, sundeck with Jacuzzi, gym equipment, and a long list of watersports including jet skis, wakeboard, fishing gear, and the list goes on. See NAMASTE:-

NENNE. The 67' sailing catamaran Nenne was launched in 2017 by Fountaine Pajot, and was given a refit in 2020. With five cabins, she accommodates as many as ten guests, and has an impressive list of water toys that includes water skis for adults and children, wakeboard, standup paddleboards, fishing gear, snorkeling equipment, and the list goes on. See NENNE:-

MARIAH PRINCESS III. The 77' Lagoon built sailing cat Mariah Princess III was built in 2020. She offers two queen cabins and two king cabins, all en-suite. The master cabin has a private deck, the flybridge offers an on deck Jacuzzi, and she has a generous complement of watersports, including onboard SCUBA. See MARIAH PRINCESS III:-

TRUE STORY. The 67' sailing catamaran True Story is ready to give you and your guests a fun and exciting charter in the beautiful waters of the Caribbean. She offers a spacious main salon, large cockpit with al fresco dining and lounge, and flybridge with conversational area. You and your guests can also enjoy a long list of water toys throughout your journey. See TRUE STORY:-

The British Virgin Islands include Tortola, Jost Van Dyke, Virgin Gorda, and more. There’s no better way to experience the waters and beaches of the BVI's than on a private Caribbean charter with a full crew to pamper you. Of all the islands in the Caribbean, the Virgins are furthest north. This makes them very convenient due to the proximity to San Juan and due to their direct flights from the United States. Catamaran sailing vacations and crewed sailing charters are very popular in the islands, and their protected waters make them a favorite spot for guests that are taking their first private Caribbean yacht charter. To learn more about them:

The U.S. Virgin Islands consist mainly of the three large islands of St. Thomas, St. Croix, and St. John. With lovely bays, long beaches, lush nature preserves, fabulous diving spots, and excellent, onshore evening entertainment, many choose to vacation in the USVI’s. Caribbean charters often visit both the BVI’s and USVI’s during the same week, as they are close to one another and the waters are generally calmer than in other parts of the Caribbean. They in general are also home to the largest fleet of crewed, all-inclusive, luxury catamarans. To find out more about them:

The Leewards are situated in the middle of the Caribbean Island chain. The major airports are located on St. Maarten and Antigua. Due to the English, Dutch, and French influences everywhere you look, they exhibit the best example of cultural sophistication anywhere within the Caribbean. If you are looking to see where the rich and famous go on vacation, you will want to visit the island of St. Barts; for many this is a must stop for a Caribbean yacht charter. Many mega yachts are available for rental in St. Maarten, as it has become a popular mega yacht Caribbean base for the winter. To learn more about the Leewards:

The Grenadines are also called The Windward Islands. Oftentimes our guests will choose a sailing charter over a motor yacht when in the Grenadines, due to the more constant tropical breezes that occur. The islands are much less developed than the rest of the Caribbean, and the inhabitants live on their own time schedule, which enhances the feeling of getting away. The northern most island accessible by air is ST. Vincent, while the southern tip’s major airport is on Grenada. There are fewer Caribbean charter yachts based here; however, occasionally some charter yachts are happy to relocate in order to offer a vacation that happens a little off the beaten path. To find out more about the Grenadines:

What Type of Charter Yacht?

There are all types of Caribbean yacht charters available, including mega yachts, power yachts, catamarans, and sailboats. We have helped countless clients choose the right charter yacht, learning what features and amenities make a difference on caribbean charter yachts. Learn more about different types of Caribbean yachts.

Where Can You Go?

Typically you’ll choose between the Virgins, Leewards, and the Grenadines to charter your yacht. Beyond the region, it is your Caribbean to explore. It’s important for you to remember that there is no cruise ship itinerary to worry about! Your itinerary will be custom designed specifically for you, with you, and is flexible to changes during your charter. We have put together some samples for you to get an idea of what you might like to do while on vacation in the Caribbean. Interested in seeing a sample cruise itinerary ?

Find Your Perfect Yacht for a Caribbean yacht charter

To see the Caribbean yachts we have in our online database, please select a yacht type and your budget below. Please keep in mind that we do not have every available yacht online. There are many more yachts available for you to choose from when you contact one of our specialists.

For your personalized selection including yachts not online:- Email us now

Caribbean Charters - When To Go.

One of the lovely things about the Caribbean is that the temperatures remain consistent throughout the year; however, there are some other weather considerations that you will want to factor in when making your caribbean yachting vacation plans. Read More....

Vacations here are most popular between November and July.

If you are thinking of a megayacht, you will want to keep in mind that many of these private yachts which are Caribbean based in winter leave in the late spring and early summer months. They will return again in early winter; however, this does limit their availability. To charter a mega yacht, you will want to make sure that you do so well in advance.

Motor, sail, or catamaran yachts, on the other hand, often have selections available year round. Holidays like Christmas, New Year’s, and Easter do need to be planned for as early as possible as these are very popular charter times.

The availability for Caribbean charters can also be affected by the weather in other climates, for instance, when the severity of the weather is bad in the United States or Europe, especially between January and February, the charters are often booked. This is due to many clients looking for a break from the cold.

What Do Our Clients Say About The Caribbean?

Are you excited yet? You should be! Our clients have enjoyed fantastic Caribbean vacations. There is an endless number of places to visit in the Caribbean, from smaller islands to absolutely must be seen locations like St. Barts. Read some of our Caribbean charter reviews from clients who booked a Caribbean charter with us.

Ready to learn more about Caribbean charters?

We are specialists who will make your trip a reflection of our expertise! We know clients need to be confident in their charter vacation plans, so we encourage our clients to benefit from the knowledge base we’ve been building for years. You’ll speak to an authority on Caribbean charters without any obligation on your end.

Test our expertise with your questions!

Contact a specialist - available 7 days a week.

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Color and Contrast: the Complete Sailboat Vacation

Simply the perfect place to take a bareboat or skippered sailing holiday. Such a diverse collection of islands dotting the clear blue sea, each with its own unique appeal. Local cultures that fascinate and entertain, offering a welcome that keeps charterers returning to these waters year after year. With its 7,000 Islands and 28 Island nations, reliable trade winds and long sailing season, the Caribbean is a region that offers an endless amount of holiday enjoyment.

At Sail Connections, we work with all the best charter operators in the Caribbean, sorting through all the available boats and presenting all the best options to suit your vacation plans. Some of our operators offer extra services that are unique to their destinations. We personalize your proposal and give you the benefit of our knowledge and local contacts, to deliver a fabulous sailing holiday wherever there's a boat to charter in the Caribbean. 

Charter Sailing in the Caribbean

The Caribbean's numerous islands give you so many fabulous places to explore, so many diverse cultures to experience, that the permutations for planning a sailing charter are simply too numerous to list. The sailing distances between territories can be very short, and there are countless yacht charter bases scattered across the region. That opens the door to all manner of opportunities – from a seven-day sail around one distinct island nation to a multi-week one-way charter that takes in a wide variety of cultures and geographical features.

The Caribbean yacht charter season is busy from November through July. The peak season is mid-December to March, when winter escapees from North America and Europe arrive in their greatest numbers.

The hurricane season arrives late July and can last until early October, although storms here are rare and tend to deflect northwards towards the USA rather than hit the Caribbean. These months have their advantages in that they are the least costly for chartering, particularly in the British Virgin Islands. At that time of year it is in fact more likely to encounter light winds than it is storms.

As with many yacht charter locations, the shoulder season can be the best time to charter a yacht. In the Carribean that's from April to July. There are less shore-based visitors then, yet you can expect settled and sunny weather with warm, steady breezes prevailing.

We have access to over 30 charter bases in the region, from where you can take a sailboat vacation like no other. We select from the best boats available and guide you into the ideal sailing adventure that matches your interests and level of experience. The sailing options here are just about endless. Hopefully these pages will help you on your way to your much-anticipated Caribbean sailing holiday.

Regional Map of the Main Charter Sailing Areas

A One-way Cruise: Martinique to Grenada

There are quite simply countless itinerary options for sailing the caribbean. for many charterers a downwind cruise offers the crew conditions for maximum enjoyment. so here's a sample north to south course plan that gives you the prevailing breeze abaft. .

Waterfront at Fort de France, Martinique's largest town

Sailing from Martinique to Grenanda you can expect winds primarily from the northeast, especially around peak season either side of Christmas. Sailing this course involves short stretches of open water, with a stiff and steady breeze on your aft quarter. That makes for quick passages with most enjoyable sailing to a choice of Islands, whether it be for a lunch stop and a snorkel, or an overnight stay.

The eastern Caribbean islands that form a distinctive arc on the map are collectively the Lesser Antilles, a mixture of soverign states and territories governed by various powers. A trip along some of this chain exposes the voyager to a wide variety of cultures and customs in places that all sit in the idyllic picture-postcard surroundings of the movies and travel brochures. 

Starting in Martinique and sailing south, you are exploring the Windward Island group of the Antilles.

Wildlife viewing at its finest in the Tobago Cays

Like most of this group, Martinique was orginally colonised by France, and French flair is still in evidence there today. Martinique offers excellent on-shore facilities for the visitor, and is a popular base for boat charters. The island is mountainous, but with plenty of white sandy beaches to enjoy, especially in the south.

The next island is St Lucia. It's some 30 nautical miles to Rodney Bay on St Lucia's northwest, so to get there requires an early start. There are several top spots to visit down the island's sheltered western coast. Take time out to investigate Les Deux Pitons.

Another long but relaxing sail to St Vincent and the Grenadines, so-named because of their joint French and British colonial history. St Vincent has its Blue Lagoon that you'll probably overnight in, while the Grenadines island group, some of which confusingly belong to Grenada, provide numerous anchoring options.

Happy charterers enjoying their time ashore in the Grenadines

The Grenadines stretch all the way to Grenada, your final port of call, making this part of the voyage very convenient for a leisurely sail. Call in at one of the uninhabited Tobago cays for a real taste of desert island living, if only for a few hours.

Once offshore Carriacou you are in Grenadan territory. Grenada, like St Lucia & St Vincent and the Grenadines, is now an independent member of the British Commonwealth, but with historical French influence. This is the 'Island of Spice' where nutmeg and mace production are important to the economy. As is tourism, and there is plenty to entertain you before concluding your vacation and departing these fabulous sailing waters.

Once you have experienced all the pleasures of sailing the Caribbean, chances are you'll be back one day for more.

The Best Caribbean Charter Sailing Destinations

British Virgin Islands

US Virgin Islands

Puerto Rico & Spanish Virgin islands

Cayman Islands

St Martin, St Barts, Anguilla, St Kitts & Nevis

Antigua & Barbuda

Martinique, St Lucia & The Grenadines

Latest Blog Posts

Charter catamarans for modest sailing holiday budgets

Here we highlight some smaller catamarans finding favour with our charterers in the Mediterranean and elsewhere. Robert is our expert evaluator when it comes to helping you select the right boat for your sailing charter, and the following is his personal take on recent introductions to the charter boat market.

The popular Bali Catamaran in all its variations

The Bali catamaran, designed and built specifically with chartering in mind, has become so popular that it’s been hard to keep up with all the new models, hard to spot which one has just the right size and amenities to perfectly fit your group's sailing holiday charter needs. We can help you there.

The value of after-charter destination and boat reviews

At Sail Connections we offer a personal service based on long experience in the business and close attention to what's happening in the destinations we offer. We have also sailed a large number of those places, and can often speak from personal experience.  But we can't be everywhere.

Chartering in Turkiye: feedback we just have to share

Turkey is one of those charter destinations that doesn't fail to pleasantly surprise. We're always delighted when we receive such good reports as we did recently from a New Zealand client.

Barcelona gets ready for the America’s Cup

As well as the competition for the Auld Mug itself, the 37th America’s Cup in Barcelona will incorporate the first ever Women’s and Youth America’s Cup regattas. Chartering Barcelona 2024 will be in demand!

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We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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LUXURY YACHT CHARTERS & SAILING VACATIONS

All-Inclusive Yacht Charters

All-Inclusive Yacht Charters are with a captain and your own personal chef they tailor your charter for a needs and requests. allows you enjoy sailing in beautiful large vessels such as; Catamarans, Monohulls and Power Yachts designed for comfort.

Kayak, snorkel, sail, scuba dive, paddle-board, fish, island hop, or simply relax aboard a Caribbean yacht charter. We’ve listed just a few reasons below:

Fully Crewed, Catered & Private Sailing Yacht Charters Tailored for You & Your Guests

• Private Sailing Vacation
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• Visit Untouched Islands
• Different Caribbean Destinations
• Unforgettable Memories
• Fully Prepared Meals by Your Own Private Chef
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We Look Forward to Welcoming You Aboard!

Explore Destinations like the British Virgin Islands, St. John, Grenadines, Bahamas, and St. Marten!

All-Inclusive Yacht Charters are with a captain and your own personal chef they tailor your charter for a needs and requests. allows you enjoy sailing in beautiful large vessels such as; Catamarans, Monohulls and Power Yachts designed for comfort.  For more information, please visit our: Frequently Asked Questions.

Choose a vessel from our inventory:

FEATURED YACHT CHARTERS

• Sleeps 12 Guests
• 7 Kings, 1 Twin

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• 2 Doubles, 2 Twins, 2 pullman

• Sleeps 8 Guests
• 3 Queens, 1 Twin

BLUE HORIZON

• Sleeps 6 Guests
• 2 Kings, 1 Queen

POPULAR YACHT DESTINATIONS

Other Yacht Charter Destinations

• Florida Key’s
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• British Virgin Islands

DAY CHARTER BOAT RENTALS

Scout in the Virgin Islands

Full-day charters 9:30 – 4:30 PM. US Virgin Islands or the British Virgin Islands $1800. Bar hop or visit exclusive beaches while you stop and snorkel along the way!

Our 38′ Scout comfortably holds 6+ passengers, allowing plenty of room to lay out on the sun deck or relax in the shade while enjoying a drink and listening to your favorite music.

1/2 Day or Full Day Charters

• Captain and Crew
• Complementary snorkel equipment and fins
• Coolers stocked with Ice, water and assorted beer.
• Abundance of cushioned seating and lounging areas in shade or sun.
• Dry storage for your personal items and gear.
• Full size restroom
• All required USCG approved safety equipment, and extra features not required by law.
• Food, Liquor, Fuel and Crew Gratuity is NOT included.

Fishing in the Virgin Islands

Everyday is a great day to book a fishing excursion. We can give you the fishing trip of a lifetime. Whether you are an experienced fisherman or just getting started the  mahi-mahi, tuna, wahoo, and big marlin await.

We have all the latest and best fishing gear, outriggers, navigation and sonar, along with some of the best and most experienced captains in the islands. Whether you choose a half day (3.5 hours) or a full day (7 hours) off shore trip, you’re guaranteed to have a good time.

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771  Crewed Luxury Yachts for Charter in the Caribbean

• Caribbean Yacht Charter

A Caribbean yachting vacation incorporates vast expanses of crystalline waters and endless clusters of idyllic paradisical islands, making for a picture-perfect family getaway. With its beautiful climate and spectacular coastlines that comprise iconic superyacht hotspots like the  Virgin Islands ,  St Barts  and  Antigua , a yacht rental in the Caribbean has an alluringly evergreen appeal.

Caribbean Yacht Booking Guide:

Caribbean Yacht Charters: At a Glance

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The Caribbean Sea comprises more than 7,000 islands, islets, reefs and cays, and is divided into three island arcs: that of the Greater Antilles in the north, the Lesser Antilles in the south, and the Leeward Antilles to the east.

• Ideal winter destination Boasting all-year-round pleasant weather, its powdery sand beaches and alluringly clear waters make it an especially popular choice for winter yacht charters.
• Easy-to-reach The Caribbean is well-connected to the US, with a high number of international airports flying directly into the region.
• Secluded anchorages With more than 7,000 islands and only a small percentage being inhabited, the world is your oyster when it comes to finding serenely beautiful anchorages.
• Snorkeling and diving paradise The Caribbean is home to some of the world's most impressive snorkeling and diving sites, meaning plenty of exciting underwater adventures where your eyes will be wide with wonder.
• Excellent superyacht marinas The Caribbean has numerous well-provisioned superyacht marinas to take your pick from, many of which have fantastic dining and shopping opportunities.

While the Bahamas is technically part of the Caribbean region, it is an island nation in its own right, forming part of the Lucayan Archipelago in the Atlantic. That said, the Caribbean is a vast area occupied by thousands of islands, coral reefs and islets, of which the Bahamas forms a part, along with strong political and cultural ties that have created a natural bond with its Caribbean neighbour. 

Practically speaking, however, if you are interested in cruising  the Bahamas  in conjunction with your Caribbean yacht charter, it is highly unlikely you'll be able to manage the distance during a typical 7-day charter, especially for itineraries that incorporate East Caribbean destinations such as Antigua and Saint Martin. You will need to decide which destination you prefer to spend your time in, or extend your charter vacation to incorporate both. 

To find out more about chartering in the region, check out our in-depth Bahamas destination guide for more information.

The most popular destinations for renting a yacht in the Caribbean are those located in the Lesser Antilles region, primarily the island groups of the Leeward Islands.  and the  Windward Islands .

For Leeward Island yacht rentals , Antigua, the Virgin Islands, St Martin, St Barts and St Kitts and Nevis garner the most attention, thanks to not only their splendid tropical landscapes but also their extremely well-provisioned superyacht marinas, fine dining options, impossibly hip bars and medley of designer boutiques bound to keep guests entertained from dawn till dusk.

Scattered like pearls along the aquamarine seas, you'll find sun-drenched Martinique, gorgeous Grenada and the ultra-secluded St Vincent and the Grenadines  are the top picks for slow-paced  Windward Island yacht charters .

Although not as popular, the islands that form the Greater Antilles , such as Jamaica, Cuba and Puerto Rico , are just as beautiful and offer an array of spectacular destinations to explore and discover on a luxury yacht charter.

Looking for the best superyacht hotspots in the Caribbean? These are the spellbinding locations guests find most enticing. If you are interested in any of these cruising grounds, we strongly advise booking as far in advance as possible.

• Antigua: the jet-set adore its unbelievable scenery, intriguing historical landmarks, lavish shopping options and a cluster of ivory-white sands coupled with gin-clear waters.
• St Martin/Sint Maarten : French and Dutch sides of the island combine to bring a fascinating fusion of influences, replete with outstanding diving spots and awe-inspiring topography. 
• St Lucia : considered the tropical jewel of the Windward Islands, it's virtually unspoiled. Bordered by lush rainforest and dark volcanic sands, it makes for a truly unique anchorage spot. 
• Grenada : known as the Isle of Spice thanks to being one of the world's largest exporters of mace and nutmeg, its capital St George is regularly called the Caribbean's most picture-perfect town. 
• St Barts : Well-known for its moniker "St Moritz of the Caribbean" due to its unique Swedish-French colonial heritage, this iconic tiny island is synonymous with glamour, movie stars and designer shopping. 
• St Croix, US Virgin Islands : The largest of the USVIs boasts a National Park, breath-taking scenic beauty and some of the best dive spots in the Caribbean.
• Puerto Rico : Affectionately known locally as the ‘island of enchantment’, Puerto Rico is a profusion of vibrant Latin culture entwined with the laid back rhythm of the Caribbean, with pristine beaches, excellent diving spots and exquisite local dishes.

A yacht rental vacation in the Caribbean delights guests with its truly endless number of things to see and do. Here are our top picks:

Don't Miss:

• Eden Rock St. Barts : one of the most in-demand hotels in the Caribbean, with a seven-star bar and spa.
• Hermitage Bay, Antigua : kick back and relax on this tropical beach that delivers on sensational views.
• Bagatelle, St. Barts : overlooking the glittering Gustavia harbor, this sophisticated bar and restaurant is a hugely popular superyacht spot, showcasing the finest of French-Caribbean cuisine.
• Basil's Bar, Mustique : legendary bar and restaurant designed by Philippe Starck, frequented by royals, supermodels and rockstars for decades.
• The Cotton House, Mustique : a wellness center unsurpassed in beauty.
• Watermelon Cay, St John, US Virgin Island s: dreamy islet surrounded by coral reefs and a veritable snorkeling wonderland
• Rhone Marine Park, British Virgin Islands : the wreck of the RMS Rhone is the BVIs' most popular dive site, and arguably one of the best in the Caribbean.
• Trunk Bay, St John, US Virgin Islands : all dazzling white sand lapped by the bluer-than-blue ocean, this island paradise ranks consistently among the world’s top 10 beaches.
• Jardines del Rey archipelago, Cuba : known locally as the ‘King’s Gardens’, this collection of islands is a registered UNESCO Biosphere Reserve and an island-hopper's paradise, offering myriad secluded beaches and sensational sunsets.

For anyone looking to get a dose of serious sunshine during the Northern Hemisphere winter, a yacht charter in the Caribbean is a seriously enticing prospect, with St Barts being the clear favorite for Christmas and New Year's Eve, thanks to the showstopping celebrations that take place in Gustavia Harbour.

For avid island hoppers, the Windward islands offer an enchanting itinerary full of sun-kissed isles and laid back charm juxtaposed with chic resorts and heavenly French-based cuisine, not to mention unrivalled vistas and sultry sunsets accompanied by warm rum-laced winds. 

Across all Caribbean destinations, keen divers and snorkelers will be in for a subaquatic treat, and you'll find a wide range of designer boutiques and ultra-high-end resorts peppered across the isles wherever you go.

The Caribbean is a mesmerizing melting pot of cultures and influences, rooted in its rich heritage and undeniably shaped by its history of colonization and waves of immigration. Each island group is highly diverse in terms of its language, music, customs, architecture and cuisine, but it's mainly English, Dutch, French or Spanish colonial influences that are keenly felt. While the mix of languages spoken will differ between island groups, English is widely spoken.

Caribbean cuisine sees influences from Africa, Europe, Latin America and Spain, Meat, seafood, coconut, potatoes, beans and tomatoes tend to feature heavily in local dishes.

Locals are friendly and regularly celebrate their culture, with music, food and wildly colorful festivals held throughout the year.

A luxury yacht rental vacation in the Caribbean is, without doubt, the most sublime way to experience this region, giving you exclusive access to heavenly anchorages that are otherwise impossible to reach or are far from the typical tourist trail.

Guests have boundless fleet options when it comes to a crewed Caribbean charter. If you don't know whether to go for a motor yacht, sailing yacht or catamaran to cruise Caribbean waters, we've laid out the main points worth considering.

Motor Yacht Charters in the Caribbean

A  luxury motor yacht charter  in the Caribbean is a seven-star way of uncovering the epic beauty of the Caribbean in total privacy. 

For regions with minimal water depth the ideal choice is a motor yacht with low draft, perfect for accessing shallow lagoons and secluded bays.

For those who have their heart set on a superyacht without a shallow draft, dropping anchor further out into deeper waters and then getting a tender ride ashore, so you can get up close and personal to exquisite island reefs and blue lagoons, is the preferred option.

Sailing Yacht Charters in the Caribbean

Chartering a sailing yacht in the Caribbean is ideal for guests looking for a slower pace to fully lap up the Caribbean rays with more outdoor deck space, and add a little old-school charm to their cruising adventure.

Even better, the majority of sailing charter yachts come equipped with a retractable keel, meaning reaching turquoise shallows is a breeze. But, if you are keen to charter a larger sailing yacht, keep in mind that some may still find their draft too deep for some areas, even with the keel up. 

Catamaran Charters in the Caribbean

Luxury catamaran charters are a firm guest favourite for those embarking on Caribbean vacation, especially in the Bahamas and the Virgin Islands. Thanks to their shallow draft, catamarans give you the ability to get close to cays and islets guests can savor the thrilling feeling of being able to jump off-board at almost any point. 

The charter cost of a motor yacht, sailing yacht or luxury catamaran rental in the Caribbean will vary according to the vessel's size, age, type, number of crew, as well as the location and duration of the vacation as well as the season it takes place. 

With so many options available, there’s something to suit every type of budget. For convenience we have listed the average prices for motor yacht and sailing yacht charters in the Caribbean below;

• For motor yacht rentals in the Caribbean, prices can range from $39,167 to $1.4m per week, plus expenses
• For luxury sailing yacht rentals in the Caribbean, prices can go from $29,855 to $276,495 weekly, plus expenses

The best time for luxury yacht charters in the Caribbean is between November and March, when guests can expect clement weather and vividly blue cloudless skies.

Another aspect to keep in mind is that this is also the time when you will have the largest selection of yachts to choose from, as most charter yachts descend on the Caribbean around November after the Mediterranean season has ended and any yacht maintenance has been carried out, before returning back to the Mediterranean in March/April.

The most popular starting point for a Caribbean yacht rental is usually in either Saint Martin/Sint Maarten or  Antigua,  both of which have international airports.

It is certainly possible to begin your charter in other Caribbean destinations, providing this has been agreed with the Owner and charter broker .

Where to End a Caribbean Yacht Charter

For most private Caribbean yacht charters, there isn't one definitive place where to disembark given the vastness of the region. However, what is likely is that you will finish your yacht rental vacation in the same location that you started. For example, the majority of  British Virgin Island yacht charters will begin and end in St Thomas, while for Antigua yacht charters , it'll be the iconic English Harbour.

sample itineraries

The Caribbean offers some of the most spellbinding berthing spots in the world. These tropical, barefoot hotspots are of the finest calibre, surrounded by jaw-dropping scenery, and often feature award-winning restaurants, hip boutiques, beach bars and more.

But which marinas are the best? Below are some charter favorites:

• Falmouth Harbour, Antigua: impressive marina facilities and scenery, catering to yachts up to 100m.
• Marina Fort Louis, Saint Martin: offers 150 berths for yachts up to 79m.
• Crown Bay in St Thomas (USVI): full-serviced marina with 99 slips, including 16 berths for superyachts up to 60m
• Port Louis Marina, Grenada: idyllically located, with 227 moorings for yachts up to 91m.
• Port de Gustavia, Saint Barts: widely regarded as one of the most beautiful natural harbours in the world, accommodating up to 152 yachts up to 152m.
• Puerto Del Rey, Puerto Rico : conveniently located as a jumping off point for yacht charters incorporating the Virgin Islands and Lesser Antilles, this marina has plentiful wet slips, including capacity for yachts up to 200ft (60m) LOA.

We strongly advise booking through a qualified  yacht charter broker at least three months in advance for all Caribbean yacht charters. By doing so, you will increase the likelihood of securing your preferred dates and you will have a greater selection of yachts on offer to choose from.

This also ensures your yacht broker has enough time to craft a carefully curated itinerary and secure an overnight berth in the most popular Caribbean marinas.

related articles

Start Planning - Speak with a Charter Expert

Our yacht charter experts will:

• Discuss your vacation plans
• Check availability & shortlist suitable yachts
• Negotiate booking & prepare your itinerary

Need Advice?

Speak to a Charter Broker

Explore the Caribbean

Guide to Bahamas

Guide to Virgin Islands

Guide to Leeward Islands

Guide to Windward Islands

Guide to Greater Antilles

Guide to Turks & Caicos Islands

Guide to Barbados

Guide to Trinidad & Tobago

The caribbean yacht charter itineraries.

Make every moment count during your superyacht vacation with our carefully curated yacht charter itineraries, tailored so you can experience the very best of the paradisiacal islands of the Caribbean and ensure your yacht charter is a truly memorable one. Designed by yachting experts, we've cultivated itineraries that will satisfy a range of requirements.

For yacht charter guests seeking a little glitz and glamour on their vacation, a 7-day charter around the Leeward Islands is a must, comprising Caribbean gems such as Saint Barthelemy, renowned for its A-list celebrity culture and designer shopping, as well as the perennial favourite Antigua. For sheer unadulterated bliss, incorporate the Virgin Islands on a 14-day yacht charter, promising idyllic stretches of pristine sands lapped by waters in every shade of blue.

Discover the Caribbean

Winter Getaways, Tropical Paradise Islands, Snorkeling & Scuba Diving, Crystal Clear Waters, Beautiful Secluded Anchorages, Well-Provisioned Superyacht Marinas

When to Go:

December - March

International Airports:

• Princess Juliana Airport (St. Maarten)
• V.C. Bird Airport (St. John's, Antigua)
• Luis Muñoz Marín Airport (Carolina, Puerto Rico)
• Grantley Adams Airport (Bridgetown, Barbados)
• Lynden Pindling Airport (Nassau, The Bahamas)

Luxury Yachts for Charter in the Caribbean 2024 & 2025

Crewed charter yachts in the caribbean.

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92m   Neorion

from $1,070,000 p/week ♦︎

115m Lurssen

115m   2021

from $2,809,000 p/w eek ♦︎

Black Pearl 14

105m Oceanco

105m   2018

Christina O 34

99m Canadian Vickers

99m   1943/2020

from $756,000 p/w eek ♦︎

Carinthia VII 12

97m Lurssen

97m   2002/2023

from $1,519,000 p/w eek ♦︎

97m Feadship

97m   2017/2022

from $1,736,000 p/w eek ♦︎

Madsummer 12

95m Lurssen

from $1,297,000 p/w eek ♦︎

93m Feadship

from $1,513,000 p/w eek ♦︎

Aquarius 12

92m Feadship

from $1,500,000 p/w eek

Queen Miri 36

92m Neorion

92m   2004/2023

from $1,070,000 p/w eek ♦︎

Lady Lara 12

91m Lurssen

91m   2015/2023

from $1,400,000 p/w eek

90m Corsair Yachts

90m   2007/2021

from $497,000 p/w eek

90m Oceanco

from $1,302,000 p/w eek ♦︎

89m Oceanco

from $1,100,000 p/w eek

89m   2015/2023

Maltese Falcon 12

88m Perini Navi

88m   2006/2023

from $490,000 p/w eek

86m Scheepswerf Gebr. van der Werf

86m   1998/2024

from $535,000 p/w eek ♦︎

Man of Steel 12

86m Oceanco

86m   2010/2023

from $1,000,000 p/w eek

O'Ptasia 12

85m Golden Yachts

85m   2018/2022

from $972,000 p/w eek ♦︎

Victorious 12

85m Ak Yachts

from $864,000 p/w eek ♦︎

Le Ponant 32

84m   1990/2022

from $492,000 p/w eek ♦︎

Savannah 12

84m Feadship

84m   2015/2020

from $1,081,000 p/w eek ♦︎

Alfa Nero 12

81m Oceanco

81m   2007/2021

from $728,000 p/w eek *

Sea Eagle 11

81m Royal Huisman

81m   2020/2022

from $597,000 p/w eek ♦︎

Elements 12

80m Yachtley

Excellence 12

80m Abeking & Rasmussen

from $1,150,000 p/w eek

Amaryllis 12

78m Abeking & Rasmussen

78m   2011/2022

from $770,000 p/w eek

78m Golden Yachts

78m   2023/2024

from $810,000 p/w eek ♦︎

from $480,000 p/w eek

Stad Amsterdam 28

76m Damen Oranjewerf

76m   2000/2009

from $102,500 p/w eek

Huntress 12

76m Lurssen

from $725,000 p/w eek

75m Admiral Yachts

75m Feadship

from $900,000 p/w eek *

75m Abeking & Rasmussen

from $880,000 p/w eek

from $987,000 p/w eek ♦︎

74m Nobiskrug

74m   2008/2013

from $562,000 p/w eek ♦︎

73m Delta Marine

73m   2006/2015

from $525,000 p/w eek

Nautilus 12

73m Picchiotti

from $809,000 p/w eek ♦︎

73m Lurssen

73m   2006/2020

from $615,000 p/w eek

Quantum of Solace 12

73m Turquoise Yachts

73m   2012/2022

from $574,000 p/w eek

Game Changer 17

72m Damen Yachting

72m   2017/2020

from $450,000 p/w eek

72m   2010/2023

from $600,000 p/w eek

72m Dunya Yachts

72m   2013/2020

from $660,000 p/w eek

Talisman C 12

71m Turquoise Yachts

71m   2011/2020

from $567,000 p/w eek

70m Feadship

from $650,000 p/w eek

Sherakhan 26

70m Vuijk Scheepswerven

70m   2005/2022

from $591,000 p/w eek ♦︎

Sycara V 12

68m Nobiskrug

68m   2010/2017

Wayfinder 12

68m Astilleros Armon

from $375,000 p/w eek

68m Icon Yachts

68m   2010/2020

from $540,000 p/w eek

67m Benetti

from $680,000 p/w eek

67m Shadow Marine

67m   2007/2008

from $120,000 p/w eek

67m Alloy Yachts

67m   2011/2019

from $351,000 p/w eek ♦︎

66m   2014/2023

66m Rossinavi

from $637,000 p/w eek *

Invictus 12

66m Delta Marine

66m   2013/2020

from $650,000 p/w eek *

65m Benetti

Ventum Maris 12

66m   2011/2021

from $530,000 p/w eek

Eternity 17 7 12

65m Codecasa

65m   2010/2022

from $390,000 p/w eek

Illusion 12

65m   2013/2019

from $462,000 p/w eek

Resilience 12

from $648,000 p/w eek ♦︎

Silver Angel 12

65m   2009/2015

from $425,000 p/w eek

64m Benetti

64m   2016/2021

from $475,000 p/w eek

63m Halter Marine

63m   1978/2022

from $350,000 p/w eek *

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Crewed Luxury Yachts in the Caribbean

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A charming beacon of hope in the Bahamas

Paradisacal nature park in the Bahamas

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Caribbean Yacht Charter Q&A

The best time to visit the Caribbean is generally December to April, when it's a little cooler and less humid. But the best month to visit can differ depending on the island, budget and interests you have. For example, some yacht charter guests may decide to visit May to June and late November, when weather is still fantastic but there are fewer crowds.

We advise booking your Caribbean yacht rental at least three months in advance to ensure you get the yacht you desire. The longer you leave it, the fewer choices you will have to rent in the Caribbean.

For your Caribbean superyacht charter, you will need to provide a completed charter agreement and 50% of the charter fee as a deposit. This is payable once the contract has been signed.

When booking a Caribbean yacht rental, do keep in mind the costs that aren't included in the base rate, namely VAT and the APA (Advance Provisioning Allowance). The APA is usually paid in advance of the charter and is commonly set at 30% of the charter fee. This allowance covers expenses such as fuel, berthing, food and drinks, as well as any special requests. 

Please consult your yacht charter broker for any other costs you may need to factor in for your yacht charter in the Caribbean.

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YachtCharterFleet makes it easy to find the yacht charter vacation that is right for you. We combine thousands of yacht listings with local destination information, sample itineraries and experiences to deliver the world's most comprehensive yacht charter website.

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Discover Paradise in St Vincent & the Grenadines

Premier Sailing School offered weekly

Bareboat or with a Captain - the choice is yours !

Welcome to Barefoot Yacht Charters

Caribbean Bareboat Sailing Charters The Barefoot Lifestyle – No Shoes, No Stress, No Mess Ph: +1-784-456-9334

Neptune Fleet

Discover the epitome of seafaring indulgence with Barefoot Yachts’ Neptune fleet, meticulously outfitted and maintained for discerning adventurers. Our luxury comfort yachts redefine relaxation, boasting opulent amenities and spacious layouts, ensuring an unrivaled at-anchor experience. Immerse yourself in tranquility and luxury as you cruise the pristine waters of the Grenadines. On the other hand, our luxury performance fleet stands as a testament to superior sailing, designed to thrill and delight enthusiasts seeking exhilarating voyages. Sail with precision, power, and grace, embracing the wind and waves like never before, reveling in the exciting sailing conditions for which the Grenadines are famous. Barefoot Yachts, a boutique family-owned charter company, invites you to savor the finest in nautical luxury.

Viewfinder 2020 Bali 4.1

Ulysses Lagoon 42

Sonhos Bali 4.4

Hearts Desire Lagoon 46

Catara NEEL 43

AONYX O-Yacht 45

Navigator fleet.

Embark on a cost-effective voyage without compromising luxury aboard Barefoot Yachts’ Navigator fleet, featuring 5-year-old and older sailing yachts. Choose from our distinct categories: luxury comfort yachts, tailored for an idyllic at-anchor escape with opulent amenities, or luxury performance yachts, finely tuned to deliver thrilling and memorable sailing journeys. Experience the blend of affordability and elegance as you navigate the beautiful waters, soaking in the sunsets and salty breeze. Barefoot Yachts, a cherished boutique family-owned charter company, invites you to relish an unmatched balance of economy and indulgence on the high seas.

Willow Dew Lagoon 39

Rob Roy CATANA 531

Pelican Pete Sun Odyssey 34

Lady Di Oceanis 41

Inordinate Venezia 42

Betty Blue Beneteau 50

Fully crewed yachts.

Experience unparalleled opulence aboard A Barefoot Yachts’ fully crewed private luxury yacht charter, where desires are effortlessly met by an attentive crew dedicated to pampering guests with first-class service. Indulge in delectable gourmet meals prepared by your private chef and revel in the freedom to sail on your schedule. With over 32 years of navigating the Grenadines, Barefoot Yachts offers a unique understanding of the region, ensuring an exclusive journey through these breathtaking waters, enriched by their expert insight into the cruising grounds and the vibrant local culture.

Splendido Beneteau 57

Racing fleet.

Embark on a sailing adventure of a lifetime with Barefoot Yachts’ race charters in the Caribbean! Picture yourself on the tiller of a professionally maintained, high-performance sailboat, cutting through the azure waters of the Caribbean. Experience the exhilaration of competitive racing and join the ranks of international sailors, embracing the thrill of challenging race courses set amidst the incredible beautiful of these iconic islands. Revel in post-race festivities under starlit Caribbean skies, sipping fine local rums and dancing to the rhythm of this vibrant paradise. Unleash your inner competitive sailor and experience some of the best grand prix racing events in the world, with Barefoot Yachts.

SALT FISH J 24

HAPPY Melges 20

SMILE (#212) Melges 20

GONE C&C 30

SEAPLANE Melges 32

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The Barefoot Lifestyle

At Barefoot, our philosophy is simple and our lifestyle is sweet. Through our commitment to you experiencing your ultimate vacation, clean sailing, our use of locally produced organic provisioning and our responsible operating practices, we hope to protect and enhance your experience while improving the world we share with all living things.

Driftwood Restaurant/Bar

Driftwood Restaurant offers Mediterranean cuisine with a Caribbean flair, a stunning seaward view of Blue Lagoon and an intimate, air-conditioned lounge bar. We specialize in local, organically grown fruits and veggies.

Caribbean Bareboat Sailing Charter Videos

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CARIBBEAN YACHT CHARTERS

Caribbean yacht charters, is synonym to tropical paradise and an excellent sailing destination. White sandy beaches, clear waters and palm trees make Caribbean bareboat charter an unforgettable sailing experience. Islands surrounded by the Atlantic Ocean and Caribbean sea, provide numerous destinations.

Rent a Boat in Caribbean: 1300 Available

Robertson caine 51 pc power boat charter (2015).

from 02-Mar to 09-Mar 24

Rent a boat Oceanis 43 (2009) in Grenada

from 09-Mar to 16-Mar 24

Sailboat Dufour 412 GL (2018) for rent in Antigua

from 17-Aug to 24-Aug 24

Dufour 412 GL sailboat charter (2018)

Rent a boat Dufour 390 GL (2019) in Guadeloupe

Sailboat Dufour 425 GL (2012) for rent in Antigua

from 01-Jun to 08-Jun 24

Dufour 460 GL sailboat charter (2018)

Rent a boat Dufour 460 GL (2018) in Guadeloupe

Sailboat Dufour 390 GL (2019) for rent in Antigua

Oceanis 41.1 sailboat charter (2018)

Caribbean Yacht Charter Reviews with 12knots

Sally McLaughlin

“Everything was perfect”

Everything was perfect from start to finish. Responses to my questions were fast, clear and reliable. We were confident when we arrived at the marina that everything would go as planned. And it did. We were greeted at the hotel, driven to the marina …

YACHT CHARTERS

Matthew Gunnison

“Thanks for helping to coordinate!”

It was terrific, thanks. Sail Marine is a great outfit. Thanks for helping to coordinate! Best, Matt

Gary Ziegler

“A mega thank you for your excellent service!”

A search on the internet produced the 12 Knots operation. With apparent quality staff and experience along with the best price on a bareboat monohull influenced me to book a boat with them. We were not disappointed. Correspondence was timely, courteo…

United States

“My first experience with 12 Knots”

My first experience with 12 Knots, very good services, very good communication skills, prompt reaction and easy procedure for booking. I highly recommend their services. Clearly, not everybody could be satisfied, but personally I did not find any wea…

Flori Grottoli

“Spanish Virgin Islands are stunning / March 2019 / Puerto Rico / Dufour 412”

The experience was beautiful and the Spanish Virgin Islands are stunning! Even though we started off with a few setbacks (had to switch boats because of technical issues), the marina made good and was very accommodating....they did the very best they…

Oscar Serra

“We tried to make the most of it, but it was far from ideal”

Hey Grigory, thanks for asking. The boat was not in good condition. For example, there were no mooring, deck or motoring lights, so we feared a boat would hit us while we slept, and were not complying with the law while sailing at night. The anchor w…

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Sailing Around Windward and Leeward Islands of the Caribbean

The  Caribbean covers a huge region of widely spread islands 2,000 miles (3,218 km) long.

The larger ones have become sovereign countries with broad range of amenities for sailors, while the smaller ones still preserve its untouched rural charm and tranquility.

From the western tip of Cuba to the Leewards in the east, then south to the top of South America and along Venezuela’s north coast – this chain of islands has created a hook-like shape around the Caribbean Sea. Location like this is always an enticing bait for sailing - perfect climate and  array of diverse cultures, customs, cuisines and experiences, water sports and an unlimited number of other attractions.

Planning sailing vacations in Caribbean, you may wish to consider these groupings of the islands as points of your itinerary, as they contain many popular cruising areas and harbor stops. There is no doubt that in the scope of Caribbean bareboat or skippered yacht charters  both groups have their charms and countless reasons to explore, which definitely makes it a great sailing destination.

Caribbean yacht rentals

12 Knots offers eleven yacht charter bases in the Caribbean region, each with unique individual character, providing sailing experience for everyone, from a novice to an experienced sailor. This region comprises more than 700 hundred islands and islets, so you can choose Caribbean sailing vacations with shot and easy hops or more challenging passages.

Taking Caribbean sailing vacations, you will find warm and steady trade winds in picturesque surroundings; discover plenty of great bars and authentic cuisine!

It’s up to you, choosing between the Leeward Caribbean islands with short and easy hops with line-of-sight sailing and the Windward with more challenging open water passages. Wherever you go, you will return home relaxed, refreshed and ready to start planning your next Caribbean sailing adventure.

The Windward islands

Windward Islands located at the southern end of the Caribbean island chain and stretch for over 300 miles to the south-eastern end of the Caribbean Sea. The Windward Islands are simply called so due to their position as they are exposed to the northeast trade winds. For experienced sailors, it can be right choice to sail among the four main islands: Martinique, St. Lucia, St. Vincent and Grenada. They lay far apart each other allowing open ocean sailing and while steady easterly trade winds, make passages north or south easy. With constant 12 to 25 knots wind, Caribbean sailing is among best in the world. Night anchorages in peaceful and protected areas give sailors freedom to explore and soak up British and French island culture. The islands of St. Lucia, St. Vincent and Grenada  were British colonies until they gained independence during the 1970s. Martinique is still an overseas department of France.

The climate of the Windward Islands is definitely a marine one.

When tropical heat reaches its peak, steady trade winds and daily sea breezes come to rescue.

Typically, dry and wet seasons go hand in hand here. Although the priority of more rainfalls is given to the eastern side of the islands mainly due to the prevailing north-east trade winds there.

The islands east of Puerto Rico were called “Windward Islands” by the Spanish, while the islands south of Puerto Rico were named as “Leewards “. And Dominica positions itself right on the border line between the Windward and the Leeward Islands.

Long time ago some of the islands used to be French colonies, subsequently gained its name as The French Antilles.

The population of the Windward Islands is mostly of African origin, with some exceptions of Chinese and Caucasians. The present day Windward Islands will welcome tourists with upscale resorts, stunning beaches and pleasant sunny weather.

After cruising through the Windward Islands, you may wish to set sails to the Leeward Islands.

The Leeward islands

The Leeward islands are located on the eastern edge of the Caribbean Sea and form the northeastern boundary between Caribbean and Atlantic Ocean, extending from Puerto Rico to the Windward Islands, forming part of the Lesser Antilles chain.

Although 700 miles long stretch of these magnificent isles mostly constitute the whole body of the Leewards, it provides the abundance of enjoyment: quaint fishing spots, ancient ruins and delicious authentic cuisine.

Blessed with balmy temperatures all around the year, The Leeward Islands are called leeward because they're away from the wind or downwind (in the "lee"). Leeward group of Caribbean islands includes: the U.S. Virgin Islands, the British Virgin Islands, Anguilla, Saint Martin, Saint-Barthelemy, Saba, Sint Eustatius, Saint Kitts, Nevis, Barbuda, Antiqua, Redonda, Montserrat and Guadeloupe.

One of two "sister islands", St Kitts and Nevis, provides a brilliant Caribbean experience, from their picture-perfect beaches and volcanic mountains to friendly locals and layers of history to explore. For the water sport lovers, there are numerous aquatic activities that include fishing, diving, windsurfing and surfing.

St.Kitts and Nevis

Switch from sailing to inland for a change and St.Kitts and Nevis will deliver the most exceptional hiking in the Caribbean. The dormant volcano of Mount Liamuiga is considered to be the toughest to climb. And with the experienced guide you may even try to descend in its crater!

The unspoiled landscape of dry littoral forest and rainforest will present memorable show of fauna and flora. Many plants are of culinary and medical use, and some even used in black magic, as informative guides would point out its botanical value.

The wild life-lovers will not be disappointed with variety of different types of exotic animals.

Actually, the Great Salt Pond has become famous for its largest habitat of green velvet monkeys.

St. Kitts and Nevis will keep you captivated with majestic view of huge conical shells, remains of old sugar mills, along with some other plantation ruins, built in the 18 th century.

Back to water activities, and tourists will be pleased with what these two island can offer: deep-water fishing, snorkeling, scuba diving and more.

Then in order to satisfy your growing appetite visit two popular restaurants: Carambola and the Shipwreck Bar and Grill to enjoy its delicious local meals.

A yacht charter in the Caribbean Leeward Islands offers sailors an unrivalled remarkable experience. Enjoy tropical landscapes, pristine palm-lined beaches and azure waters — all the joys of marine life.

Sailing over the Leeward Islands may have all the pleasures to offer: the Tropical rainforests, glittering coral reefs, and luxury sand beaches. That’s probably why most of the known tourist resorts on these islands play a critical role in their economy, as do banking and fishing. Many of them also rely on their status as a tax haven to promote offshore financial services as a source of government revenue. But there is much more to discover in the Leeward Islands. These Caribbean islands provide great variety of yachts for charter and pleasant sailing vacations. Most of the Leeward Islands are located close to each other with moderate winds from 10 to 15 knots and rather low wavers. BVI is the most popular area for Caribbean charters either bareboat or luxury crewed vacations. This is the right place for the novice sailor’s easy passages in line-of-sight sailing.

The climate of the Caribbean Leeward Islands can be described as tropical, but much drier than in Windward Islands. Though the climate does vary from island to island and can even be different in different parts of the same island. Rainfall increases with elevation and in more southerly latitudes. In some cases trade winds look like refreshing tonic to the tropical heat. There is minor seasonal variation, although the second half of the year, the wet season, is slightly warmer and rainier. The best time for sailing in the Caribbean may be the first half of the year. At this time the temperatures usually range between 81°F (27°C) and 95°F(35°C). Annual rainfall averages about 40 to 50 inches (1016 to 1270 mm). Keep in mind, that nearly every island had been severely damaged by hurricane activity in its recent history.

English is the most widespread language all around the islands, plus many of the people speak French and Dutch on the St Martin Island. Both English-based and French-based Creole are also spoken. The prevailing currency is The East Caribbean dollar. But St Martin is odd man out again, circulating the Netherlands Antilles guilder in the Dutch area and the Euro in the French region. Nevertheless, the US dollar is widely accepted throughout the islands.

If you eager to take part in sporting activities, then you may be pleased to know that cricket is widely played and followed in the former British territories. Besides, as in the rest of the Caribbean, music is also always a big part of local life. Enjoy the magical sounds of calypso, soca, steelpan, reggae, salsa and jazz — all of the mentioned has their adherents.

During your Caribbean yacht charter, you may wish to participate in some major holiday celebrations, including the St Kitts Christmas, New Year carnaval, the annual music festival, as well as Anguilla’s Emancipation Day and Culturama festival on August 1st.

The culture of the Leeward Islands is varied by different influences, including French, Dutch and West Indian. Due to that sailing around the Leeward Islands provides a wonderful choice of cuisine and some great restaurants to satisfy your affection for the finest dishes. By the way, the island of Anguilla offers true gastronomic feasts. When sailing in the Caribbean Leeward Islands, be sure to try freshly caught lobsters with a glass of wine.

Sailing the Caribbean With 12 Knots

So, while planning a Caribbean charter it is highly recommended to decide on how many islands you would like to visit in a given time frame. Research Caribbean boat rentals and determine which island you would like to have as a starting base. Then you can plan an itinerary for the week or ten days, taking into consideration distances between the islands and activities you would like to have, like island tracking, scuba diving, snorkeling, volcano hiking, or even shopping.

12 Knots team will give you plenty of useful information not only on the bareboat charter in Caribbean, but also itineraries, places of interest and peculiarities of each island.

Taking a yacht charter in the Caribbean is just a perfect combination of sailing and relaxation, authentic culture and a range of water sport activities. In a few words, this area may always offer something for everyone in these amazing islands’ surrounding.

Frequently Asked Questions about yachting in Caribbean

How much does it cost to rent a yacht in caribbean , how many boats are available for rent in caribbean , what are the main yacht charter bases in caribbean , what boats are available for charter in caribbean .

Book an unforgettable crewed yacht charter vacation.

View available yachts:.

Book with the Caribbean specialists. For over 19 years we have been a leading yacht charter brokerage connecting groups like yours with the best crewed yachts available for charter in the Caribbean including the Virgin Islands / BVIs / USVIs, Leewards, Grenadines and Bahamas.

Utilize out firsthand knowledge about available charter yachts, crews and locations to book the best yacht and crew for your budget and travel style.

Start planning your vacation today!

Sail away to white sand beaches, consistent Caribbean trade winds, clear blue water, sheltered island bays great for cruising, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

Power Yachts

Specials and last minute discounts:.

These crewed catamaran charter specials are available for new reservations sailing from St Thomas or Tortola in the Virgin Islands, or elsewhere in the Caribbean. Contact us now for further information and a no-obligation quote.

See all of the current crewed yacht charter specials and discounts.

Our customers say it best. Check out their feedback.

The crew was wonderful. Kayla and Chris fit in with our family perfectly and made us feel comfortable and at home aboard Felix. Their humor and knowledge were both greatly appreciated!

The food was fantastic; Chris truly spoiled us! I personally have a challenging diet with several allergies and he made sure every meal felt complete vs feeling like an “allergy friendly” meal. And it was all delicious!

The yacht was very comfortable and clean. It had all of the accommodations we needed - nothing was missing... I enjoyed the various different viewpoints to sit or lounge at while we went from island to island.

Kress S, aboard Catamaran Felix , November 2023  sailing the Virgin Islands

Melody D, aboard Catamaran Excess , January 2023  sailing the British Virgin Islands

Mathieu C, aboard Catamaran Cashmere , December 2022  sailing the Caribbean Leeward Islands

> See all of our crewed yacht charter reviews

Caribbean Yacht Charter Vacations

A crewed Caribbean yacht charter offers you the freedom to explore this tropical paradise without limits and at your own pace.

With accommodation, a professional captain, a personal chef, all meals, cocktails, wine, beer, snacks, fuel, equipment, and water toys included, few other vacations offer such an extraordinary experience and value.

Itineraries are completely flexible within your cruising area. Sail the diverse US and British Virgin Islands, the undeveloped and resort islands of the Caribbean Grenadines, or charter a luxury power yacht to cruise St. Martin, St. Barts, and Antigua in the Caribbean Leeward Islands.

Sailing Direction's charter brokers help you book a private crewed yacht in the Caribbean for any group size and budget. Whether you're looking for a family sailing vacation, a couple's adventure holiday, a BVI yacht charter, or a honeymoon or anniversary celebration - we've got you covered for an unforgettable crewed yacht charter experience.

• Sailboat rental in the Caribbean
• Boat rental
• Sailboat rental

Sailboat BENETEAU OCEANIS 48 14.63m 80hp  (2018)

Sailboat BENETEAU OCEANIS 41.1 12.43m 45hp  (2018)

Sailboat Bénéteau Oceanis 41.1 12.00m 45hp  (2018)

From $269 per day.

Sailboat Moorings 46.3 14.60m 57hp  (2019)

From $468 per day.

From $534 per day

From $568 per day

Sailboat Sunsail 51 15.38m 75hp  (2018)

From $891 per day.

Sailboat Sunsail 410 12.35m 40hp  (2019)

From $334 per day.

From $340 per day

Sailboat JEANNEAU Sun Odyssey 349 - ZAURAK 10.34m 21hp  (2018)

From $649 per day.

Sailboat Moorings 382 11.50m 29hp  (2018)

From $390 per day.

Sailboat Bénéteau Oceanis 54 - 3 + 1 cab. 17.12m 110hp  (2024)

From $681 per day.

Sailboat Beneteau First 40.7 12m  (2008)

From $371 per day.

Sailboat Moorings 42.1 12.43m 45hp  (2019)

From $440 per day.

Sailboat Beneteau Oceanis 48 14.00m 80hp  (2017)

From $1,153 per day.

Harmony 52 Sao Jorge  (2007)

From $829 per day, explore the caribbean by sailboat.

There’s no better way to experience the Caribbean than by sailboat. With over 7,000 islands and islets, the Caribbean is a sailor’s paradise. The warm, turquoise waters and constant trade winds make it the perfect sailing destination. It's no wonder why so many people choose to rent a sailboat to island hop and explore this beautiful part of the world!

The Caribbean islands are home to some of the most stunning sailing destinations in the world. From the British Virgin Islands to Grenada , there’s a destination for every type of sailor. The white sand beaches and crystal-clear waters are breathtaking, and the lush tropical landscapes are simply unforgettable. Whether you’re looking for a romantic getaway, a family vacation, or a sailing adventure with friends, the Caribbean has it all.

Chartering a sailboat in the Caribbean is easy with Click&Boat. We offer a wide variety of sailboats to choose from. Our charter fleet includes boats of all sizes, so whether you’re traveling solo or with a large group, we’ve got you covered. Connect with local Caribbean sailboat owners to create your dream sailing experience.

With Click&Boat, you can find the perfect boat for your needs and budget. Use our price filter when searching for your sailboat rental in the Caribbean to find one that fits within your budget. Don't miss out on the opportunity to explore the Caribbean by sailboat!

Why should I rent a sailboat in the Caribbean?

There are many reasons why renting a sailboat in the Caribbean is the perfect way to explore this beautiful part of the world. First and foremost, sailing is the best way to experience the Caribbean's natural beauty. With so many islands and islets to explore, there's always something new and exciting to discover. Whether you're looking for a secluded beach, a hidden cove, or a lively port town, a sailboat gives you the freedom to explore at your own pace.

Sailing in the Caribbean is also an incredible adventure. The constant trade winds make perfect sailing conditions, and the warm, clear waters are perfect for swimming, snorkeling, and diving. With so many islands to choose from, you can plan your perfect sailing itinerary, and experience a different island and culture every day.

Click&Boat has ideal sailboat options for you, no matter if you’re an experienced sailor or a novice with the option to rent with or without a captain. Whether it’s your first time stepping on a sailboat or if you are an expert sailor, you can find a boat that suits your needs.

How much does it cost?

The cost of renting a sailboat in the Caribbean varies depending on several factors, including the location, the length of rental, the size and make of the sailboat and more. Generally, the cost of renting a sailboat for a day in the Caribbean can range from $300 to $800, depending on the boat's size, features, and location. For a week-long rental, the cost can range from $2,800 to $4,200, on average.

It's important to note that the cost of renting a sailboat in the Caribbean can vary significantly depending on the time of year you plan to sail. During peak season (typically November through April), prices tend to be higher, while off-season rentals can be more affordable. Additionally, some locations, such as the British Virgin Islands, may have higher rental prices due to their popularity and limited availability.

When renting a sailboat in the Caribbean, there may be additional costs, such as captain and mooring fees. However, despite these additional costs, renting a sailboat in the Caribbean can still be a one-of-a-kind way to experience this beautiful part of the world.

When is the best time to go?

Sailing in the Caribbean is possible year-round, but the best time to go depends on your preferences and priorities. If you're looking for calm waters and consistent weather, the best time to go is during the high season, which runs from December to April. During this time, you can expect dry weather, calm winds, and clear waters, making it the perfect time for island hopping and exploring the region's stunning beaches.

However, if you're looking for a more affordable and less crowded sailing experience, the shoulder season (May to November) might be a better option. While you might encounter more rain and occasional tropical storms during this time, you'll also enjoy lower prices on yacht charters and have more anchorages and beaches to yourself.

The harbors in the Caribbean

The Caribbean is known for its stunning beaches, balmy weather, and vibrant culture. But it's also a great place to go sailing and explore the many islands of this beautiful region. If you're looking for a sailboat charter in the Caribbean, there are plenty of options to choose from.

Here is a list of different harbors and marinas where you can dock your boat and enjoy exploring the Caribbean:

• Simpson Bay Yacht Club & Marina: This marina on the Dutch side of St. Martin is a great starting point for exploring the beautiful waters of the Caribbean.
• Rodney Bay Marina: Located in St. Lucia, this marina is a popular destination for sailors, offering easy access to nearby attractions and beautiful anchorages.
• Antigua Yacht Club: This historic yacht club in Antigua is a must-visit for sailors, with a beautiful clubhouse and world-class facilities.
• Soper’s Hole Marina: This marina in Tortola is a popular destination for sailors in the British Virgin Islands, with its lively atmosphere, restaurants, and easy access to nearby beaches and anchorages.
• Blue Lagoon Marina: Situated in St. Vincent in the Grenadines, this marina is a popular destination for sailors, with its beautiful scenery, nearby beaches, and access to stunning sailing destinations like Bequia and Mustique.

What are the best places to sail to in the Caribbean?

The Caribbean is home to some of the most beautiful sailing destinations in the world, with a wide variety of islands and destinations to explore. Whether you're looking for secluded beaches, lively towns, or stunning natural beauty, there's something for everyone in the Caribbean. Here are some of the best places to sail to in the Caribbean:

• Antigua : Known for its 365 beaches, Antigua is a popular destination for sailors looking to explore its turquoise waters and charming towns.
• St. Lucia : This lush island boasts stunning natural beauty, from its iconic Pitons to its black sand beaches and rainforest.
• Tobago Cays: This group of small, uninhabited islands in the Grenadines and St. Vincent is a true paradise, with crystal-clear waters and plenty of opportunities for snorkeling and diving.
• British Virgin Islands: A sailor's dream destination, the BVI offers everything from secluded anchorages to bustling beach bars and restaurants.
• Grenadines: This chain of islands is known for its pristine beaches, crystal-clear waters, and laid-back vibe, making it a perfect destination for a relaxing sailing vacation.

Other great destinations to explore in the Caribbean include the Bahamas, St. Martin, the Dominican Republic, and many more. No matter where you choose to sail in the Caribbean, you're sure to have a memorable experience.

Renting a sailboat with or without a captain

Another great reason to charter a sailboat in the Caribbean is the availability of skippers. If you're new to sailing, a captain can make all the difference. They'll know the best spots to go and which tides to avoid, so you can focus on enjoying yourself. Plus, they'll handle all the logistics so you can just enjoy the sailing.

But if you're an experienced sailor and are looking to take full control of your vacation and enjoy the open sea, you should consider going on a bareboat charter! Before setting sail make sure you have the right documents.

What brands or models can I rent?

Whether you choose to charter with a private or professional owner, a sailboat rental in the Caribbean has never been so easy. With Click&Boat, the world’s leading boat rental service, book the boat of your dreams whether it be a bareboat charter or a crewed yacht!

Rely on the best prices, an internal messaging tool for owners and renters, as well as a knowledgeable team of advisors ready to help- because booking shouldn’t be a hassle.

Choose to set sail with your favorite shipyard Jeanneau, Beneteau, or DuFour, and discover the islands of the Caribbean, in comfort and style.

Horizon Yacht Charters

British Virgin Islands

St Vincent & The Grenadines

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US Virgin Islands

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Recent news.

• Spirit Airlines Has More New Nonstop Flights to San Juan, Puerto Rico
• American Airlines Is Adding More Daily Flights to St Thomas, USVI
• Avelo Airlines Just Kicked Off Two New Nonstop Routes to Puerto Rico
• United Just Launched New Daily Nonstop Flights to Puerto Rico
• Avelo Is Launching More Nonstop Flights to Puerto Rico
• Delta Is Adding More Flights to St Thomas
• American Airlines is adding more flights to the British Virgin Islands
• Air Canada Adding More Flights to St Vincent

Sailboat & Yacht Charter in the Caribbean: The Best Companies

One of the world’s most desirable yachting destinations, the Caribbean captivates all who visit with its heady mix of natural beauty, calm waters and world class tourist amenities. For private yacht charter guests, the Caribbean is particularly well set up, with a vast number of charter companies offering yacht rental packages in the region.

Yachts anchored out in Salt Whistle Bay in the Grenadines (Photo: _dChris via Flickr / CC BY 2.0)

Whether you’re seeking a crewed yacht or a bareboat charter, a sailboat or a motorboat, there’s a huge choice of yachts available in the Caribbean. We’ve picked out 3 of the best companies currently operating that we’d recommend for Caribbean yacht charters.

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Home » Destinations » Boat rental » Sailboat charter » Caribbean

Sailing in the Caribbean is a dream of many sailors. The beautiful sea, the trade wind and the pleasant waters are ideal for a sailing vacation, not to mention the fact that navigating amongst the many islands here is quite exciting. The ports and islands in the Caribbean are ideal for those who love adventures, beautiful sights, and hotness.

Read more information about sailboat charter in the Caribbean on the following tabs: About Caribbean , Caribbean weather . Get some inspiration from the Caribbean itineraries tab and start planning your next sailing itinerary, read detailed descriptions of Caribbean sailing destinations , or Caribbean sailing articles.

The most popular Caribbean sailboat charter destinations

About caribbean, caribbean weather, caribbean itineraries.

Antigua sailboat charter

Bahamas sailboat charter

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Sailboat charter Guadeloupe

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Sailboat charter Mexico

Sailboat charter USVI

Location of the Caribbean

The phrase, Caribbean region, stands for the North and Central American groups of islands. In a broader sense, some Central and South American countries also belong here, such as Columbia or Venezuela. There are more than 700 islands in the region. We can divide the Caribbean Islands into three main parts. The Bahamas, the Greater Antilles, and the Lesser Antilles.

Beaches in the Caribbean

There are several gorgeous beaches, gulfs, and lagoons here. The crystal clear seawater and warm sunlight create a picturesque view. The beauty of the landscape will surely make your travel memorable. The white sandy shores of the Caribbean Sea are among the most astonishing swimming sites in the world. Here are some:

Gulf of Maundays, Anguilla

One of the most popular holiday resorts, Cap Julica is in this gulf. The amazing five-star resort provides full comfort and luxury. Thus, no wonder celebrities also like staying here. The beach has a private bar and other services as well.

Valley Church, Antigua

A cosy beach that enchants visitors with different shades of blue water. The water is calm and crystal clear, white sand carpet covers its shore. You can discover hundreds of other beaches between Antigua and Barbuda. They will certainly outshine your expectations. The secret gems of this area are its hidden gulfs, which you too can explore if you rent a boat.

Pink Sands beach

Many visit Harbour Island to view this famous section of the seaside. The coral is a unique mixture of broken shells, miniature stones, and calcium carbonate. It colours the sand with pink fragments. It’s a wide and long beach surrounded by calm water. It can be an ideal and beautiful venue for wedding ceremonies, sports, or yoga.

Treasure Beach, Bahamas

It’s among the best beaches in the world. Treasure beach is a 3, 5- mile -long section of the shore with every service available to make a vacation incomparable and even more excellent. You can enjoy pleasant cafés and restaurants or try watersports.

Main attractions in the Caribbean

The picturesque scenery welcomes visitors with several colourful and unique programs. Besides beautiful beaches, you can take pleasure in viewing the exotic flora of the jungle or the underwater wildlife. Sea turtles are amazing residents of the Caribbean Sea. They are one of the endangered species, thus, numerous rescue and breeding programs started in the past few years to protect the animals. Many visitors come to Puerto Rico to see the turtles, while they’re laying their eggs in the sand. They also come to see the exciting moment, when the little turtles leave their nests and go into the water. Besides water and seaside sights the Caribbean region also has a rich cultural heritage. There are more than 40 museums in Cuba, that display art, music, the revolution, chocolate, or cigars.

The Caribbean weather

The Caribbean region has the traits of all year hot and humid tropical climate. The weather is somewhat cool and dry from the middle of January to the middle of April. From the middle of June to the middle of November it’s usually hot, wet, and rainy. Subtropical monsoon climate dominates in the region. The average yearly temperature is 28 °C.

Sailboat charter in the Caribbean

A roundtrip on the Caribbean Sea could be a very exciting and memorable program for the whole family. Rent a small boat, a luxury yacht, or a sailboat. It’s important that you find out about landing places. The Caribbean region involves numerous ports, small and large. However, they might be very different. The most popular and high-standard ports are in the larger cities. These are the ports of for example Nassau, Falmouth, Puerto Rico, Philipsburg, or Mexico. They are well-equipped and provide all the services necessary for boating. The majority of sea centers and smaller islands are in daily connection.

The most popular ports in the Bahamas

Great guana cay.

Great Guana Cay is located in the centre of the Exumas. It has two great anchorages: Black Point and Little Bay. Black Point is a true gem with a nice port and several moorings. People are very friendly and casual, and they find it important to help sailors in any way they can. Little Bay is a small bay at the southern end of Black Point. The sea bottom is sandy, making it ideal for securing our boat safely. The depth of water is app. 3-4 metres. There is a beautiful beach here, but there are no establishments, ports or shops. Information about Exumas sailing or boat rental in Exumas

Spanish Wells

Spanish Wells is located on St. Georges Cay, west of the northern corner of Eleuthera. Its port is constituted by a long channel bordered by two small islands. It is protected well and is only open for the winds coming from the eastern direction. There is a great port and a hurricane hole in the west where boats are tied to mangrove trees. There are six anchoring buoys on the eastern side. We can find Spanish Wells Yacht Haven & Marina here which is a full-service yacht marina with 40 berths; besides the basic services, they also have a bicycle rental.

The downtown is within walking distance. We can anchor at Royal Island Harbour in the west, which provides ideal anchorages for vessels with a larger draft. The only disadvantage is that they have no amenities or services. Information about Eleuthera sailing , or boat rental in EleutheraMore about Bahamas sailing tours, or Bahamas yacht rental

The most popular ports in the BVI

Nanny Cay is located on the southern coast of Tortola. It is located a little over 3 kilometres from Burt Point. At this port, we have the opportunity to pull our boat from the water, among other services. Nanny Cay Marina offers 320 berths; 120 on the outer parts and 200 in the inside. They provide access to fuel and electricity in both areas. We need to pass through a narrow route for entry.

Road Harbour

Road Town is the capital of Tortola and the sailing centre of the British Virgin Islands. We can enter the port through the Sir Francis Drake Channel . Road Harbour has several yacht marinas providing full service and accommodation. We can find Road Reef Marina, Fort Burt and Wickham’s Cay I and II here; Road Reef Marina and Fort Burt are on the western side, while Wickham’s Cay is on the north. There are over 120 berths and downtown Road Town can be found nearby. Many sailors start their trip here when visiting the British Virgin Islands. Information about sailing in Tortola , or boat hire in Tortola

Virgin Gorda Yacht Harbor és St. Thomas Bay

The Virgin Gorda Yacht Harbor is in St. Thomas Bay. It is easy to approach it, we only have to sail the marked channel. The harbour is beautiful, offering great services and marine gas. There are 100 berths, and it is possible to stay for only a few hours, a day, or long-term as well. It is close to the centre of Spanish Town. It is a very peaceful town where you can find many shops, restaurants, and bars. One of the most famous attractions of the town, The Baths, is about 3 km from here. This is a collection of granite rocks on the beach that have become large rock formations. The rocks from tidal basins, channels, and spectacular caves open to the surrounding waters. Information about Virgin Gorda sailing , or Virgin Gorda boat chartersMore about BVI sailing routes , or BVI boat rental

The biggest ports in Puerto Rico

San juan cruise port.

With two terminals, San Cruise Port is one of the largest and busiest ports in the Caribbean. The two terminals can accommodate up to 9 cruise ships at the same time. Due to its geographical location, the port is safe even during hurricane season. The port offers several services like towing, drinking water access and electricity, telecommunication services and shops. The city’s tourist attractions are easily accessible by public transport.

Marina Puerto Chico ( Fajardo )

The marina of Fajardo is located on the east coast of Puerto Rico. It is a natural, quiet coast, and the depth of the water is 5-6 m. Despite its small size, it has a great infrastructure: water, electricity and refuelling are available. You can easily visit Culebra, Vieques and the British Virgin Islands from here.

Port of Mayagüez

The third busiest port in Puerto Rico is northwest of downtown Mayagüez, stretching for 6 km along the coast. The depth of the water is 8-9 m. Despite being one of the smaller ports, it can accommodate boats up to 150 m in length. The communication infrastructure is also outstanding. More about Puerto Rico sailing, or boat rental in Puerto Rico

The most popular ports in Mexico

La Paz is the most city in southern Mexico on the Baja California Península. It has several ports.. One of the best-equipped ports is Marina Cortez, located in the heart of the bay. It offers a number of exclusive services for even the largest sea yachts.

The city’s port, called El Cid, is way more than a simple landing opportunity. There is a bustling market and several miles of nearby beaches with golden sand. The local dive shop is excellent, you can get all the necessary equipment here. In the port area, you will find plenty of high-quality accommodation opportunities. More about Mexico sailing , or boat rental in Mexico

The biggest ports in Cuba

Port of cienfuegos.

The main port in the southern part of the island is La Perla del Sur or the Pearl of the South. The port of Cienfuegos is considered a large port in Cuba. It can accommodate boats up to 150 m. The depth of the seabed is 12 m. While Christopher Columbus visited in 1494, it was formally founded in 1819.

Port of Santiago de Cuba

The second-largest port city of Cuba is located in the southeastern part of the island, in Oriente Province. It is a major port for import and export in the region. The bay is quiet and protected against winds. The famous Casa del Habano is a few-minute walk from the port. Here, you can buy the best-quality Cuban cigars and you can visit the Bacardi Museum. More about Cuba sailing, or boat rental in Cuba . Another option is to explore the sea by yourself on the deck of a yacht charter. If your only wish is an amazing sea vacation, or the presence of stunning natural wonders, visit the Caribbean Sea to find all of these.Find sailing routes in the Caribbean .

More information about the Caribbean

Caribbean sailing routes & Caribbean sailing destinations Sailing destinations & Sailing routes

Sailing in the Caribbean: an unforgettable experience for you. Caribbean sailing trips

Sailing in the Caribbean is a dream of many sailors. The beautiful sea, the trade [...]

For more precise information about the Caribbean area,  please narrow down your search. It is necessary in this case, because of geographic diversity and the large scope of the area. First select a destination on the sailboat charter in the Caribbean tab and choose the Weather tab of the selected area and read the related description.

Rent a sailboat in the Caribbean, and cruise around the Caribbean

Puerto rico sailing itineraries.

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Caribbean Splurge: A Sailboat of Your Own (Well, Sort of)

What you need to know to charter a sailboat in the Caribbean, from costs and type of vessel to timing and itinerary.

By Christopher Hall

Last April, Chris Kotchick, a Scranton, Pa., oral surgeon, and his family spent a week on a chartered catamaran in the calm, clear waters off the British Virgin Islands. A crew of two — part of the deal — ran the show.

Until then, Dr. Kotchick said, the sum total of his nautical experience had been riding ferries. But his search for a vacation that would appeal to his wife, Bridget, a high school biology teacher, and their two teenage children led him to a 50-foot-long boat, which they used as a base for swimming, snorkeling, wake-boarding and scuba diving as they sailed from island to island. They slept onboard and mostly skipped onshore restaurants, wowed by the crew-cooked meals that could be shared with their daughter, who has celiac disease.

As to cost, the trip was, for them, an affordable splurge — just over $20,000. “It wasn’t that much more than the blowout Disney World vacation we took when the kids were younger,” said Dr. Kotchick, adding that two others had joined the family on that trip. “And it was a lot more fun.”

Though the image of yachting in the Caribbean skews more oligarch than average Joe, the Kotchicks are far closer to typical crewed yacht clients than the likes of Jeff Bezos aboard his schooner, which is more than 400 feet long and cost a reported $500 million. After a pandemic lull, more people of comfortable, but not necessarily extraordinary, means are booking these trips, and the trend is edging higher. According to an April 2023 report from Fortune Business Insights, the global charter yacht market — including both crewed and sail-it-yourself, or bareboat, charters — is expected to grow 5.5 percent by 2030, with yachts under 40 meters (about 131 feet) accounting for the largest share.

Because the cost includes a crew, passengers don’t need specialized maritime knowledge, which means the trips draw a variety of travelers.

“Some of our clients are more into active sports, and others prefer relaxing with a book or checking out onshore restaurants, bars and resorts,” said Carlos Andrade, a captain who, with his wife, first mate and chef, Maribel Ramirez, has run trips in the Caribbean and elsewhere for more than 30 years, most recently aboard their 44-foot catamaran, Alizé . “But all of them love the outdoors and simply being close to water.”

For Steve McCrea, a broker at the yacht charter agency Ed Hamilton & Co. , the most common question from prospective clients is whether their kids will get bored on a boat. “I tell them that, yes, it’s a sailing vacation,” said Mr. McCrea, who has been booking crewed Caribbean trips for 26 years, “but, in fact, it’s more like a floating resort on the move, with loads of activities, sports gear and great beaches where you can spend the day.”

Jim Grant, a broker at Carefree Yacht Charters , said passengers do not need to meet any specific benchmark of health or physical fitness. “If you can comfortably navigate jet travel to get to the boat,” said Mr. Grant, “you’ll be fine on board.”

The nitty-gritty: boats and cost

In the Caribbean, crewed catamaran sailboats with their double hulls far outpace power boats and single-hull sailboats as the vessel of choice. “They’re more stable on the water, which is great for people without a lot of sailing experience,” said Mr. Andrade, the yacht skipper. “And in terms of onboard space, they can’t be beat when you compare different kinds of boats of similar length.”

A boat’s size and age largely determine the cost of a charter, with price bumps occurring during the holidays. For a weeklong trip for six passengers aboard an older catamaran with three en-suite guest cabins and a crew of two in its own cabin, the per-person fee starts around $2,500 for a vessel under 50 feet. That gradually rises to $5,000 and up for a somewhat larger and newer boat and zooms ever higher as size and newness increase. A week aboard a two-year-old, 80-foot catamaran with four en-suite cabins and a crew of four, for example, can easily approach $20,000 per person. In the Caribbean, the charter fee is usually inclusive, meaning that meals, alcohol and fuel are folded into the cost. Only the customary 15 to 20 percent gratuity is extra.

Crewed charter trips can fill up fast. “For the best selection, you should think about booking at least six months in advance for popular times like spring break, Easter and Thanksgiving,” said Els Kraakman, a British Virgin Islands-based broker with Waypoints Yacht Charters . “For Christmas and New Years, it can be more like a year.”

Unless you’re chartering a megayacht with its own gym and sauna, amenities are fairly uniform. Even on moderately sized vessels, they usually include Wi-Fi, air-conditioning, music systems, swimming platforms, on-deck showers (in addition to those in cabin heads), motorized dinghies for water sports and transport to shore, and an arsenal of sporting equipment like kayaks, stand-up paddle boards, and gear for snorkeling and fishing.

Alfresco, onboard dining is a big selling point, with galleys on many boats staffed by cooks with professional experience.

“The meals were fabulous,” said Steve Tyler, a retired process safety engineer from Kansas City, Mo., who recalled an especially memorable chicken-coconut-cream curry served on the 51-foot catamaran in the British Virgin Islands that he chartered earlier this year with his wife, Laura, and their 19-year-old and 23-year-old daughters. “Our daughters are so busy with their own lives,” said Ms. Tyler, a retired editor. “It was wonderful for all of us to share three meals a day.”

Using a broker

Brokers arrange most crewed charter trips in the Caribbean, especially for first-time passengers, with the standard 15 percent broker’s fee being paid by the boat owner. Brokers can book virtually any yacht with a crew. The best of them, however, tend to work exclusively with charters run either by boat owners themselves or a team dedicated full-time to the boat — what some call true charters — as opposed to bareboat operations with a freelance captain and cook hired for a single trip.

Many websites appear to offer brokerage services, but actually function more as booking sites. “Real brokers talk with clients before booking to get a sense of who they are and what their expectations are for the trip,” said Mr. Grant. “Based on those conversations, they recommend boats and crews they actually know about from prior bookings, personal connections or visits to the annual charter yacht shows.” Many top brokers are members of professional associations like the Charter Yacht Brokers Association or the American Yacht Charter Association .

Matching crew to client is particularly important. In addition to running the boat and cooking meals, crew members act as hosts, concierges and de facto tour guides, and they can be in close quarters with clients, especially on smaller boats.

So, where are you sailing to?

When you consider that there are roughly 7,000 islands in the Caribbean region, choosing one or several for a crewed charter might seem daunting. But the Caribbean’s charter fleet is concentrated in only a handful of locales with the right combination of good sailing and onshore services. Itineraries tend to be similar no matter how big your boat is. In fact, smaller vessels often have an advantage in being able to travel and overnight in shallower, close-in waters that are off-limits to mega yachts.

In the Bahamas, a popular destination that technically lies in the Atlantic Ocean, boats (including power yachts) make trips from Nassau into the Exumas, a chain of 300-plus low islands and cays with few inhabitants and miles of beaches. The U.S. Virgin Islands, with National Park Service sites and other onshore attractions, boasts a significant charter fleet. In the Leeward Islands, Antigua and St. Martin appeal to those looking for serious ocean sailing and, in the case of St. Martin, especially the French side, good food. South of normal hurricane routes, St. Vincent and the Grenadines, a group of 32 cays and small, agricultural islands, sees an influx of charter boats during what is peak hurricane season for many other Caribbean islands.

The top destination by far, however, is the British Virgin Islands, 50-plus diverse islands — some sparsely inhabited, others dotted with resorts and well-known watering holes — whose terrain ranges from green mountains to sugar-sand beaches.

On their separate trips, the Tylers and Kotchicks each hopped around islands like Tortola, Jost Van Dyke and Virgin Gorda, and made the longer sail to more remote Anegada, home to vibrant pink flamingos.

For the Tylers, the British Virgin Islands trip, which ran about $20,000, was likely a once-in-a-lifetime vacation. “It was expensive,” said Laura Tyler, “but definitely worth it in terms of the memories we created.”

The Kotchicks, however, aren’t ruling out another crewed charter. “I’d do it again in a heartbeat,” said Dr. Kotchick. “The only question is where.”

Follow New York Times Travel on Instagram and sign up for our weekly Travel Dispatch newsletter to get expert tips on traveling smarter and inspiration for your next vacation. Dreaming up a future getaway or just armchair traveling? Check out our 52 Places to Go in 2023 .

An earlier version of this article misstated Laura Tyler’s professional background. She is a retired editor, not a family law attorney.

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Where to Go This Winter

Whether you enjoy snowy landscapes or warmer weather, make the most of the season with the destinations below..

Embrace the Cold

Skiing Without Going Broke: Some states and resorts offer discounted passes for children and teens, knowing that those who start young tend to keep coming back .

Try Extreme Sledding : Looking for a thrill? Sledders in Switzerland are rocketing down steep, miles-long slopes , sometimes at night.

Spend 36 Hours in Vienna: The Austrian capital beckons as a wintry escape  with ice skating paths, cozy coffeehouses and a Christmas market in a palace.

Go Hut-to-Hut in Colorado: Challenge yourself with a backcountry adventure  that rewards skiers with soul-stirring scenery.

Stay in a Cozy Inn: Discover six hotels that are perfect for a weekend of sipping hot cocoa by the fire .

Escape to Warmer Weather

Learn to Love Waikiki:  It’s fashionable to dismiss the famous Honolulu beach as touristy and inauthentic, but it offers more if you know where to look .

Choose Your Cruise: Here are eight cruises to sunny spots  that offer respite from the winter blahs.

Unwind in the Desert: Spend 36 hours dining under the stars and riding mustangs  over a weekend at Joshua Tree in California.

Hunt for a ‘Perfect Beach’:  Search the coast of northern Puerto Rico for a superb stretch of golden sand .

Splurge on a Sailboat Adventure: What you need to know to charter a sailboat in the Caribbean , from costs and type of vessel to timing and itinerary.

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What To Know About Missing US Couple Sailing Caribbean

• By Brinley Hineman
• March 1, 2024

Caribbean authorities on Monday announced that an American couple sailing the Caribbean on their 48-foot St. Francis catamaran, Simplicity, were presumed dead after police say their boat was hijacked by escaped prisoners from Grenada. 

Royal St. Vincent and the Grenadines Police Force spokesman Junior Simmons said during a news conference that Ralph Hendry and Kathy Brandel are presumed dead after the couple’s disappearance. Simmons said authorities believe the couple was aboard their boat Simplicity when it was hijacked by three men accused of escaping police custody the day before. Their bodies haven’t been recovered as of Thursday afternoon.

The couple, experienced sailors, were on their final voyage with the Salty Dawg Sailing Association when it “took an unthinkable turn as Simplicity was found abandoned in St. Vincent, bearing chilling evidence of a violent struggle,” said a GoFundMe created for the couple’s family. 

Men accused of hijacking boat after escaping custody 

Grenada’s Police Commissioner Don McKenzie said Monday during a news conference that Trevon Robertson, 19, Abita Stanislaus, 25, and Ron Mitchell, 30, escaped custody at South St. George Police Station on Feb. 18. 

The escapees are accused of hijacking the Simplicity on Feb. 19. The boat was moored at Grand Anse, which is near the police station. While traveling to St. Vincent and the Grenadines from Grenada, “they disposed of the occupants,” police said. The men haven’t been charged in the couple’s disappearance. 

The men were later captured by St. Vincent authorities and were charged with immigration-related charges, to which they pleaded guilty. They are scheduled to appear in court Monday for sentencing. 

Evidence discovered on the Simplicity suggests there were “acts of violence,” Simmons said. Investigators found what is believed to be blood on the boat, and items were strewn around. 

Roberston, Stanislaus and Mitchell were charged last year with one count of robbery with violence. Mitchell also faced rape charges, authorities said. 

Children cling to hope

The couple’s children, Nick Buro and Bryan Hendry, said in a statement Tuesday they remain optimistic in the search for their parents, who “lived a life that most of us can only dream of, sailing the eastern coast of the United States, living on their home Simplicity , making friends with everyone they encountered, singing, dancing and laughing with friends and family.”

Buro and Hendry said they were coordinating with the United States Embassy, American officials and the governments of St. Vincent and Grenada.

“While the end of their life may have been dark, they brought light, and that light will never be extinguished from the hearts and minds of the people who knew, loved and cared so deeply about them,” the children said. 

Hendry and Buro said in a Saturday statement they “applaud the St. Vincent authorities for their quick actions in securing Simplicity and their brave, swift response that led to the apprehension of three dangerous fugitives.”

Simplicity discovered by ‘good Samaritan’

The Salty Dawg Sailing Association, an educational nonprofit based in Rhode Island, said in a Feb. 22 statement that Executive Director Tatja Hopman learned the Simplicity was found anchored and abandoned on a St. Vincent beach. 

A “good Samaritan” boarded the boat and discovered evidence of violence. Longtime SDSA members Hendry and Brandel had sailed the boat in the 2023 Caribbean Rally from Hampton, Virginia, to Antigua. The couple decided to spend the winter cruising the Caribbean, the association said. 

The association has a tracking map where they can follow members’ boats. Simplicity’s tracking information shows that the boat was anchored in Grenada before sailing to its last anchorage in St. Vincent, the association said.  “I have spoken to the families and have offered our deepest condolences and our assistance in any way possible,” said SDSA President Bob Osborn. “In all my years of cruising the Caribbean, I have never heard of anything like this.”

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What are the most popular months to visit the Caribbean?

December through April is often regarded as the best time to visit the Caribbean. It's when temperatures are mild, rainfall is minimal and humidity is at its lowest. This is the region's tourism peak season, meaning airfares are generally higher. Travelers tend to avoid the months of June to November, which is the hurricane season. But you'll still find places that are rarely affected by this, including Aruba, Barbados, Curaçao and Trinidad and Tobago. If you want to avoid the crowds and land bargain Caribbean flight deals, try the shoulder seasons of May to June and November to December. A combination of fewer tourists and great weather promises an idyllic Caribbean getaway.

Which airlines fly to the Caribbean?

This exciting vacation destination is served by a number of leading airlines. American Airlines , JetBlue Airways and United Airlines are among the more popular carriers that will get you from the United States to your island paradise. Enter your departure dates and destination into Expedia to see a complete list of airlines offering affordable tickets around the region.

What are some of the best places to visit in the Caribbean?

Whether you want to kick back on white sand beaches, try watersports in crystalline waters, tour historic monuments or dance to the rhythms of calypso, the Caribbean has an adventure for everyone. Delve into the region's fascinating past at places like the UNESCO-listed Old San Juan, Puerto Rico and the Dutch town of Willemstad in Curaçao. Or, take the plunge at Dunn's River Falls, Jamaica and Stingray City, Cayman Islands. With an aquarium, casino, private beaches and a waterpark, there's fun for all ages at Atlantis Paradise Island, Bahamas. Be sure to also explore some of the Caribbean's most impressive natural attractions. The Pitons, St Lucia and The Baths, British Virgin Islands are just the start of the wonders spread throughout the archipelago.

What are some of the Caribbean's most popular airports to fly into?

Grantley Adams International Airport (BGI) , Luis Muñoz Marin International Airport (SJU) and Sangster International Airport (MBJ) are among the most popular airports to fly into. You'll find flights to these terminals and other Caribbean destinations from major cities located across the United States.

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STEM skills at work: International Yacht Restoration School offers chance for second career

NEWPORT – Full-time teacher to full-time student? Seeking a new career at age 55?

Nick Willis of Providence didn't rush into this life-altering decision. He said he and his wife, nurse practitioner Heather Glenn, like to carefully weigh all factors before making their decisions. In this case, once they put all relevant information on the scale, the decision, while pushing them a tad out of their comfort zone, was clear.

This past September, with a long career as a software engineer for Raytheon and, most recently, two very satisfying years teaching mathematics at the Blackstone Academy Charter School in Pawtucket in his rear-view mirror, Willis showed up at the IYRS School of Technology and Trades, enrolled in its six-month Marine Systems program.

He recently completed the on-campus program and is now honing his electrical systems drafting skills, and making a few dollars again, in the school's externship program.

Willis said he had a “great career” at Raytheon and labeled Blackstone Charter teaching the best job he's ever had. He said the students were amazing, the faculty passionate, and the leadership committed to maintaining “a wonderful school." Leaving BACS was not done without emotion.

“IYRS really tugged at my heart, though, and I felt it would create an opportunity in the future to be teaching something a little bit more pragmatic than factoring quadratic equations,” Willis said. “There's a lot of talk about the importance of STEM. Well, if you want STEM, you need look no further than a marine diesel engine or electrical system.”

How the International Yacht Restoration School programs work

IYRS was founded, in 1993, as the International Yacht Restoration School. Founders Elizabeth Meyer and John Mecray envisioned a a true wooden boat restoration program. The school over three decades has grown to now offer four programs of study – boat building and restoration (20 months), composites technology (9 months), digital modeling and fabrication (9 months), and marine systems (6 months). All four programs have been accredited by the Accrediting Commission of Career Schools and Colleges.

According to Julia McCann, IYRS director of marketing, the majority of the school's students are career changers, and the externship program is a key component of making the switch effective for students. She noted that IYRS collaborates with highly-regarded industry partners for both externships and job placement. Students and alumni can access the IYRS job portal. The school, she said, has an 85 percent job placement average for grads, with hobbyists accounting for a portion of the 15 percent.

“IYRS graduates typically excel fast in their new careers,” she said, “rising to new roles and opportunities with their employers.”

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In a blog post on the IYRS website, Willis noted that marine systems students enjoy multiple field trips to boat yards, electronics shops, and suppliers and get to hear from guests speakers and enjoyed a career day filled with employers from Maine to California. One day, he said, three vice-presidents from nationwide Safe Harbor Marinas visited the students. The students, he said, also had the pleasure of Al Thomason, co-founder of engine-base charge control company Wakespeed, spending a day with them.

The IYRS' very concentrated education model – essentially five full work days per week – rapidly takes students from Day 1 to work force ready. Willis said that with their savings and his wife's income and some spending adjusting when needed, they were able to financially handle his paying for school and being out of work for half a year. They saw it and now see it as a wise investment. He described his wife as “incredibly supportive” during the new career adventure.

Students of all ages and experience levels

Willis said his fellow IYRS students included those right out of high school as well as people retiring from the Navy and Coast Guard. He said he immensely enjoyed the support of his cohorts. Some of his fellow students are taking a career paths to Maine, to the Caribbean, with others sticking around to help continue the state's history of master boat building.

Willis said he was experiencing some nerves leading up to his back-to-school start date. Those nerves were soothed, he said, on Day 1 when IYRS brought all the students into the boat building and restoration area and emphasized the inclusive school culture. That, he said, was followed by two weeks of message reinforcement.

“They could write the book on what it takes to create a safe learning environment, and I don't just mean safety with tools, although they are good at that, too,” he said.

Combining technical knowledge with practical skills

Born in England and raised on Massachusetts' North Shore, Wills said that while he lived most of his life near the ocean, his passion for boats and the maritime world did not surface until 2020. Due to COVID, he and his wife were itching for outdoor activities. They took sailing lessons. (“She enjoys it, I'm a bit of a nut about it,” he said.). They subsequently bought a 37-foot sailboat built in 1999.

When he was teaching algebra and pre-calculus at Blackstone Valley Charter School, Willis said that when he showed students pictures of some of the electrical work he was doing on his boat, some of them said they weren't smart enough to do such work. Wills said he knew his students were plenty smart enough, and got him thinking seriously about IYRS and that perhaps what he really should be doing is helping children connect into the maritime trades.

That dream still lives.

“I am exiting the Marine Systems program with what I feel is world class fundamental skills as a marine electrician/mechanic,” he said. “There is huge demand out there for this, with the opportunity to become highly skilled and specialized.

“I still want to teach, and eventually would like to be involved in a 'semester-at-sea' style program that is accessible to kids who may not have had the chance to be out on the water, and also includes a maritime trades element in the curriculum.”

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The cost of the marine systems program starting in the fall is about $25,700. Federal financial aid and other grants and scholarships are available.

Willis said the starting pay for marine systems graduates ranges from $25 to $30 per hour. He said he plans to work part-time and then enter the IYRS' 20-month Boatbuilding and Restoration Program. Local boat builders, he said, have told him marine systems plus BBR is a “highly desirable combination.”

“Nick’s story,” McCann said, “is typical in that most of our students are seeking to align a passion or interest to work with their hands with a way to earn a living or follow through on a life-long dream. In Nick’s case, he was initially looking to combine his love of teaching with his passion for sailing. After completing IYRS’s marine systems program, he is exploring other opportunities that he wasn’t aware of prior to enrollment.”