charter sailboat in caribbean

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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

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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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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

The Barefoot Lifestyle – No Shoes, No Stress, No Mess

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

Sonder Seawind 1260

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

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.

Rob Roy CATANA 531

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.

HAPPY Melges 20

SMILE (#212) Melges 20

SALT FISH J 24

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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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:-

SOUTH. Get ready for adventure when you step on board the 180' mega yacht South. You and your guests will find plenty to do, as she offers plentiful spaces for lying out to enjoy the sun, enjoying a movie or game in the sky lounge, working out in the Techno gym with an amazing view, or enjoying the on deck Jacuzzi and watersports. See SOUTH:-

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:-

LIQUID SKY. The 67' sailing catamaran Liquid Sky was launched in 2024 by Fountaine Pajot. With four cabins, she accommodates as many as eight guests, and offers a number of places for you to hang out and enjoy the journey, including on the bow soaking in the in deck Jacuzzi, up on the flybridge taking in the views, or on the aft deck with al fresco dining. See LIQUID SKY:-

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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783  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.

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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 $1,061,000 p/week ♦︎

115m Lurssen

115m   2021

from $2,831,000 p/w eek ♦︎

Black Pearl 14

105m Oceanco

105m   2018

Christina O 34

99m Canadian Vickers

99m   1943/2020

from $750,000 p/w eek ♦︎

Carinthia VII 12

97m Lurssen

97m   2002/2023

from $1,524,000 p/w eek ♦︎

97m Feadship

97m   2017/2022

from $1,715,000 p/w eek ♦︎

CC-Summer 12

95m Lurssen

from $1,286,000 p/w eek ♦︎

93m Feadship

from $1,501,000 p/w eek ♦︎

Aquarius 12

92m Feadship

from $1,500,000 p/w eek

Queen Miri 36

92m Neorion

92m   2004/2023

from $1,061,000 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

90m   2018/2024

from $1,299,000 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 $531,000 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   2018/2024

from $980,000 p/w eek ♦︎

Victorious 12

85m Ak Yachts

from $871,000 p/w eek ♦︎

Le Ponant 32

84m   1990/2022

from $488,000 p/w eek ♦︎

Savannah 12

84m Feadship

84m   2015/2020

from $1,072,000 p/w eek ♦︎

Alfa Nero 12

81m Oceanco

81m   2007/2021

from $728,000 p/w eek *

Elements 12

80m Yachtley

from $859,000 p/w eek ♦︎

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 $811,000 p/w eek ♦︎

from $480,000 p/w eek

Huntress 12

76m Lurssen

76m   2009/2022

from $725,000 p/w eek

75m Admiral Yachts

from $965,000 p/w eek ♦︎

75m Feadship

from $900,000 p/w eek *

75m Abeking & Rasmussen

from $880,000 p/w eek

Starburst IV 12

from $984,000 p/w eek ♦︎

74m Nobiskrug

74m   2008/2013

from $561,000 p/w eek ♦︎

73m Delta Marine

73m   2006/2015

from $525,000 p/w eek

Nautilus 12

73m Picchiotti

from $803,000 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 $595,000 p/w eek ♦︎

69m Feadship

69m   2012/2019

from $600,000 p/w eek ♦︎

Sycara V 12

68m Nobiskrug

68m   2010/2017

Wayfinder 12

68m Astilleros Armon

from $375,000 p/w eek

67m Icon Yachts

67m   2010/2020

from $540,000 p/w eek

67m Alloy Yachts

67m   2011/2019

from $354,000 p/w eek ♦︎

67m Benetti

from $680,000 p/w eek

67m Shadow Marine

67m   2007/2008

from $120,000 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

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 *

Lady Britt 12

63m Feadship

from $465,000 p/w eek *

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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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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.

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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.

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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.

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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.

Yacht Charter Bookings

St. thomas, virgin islands, tel: 340-774-5630.

Email: [email protected]

• Power Yachts
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• Destinations
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• Yacht Charter FAQs
• Sample Yacht Charter Itinerary
• All Inclusive Yacht Charters
• Spend the Day on a Yacht Charter
• Why choose a Yacht Charter vacation?

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
• Create Your Own Custom Itinerary
• Visit Untouched Islands
• Different Caribbean Destinations
• Unforgettable Memories
• Fully Prepared Meals by Your Own Private Chef
• Underwater Adventures with Sea Life

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

• 157′ Mega Yacht
• 2 Kings, 2 Queens,
• 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
• St. Thomas, USVI
• 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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BVI, USVI & CARIBBEAN YACHT CHARTERS

We've been arranging extraordinary crewed yacht charters in the British Virgin Islands (BVI) , US Virgin Islands (USVI) , Bahamas , and other Caribbean destinations for over 25 years. Much more than a vacation...our private, all inclusive crewed yacht charters are an Experience!

Kick off your shoes, step aboard your luxury yacht charter, and leave your everyday cares behind. Your professional crew will take it from there, curating an itinerary and daily experience with your personal pace and whims in mind. The perfect blend of adventure, discovery and relaxation, you can choose to do as much or as little as you want. Enjoy pristine white sand beaches, all the latest watersports, warm turquoise waters, authentic beach bars, on-board luxuries, custom-tailored menus, world class snorkeling, and more. Set sail on one of our BVI yacht charters and every day will become as unique as each of the islands you’ll explore.

Call us in our South Florida office at 954-980-9281 or Request a Quote . We'll quickly match you with a charter that fits your budget, style and interests plus effortlessly guide you towards your vacation of a lifetime.

Charter Areas

We focus on crewed charters and our specialty includes the British Virgin Islands (BVI), US Virgin Islands (USVI), Bahamas, and other Caribbean destinations. Select from our ever popular BVI catamaran charters which can include convenient flights into Tortola, BVI, St. Thomas, USVI or through San Juan, Puerto Rico. Or consider one of our other charter destinations , including our authentic charters in the Grenadines or a more remote charter feel that you'll find in the Bahamas .

BVI British Virgin Islands

Bvi: british virgin islands.

The Exumas Bahamas

The exumas, bahamas.

The Grenadines

Yacht Options

We know our yachts and crews and pride ourselves on being personally familiar with the destinations we cover and more importantly, with our distinctive list of fully crewed yachts. Choose from our extensive lists of yacht recommendations, including our popular crewed catamaran charters , our modern power catamaran options , plus our high-end, luxury motor yachts selections . Not sure which yacht style suits you best? Learn more about the various yacht style options .

Power Catamarans

Motor Yachts

Charter Types

We make it a priority to match our clients with ideal crews. We get to know our clients and what's most important to them in order to match them with the best yacht and specifically crew for their charter. We'll align you with the perfect crew for a family yacht charter , a crewed sailing vacation for a group of couples , or a charter yacht vacation for a milestone birthday or anniversary . Learn more about all of our Charter Types .

Family Charters

Couples Charters

Anniversary Charters

Specialty Charters

Is on-board scuba diving , a Chef that can cater to a group of foodies , or the ability to accommodate an extended family or corporate group key? Regardless of what you're specifically after, our time-tested process and unique experience continues to effortlessly guide our clients towards the best yacht & crew for their family or group of friends and then ultimately, on to carefree memories that will last a lifetime. Learn more about our various Charter Types .

Tandem Charters

Foodie Charters

Dive Charters

A multi-repeat client & group of couples that we booked aboard 62' Catamaran Serenity Now in late April 2022 said:

Hi Lynne, Sorry for the slow response, it’s been a little difficult to get in the swing of things since leaving paradise! Once again, your recommendation and direction in planning this charter was spot on! Your help in navigating the charter flight to making sure we had all the COVID testing in place, we were well prepared! The BVI’s are just so amazing. I do believe it’s my very most favorite place on Earth. Lynne, I can’t thank you enough for contacting us when the Serenity charter became available. We look forward to many more fabulous charters with Carefree Charters! Thank you again, Kelley & David M., Texas

WHY CHOOSE CAREFREE?

Because Experience Matters. We're a long-standing top 5 Crewed Yacht Charter Company with over 25 years of industry experience. Our Team's tenure includes 16 years in business as professional Yacht Charter Brokers plus a combined 25 years of experience as professional Crew while aboard various highly successful yachts in the BVI, USVI & Caribbean. When combined, Your Team at Carefree Yacht Charters is uniquely qualified to expertly handle your vacation of a lifetime. Learn more About Us and the Carefree Difference .

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Sail the Caribbean

• Location Guide
• Sample Cruise

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

Sailing charter versus resort stay: comparing the costs

A sailing holiday frequently combines with a land-based resort stay. How many nights aboard charter boat and how many nights onshore, or foregoing one or the other due to cost, is often a discussion point. So we did an exercise on the price comparisons between boat and resort. The cost benefits of a sailing holiday are clear

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.

The Sail Connections Guarantee

One contact - every option - advice you can trust.

• Matching any competitive offer
• Sourcing boats with discounts available
• Personalising our proposal just for you
• Qualifying the operator as well as the boat
• Advising without bias based on 25+ years of experience
• We do more than just book yachts!

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 packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.

Your  VOYAGE  Awaits!

Eat, shop, and play while you are onshore., voyage 590 best charter boat.

A private, luxury, Caribbean sailing vacation

VOYAGE Charters invites you on a private, luxury, Caribbean vacation. Our yacht charters include Bareboat, Yacht & Captain, and All-Inclusive Crewed. Let our friendly staff, captains, chefs, and concierge services help you experience the perfect sailing vacation in the British Virgin Islands.

Modern, luxury,  private yachts

Compare our  voyage charters.

• Meals & Bar

Yacht & Captain

All inclusive crewed, all voyage yachts have water makers., explore your  charter experiences, things to do.

Explore Things To Do in the British Virgin Islands while on your next VOYAGE Charter.

Explore the British Virgin Islands Islands while on your next VOYAGE Charter.

Captain, chef,  and provisioning

Select our  voyage services.

• Provides Professional Service
• Conducts Safety Briefing
• Creates Customized Itinerary
• Operates Yacht & Tender
• Facilitates Water Sports Activities
• Keeps Yacht Clean and Organized
• Creates Customized Menu
• Caters to Dietary Requirements
• Provides Full Provisioning Service
• Prepares Gourmet Meals & Drinks
• Keeps Yacht Clean & Organized

Provisioning

• Shop in Store
• Shop Online with Free Delivery
• Hire a Chef to Shop and Pack Away
• Pay for Receiving and Packing Only
• Pre-Packaged Meals Service
• BVI Market Locations

The perfect  yacht charter

PLAN YOUR NEXT ADVENTURE

Book an unforgettable yacht charter vacation

Sail Play Dine Yacht Charters is here to help you plan a trip you’ll never forget. Experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed charter yacht in the US and British Virgin Islands, Bahamas, and beyond! We take care of your every need to match you with the right boat and crew at the best rate guaranteed . We offer a large range of boats that suit every budget and our trusted service comes at no extra cost to you !

Crewed Yachts

FIND AND CHARTER A CREWED YACHT 

Destination

HOW IT WORKS

1. describe your dream trip.

Tell us about your perfect vacation. Destination, preferences, budget, who will be joining you, and what you would like to see and do.

2. RECEIVE A PROPOSAL

Our team will be in touch with an initial proposal that we’ll refine together. The yacht charter vacation proposal will include our top recommendations tailor-made to match your interests.

3. BOOK YOUR PERFECT VACATION

Once you decide on your preferred yacht, we can put a complementary hold to secure your dates while you finalize your travel plans. Complete your reservation by paying a deposit fee.

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BOOK WITH CONFIDENCE. NOW, AND FOREVER.

Whether you want to book an escape for right away or for the end of next year, we can arrange it. Just let us know when and where you want to go, and we’ll do the rest. That’s why we’re here. Ready to help. Ready to reassure. And ready to get you the trip you deserve.

Download the ultimate all-inclusive yacht charter vacation guide. 

Why choose sail play dine.

SOME OF THE REASONS TO BOOK WITH US

WE'RE A FEE-FREE SERVICE

Our trusted service comes at no extra cost to you ! Our commission is paid by the yacht owner and there is no additional cost to you.

WE'RE FULL OF IDEAS

Our recommendations are personalized and hand selected. We look forward to working with you to make the right choice.

WE'VE GOT YOUR BACK

We are with you every step of the way. Before, during and after your vacation, to make sure it is unforgettable. We are available 24/7 by phone, text, whatsapp, social media or email. Or you could send us a message in a bottle, and we’d respond to that.

WHERE WOULD YOU LIKE TO GO

BRITISH VIRGIN ISLANDS

The British Virgin Islands’ sprawling volcanic archipelago is the true essence of the Caribbean. Here, relaxation and discovery go hand in hand among the mango trees, coconut palms and silky beaches. Adventure is at the drop of an anchor as you set foot onto uninhabited islands during island-hopping escapes and witness an underwater world of unspoiled reefs and unique wreck dives.

US VIRGIN ISLANDS

The Virgin Islands is a great sailing vacation destination for first time sailors and families as there are many crewed private yachts available to charter and the light trade winds and protected bays make for a fun, safe playground for kids and adults alike.

Pristine beaches, warm blue seas, and sizzling scents – the Bahamas, the super tropical neighbor of nearby Florida, are a luxury traveler's dream. And with more than 700 islands and 2,400 cays, this is a true Caribbean playground.

ST VINCENT AND THE GRENADINES

A cluster of islands each more breathtakingly beautiful than the last, St Vincent and the Grenadines has always been there to indulge our need to island hop. Bequia, Canouan, Mayreau, Petite St Vincent, the Tobago Cays; we can think of nothing better than a luxury vacation in the Grenadines spent sailing around these stunning islands where our only concern would be where to drop anchor for an afternoon swim.

What Does Your Dream Caribbean Vacation Look Like?

Explore the possibilities aboard a luxury crewed yacht.

Yacht Search

Why charter the caribbean.

Indulge in the ultimate Caribbean escape with a crewed yacht charter. Charter the Caribbean and you will expereince crystal-clear waters lapping against your private yacht, a professional captain navigating hidden coves, and a personal chef whipping up gourmet meals.

With more than half a century of sailing expertise, extensive captaincy experience spanning over a decade, and nearly 30 years crafting personalized yacht charters, we offer unparalleled service to guide you towards the perfect Caribbean adventure.

Our Destinations

Charter the Caribbean on a luxurious crewed yacht. Explore breathtaking destinations at your own pace.

The Caribbean’s Tranquil Paradise

Central America’s Crown Jewel

British Virgin Islands

Nature’s Little Secret.

Virgin Islands Charm with Rich History

St. John USVI

History, Nature, and Luxury

Tiny Paradise with a Big Surprise

Charter the Caribbean

Specializing in unique cruising vacations that you’ll remember for the rest of your life.

What you’ll get when you plan a trip with Charter the Caribbean:

Attentive, first-class service provided by your dedicated captain and crew.

Input into the planning of the itinerary, menu, and onshore activities.

Delicious, gourmet meals prepared by your personal chef.

Open bar for beer, wine, and spirits with our all-inclusive charters.

Sailing, snorkeling, windsurfing, and kayaking instruction on many of our crewed yachts.

Ability to make your crew selection the priority when choosing a yacht.

Access to pristine beaches and secluded coves that large cruise ships can’t reach.

Complete privacy

Highest safety standards.

Expert assistance with all aspects of planning your cruising vacation.

New To Yachting?

If you’re new to yachting, our First Time Yacht Charter Guide is the perfect resource to help you navigate the world of luxury yacht charters.

First Time Yacht Guide

Whether you’re a seasoned charterer or new to luxury yacht charters, our comprehensive First Time Yacht Charter Guide is designed to assist you every step of the way.

Filled with frequently asked questions, a detailed boat comparison guide, real-life experiences, and visually engaging infographics, this resource is the perfect tool to educate yourself on the world of yacht chartering.

What Our Customers Say

Dive into the stories of our satisfied customers and discover why “Charter the Caribbean” translates to an unforgettable yachting adventure.

I’d give them 10 stars if it existed!!!

How could a trip like this, with a crew like Grant and Ulrika, be anything other than 5 Stars? I’d give them 10 stars if it existed!!! Every morning we were greeted with a fabulous array of beautifully cut fresh fruit and then day 1, the tastiest eggs benedict I’ve ever had. Day 2, pancakes, day 3, waffles! Day 4 breakfast tacos!!! All hand made. Gluten free options available too. Our party had a myriad of food intolerances and allergies, but Ulrika catered to us all without compromising quality or taste! She really should have a Michelin Star! Lunches and…

Let us deliver on your dream vacation.

Contact us to start a conversation about your dream vacation, and let us show you how we can help bring your vision to life through our exceptional yacht charter services.

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Destinations

All-Inclusive Crewed Yacht Charters

It's time to getaway relax escape cruise, all inclusive crewed yacht charters, british virgin islands | bahamas | st. martin | st. barts | the grenadines.

Starting at $60,000 p/wk

Starting at $42,000 p/wk

Starting at $21,400 p/wk

Starting at $28,790 p/wk

ALL INCLUSIVE

Crewed caribbean yacht charters, sheer yachting is a no charge booking concierge service for all-inclusive private, crewed yacht charters in the caribbean. each yacht has a permanent crew of at least 2 (captain & chef) or more depending on the size and amenities available onboard. your crew provides top luxury service, prepares all meals, and handles the yacht’s course. the knowledge of these experienced crew members make all the difference when perfecting a yacht vacation., sheer luxury, in any destination, from the alluring waters of the british virgin islands to the volcanic peaks of the grenadines, our crewed caribbean yacht charters are available wherever your bucket list takes you., what to expect, on your crewed charter yacht, our luxury charter yachts in the caribbean bring you an ultimate, all-inclusive vacation aboard your own private yacht. each of our boats is complete with a professional captain and gourmet chef. enjoy spacious accommodations, personalized itinerary, and premium amenities for your closest friends and family..

Many yacht rentals in the Caribbean rely heavily on charter yacht brokers, like Sheer Yachting, to book charters and handle the entire booking process. Finding an experienced and professional yacht charter broker is key, and this service comes at absolutely no charge to you!

Your sheer yachting charter broker, michelle, will facilitate the entire booking process between you and the caribbean yacht charter of your choice. with hundreds of yachts throughout the area to choose from, your broker’s extensive insight is pertinent to finding the perfect crewed charter yacht for your needs., check out our blog ....

Who Will be Onboard a Private Crewed Yacht Charter?

Nightlife Onboard a Crewed Yacht Charter

Sustainable Practices in Yachting

Booking is easy, with sheer yachting, find your yacht.

Let us know what you're looking for and we will find you the perfect match! We will contact the yachts to confirm pricing & availability.

Lock in your Dates

Reserve your charter dates by telling your broker to place a complimentary 10 day hold on the yacht of your choice.

sign a contract

Confirm your charter by signing a standard charter agreement and paying a 25% deposit. Then, do you happy dance; you're booked!

Get ready to go!

Fill out a preference sheet provided by your broker so your crew can stock the yacht with all of your favorite foods & drinks!

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Let's Get In touch

Fill out the contact form below and we will get back to you as soon as possible! Call +1 (954) 232-5884 for immediate assistance.

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Your Captain and Chef Charter

Captained sailing vacation.

Vacations are meant for relaxing and being afloat is no exception. Taking a charter skipper for a captained sailing vacation will allow you to fully enjoy your time on board without having to worry about itinerary, safe anchorages or systems on board. Even for the most experienced sailor, it’s nice to have some time for your mind to switch off!

This is your vacation, you can choose how involved you would like to be in planning the itinerary, hoisting sails or taking the helm. With a captained sailing vacation you can use your valuable skipper’s expertise to expand your own knowledge, and swap your best sailing stories and tips. Your skipper can be involved in your vacation as much or as little as you would like. It’s no problem to spend an evening ashore with family and friends, your skipper will make sure your vessel is safe and your cabins cool and air-conditioned for your return. If you are fascinated by the underwater world, then let your skipper guide you to the best snorkelling spots to point out lobsters hiding under rocks and lesser spotted marine life.

Enjoy all those painkillers with the knowledge that you’re not driving the dinghy at the end of the night. If you’d rather be in a bay with no one else around then your skipper can take you to spots that charter guests cannot reach so you have that unlit view of the milky way. If you’re looking for added adventure your skipper can show you hiking trails for exclusive island views, organize kiting lessons or take competent kiters to safe spots to launch from.

We pride ourselves at Horizon in only offering skippers that give you the full package. Our skippers are sailors, engineers, riggers, tour guides, entertainers, cocktail makers, deck washers, and DJs and will very likely be friends by the end of the trip.

If your idea of a vacation means staying out the galley during your trip then why not hire your own private chef for the week? Breakfast, lunch, and dinner are tailored to your personal taste. Your skipper and chef will work together to match food and itinerary whether that be local grilled fish Al Fresco under the stars or Jerk chicken wraps underway. Our chefs prepare a range of breakfasts, from tasty omelettes and French toast to more continental-style platters. Fresh local fruit is in abundance. Dishes could include blackened tuna, BBQ spicy steaks or Caribbean-inspired gumbo. To go along with this feast, you will have salads and other sides. Dessert could be something chocolatey and gooey; the best kind, or a cheese and fruit platter. We serve meals with a range of beverages, from healthy smoothies to wonderful wines.

If you would like to come away from your trip with ASA certifications, then check out our Horizon Sailing School page for more information.

Check out skipper

You’ve been up all day travelling and you’ve made it to paradise but now you’re boarding a boat you’ve never been on, on unfamiliar islands and suddenly you’re faced with hundreds of anchorages to choose from, water makers and in-mast furling systems.

Rather than spending your first day on the dock working out how everything runs, why not take a check-out skipper who can talk you through the systems as you use them?

Has it been a while since you picked up a mooring ball? Your check-out skipper can make sure that the first pick-up goes smoothly. Unsure about your itinerary? Go over the chart whilst watching the sunset and get real local knowledge on where to explore. Is this the biggest boat you’ve been on? Or have you spent years on a monohull but never manoeuvred a cat? Your check-out skipper can guide you through docking and moving in close quarters to build confidence for the week ahead. Taking a check-out skipper to your first anchorage or for the first 24 hours of your trip is the best way to start your vacation smoothly and settle into island time.

Call Horizon Yacht Charters now with your requirements, or Request a Quote here ,  and we will tailor-make the Caribbean sailing vacation of your dreams.

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Caribbean Yacht Charter: the Full Price List

The Caribbean is one of the most popular destinations for yacht charters, and it’s easy to see why.

A yacht rental in the Caribbean  because of its lovely temperature and gorgeous beaches, is a true sailing playground that includes legendary superyacht locations like Antigua , St. Barts, or the Virgin Islands .

But renting a yacht in the Caribbean doesn’t come free. Here are the main factors that influence the price of a yacht charter in the Caribbean, along with the most common price ranges you can expect.

Summary of Yacht charter price ranges in the Caribbean (USD per week incl. food and beverage)

What factors influence the price of a yacht charter in the Caribbean?

An individuals owner determines the price he wants to offer for his yacht while following the market. The pricing is based on metrics like the local demand, boat length,  category, crew number and the boat age. Along with this, there are several additional factors that might considerably affect pricing. These are as follows:

1.The yacht you want to charter: the main factor determining the cost of your Caribbean charter

The yacht is a significant component in defining the charter cost, although size is not the only determinant. A freshly introduced charter boat from a renowned builder with an experienced and well-liked charter crew will attract the highest pricing for its size class. Additionally, yachts with a renowned name or a legacy of famous ownership can charge a premium for their “fame.” And yachts with distinctive amenities like movies or unique water toys are also more expensive.

Furthermore, if a yacht has a space in its charter schedule, such as after an unexpected cancellation, certain brokers will sometimes provide a limited-time charter fee reduction.

Don’t make pricing the only factor when choosing a private yacht. It is essential to comprehend why prices are high or low for a particular yacht and accordingly make a decision.

2. The Caribbean destination itself: one of the factor influencing the price of a Caribbean yacht rental

In the Caribbean , there are over a thousand islands to select from, making it arguably the most excellent location for tropical yacht charters globally. You can charter in the Caribbean in three major regions: The Bahamas , the Greater Antilles, the Windward and the Leeward islands .

Depending on the charter type, the costs, amenities, and crew vary. As per your budget, comfort, and expectation, you may choose one that fulfills your idea of an ideal charter yacht. Here are some examples:

$2’000 USD is the minimum weekly price for a bareboat yacht rental

Bareboat charters are the most affordable alternative. You are responsible for fuel, food, and other expenditures, hiring the crew (or captaining the boat, if you’re licensed to do so), and paying the crew. Additionally, you may consider adding a skipper, hostess, or a mix of the two for bareboat charters. If you’re chartering a bareboat since you are licensed, you will be responsible for all aspects of navigating, sailing, mooring, and security.

Further, it is up to you to pick whether to cook or dine at local eateries along the road. Bareboat charters provide exceptional flexibility to explore whenever and wherever (weather permitting, of course), providing a unique vacation experience for the entire family.

At least one person in the group should be a seasoned sailor, or you may pre-arrange to have a captain on board if you’re visiting a new place for the first time and want to take it easy as a local guide down the coast.

$3’700 USD is the minimum weekly price for a skippered yacht charter

Skippered Yacht Charter is often a Bareboat Charter with the inclusion of a skilled, local Skipper who assumes full accountability for the safety of the boat, navigation, sailing, and anchoring. When floating, the skippers will gladly function as your guide and tour your various secluded harbors and anchorages that are often unfamiliar to most visitors. Subject to weather circumstances, he will pay heed to your desires of where you wish to travel and try his best to accommodate them.

Even if you are a novice, you will love learning to navigate the boat on your own with the assistance of a professional. It is a frequent assumption that a skippered yacht charter would cost significantly more than a bareboat hire. However, this is only sometimes the case.

$16’000 USD is the minimum weekly price for a crewed yacht charter

Crewed charter refers to a luxury charter rented with an entire crew. Generally, the crew onboard differs from charter to charter. Depending on their size, yachts may only have a captain and hostess/cook on board, or they may have a full complement of crew members, including a captain, engineer, deck assistant, experienced chef, and others.

Moreover, the bigger and more luxurious the yacht charter is, the better amenities you will experience. Fully crewed yacht rentals are ideal for individuals looking for an extraordinary and exclusive holiday of a lifetime. Onboard the fully crewed yacht rentals, and you will have a relaxing experience. You may make yourself as comfortable as you like. The personnel will give professional, five-star services while respecting your privacy and fulfilling your expectations.

Our tips to decrease the cost of a yacht charter in the Caribbean

A private yacht charter is a great experience, yet it can cost a fortune for some. What if we share a few tips to lower the costs of your yacht charter trip? Here are some:

Charter a yacht during the Caribbean shoulder season

Scheduling a yacht charter during the shoulder or off-season could save you up to half the price, even though sailing in the high season will guarantee the best weather. Yet, if you are a budget traveler or wish to experience charter at the best rates, consider booking at the shoulder reason.

Summer is the peak period in the Mediterranean, with the coldest months being January and February. If you want to save money, you should travel in the spring or fall, when the weather is milder and the water is warmer for swimming.

Excellent sailing conditions exist throughout the year in the Caribbean. However, hurricane season extends from June to November, with the peak of storm activity being between the middle of August and the middle of September.

Before making a reservation, evaluate your off-season location’s monthly mean temperature, rainfall, wind speed, and wind patterns. Stormy weather with high rainfall will not make a trip enjoyable. Hence, plan accordingly.

Pick a cheaper Caribbean destinations

The location, timing, and yacht charter firm you choose all have a significant impact on the cost. You can try and pick an island within the whole Caribbean easy for you to reach depending on where your departure country is. In fact it is easier to arrive in Saint Thomas than to Martinique from the USA, whereas from Europe it will be easy to reach Guadeloupe from France, or Saint Vincent or the United Kingdom with regular commercial flights. Be aware, that taxi planes exist, and can help in commuting between the islands. Popular Leeward islands like the Virgin Islands, Saint Barth or Antigua can be expensive to pick for. Yacht charter during the holidays season, and during popular events such as the Heineken Regatta. So you may want to choose to sail towards the grenadines in May for example, which is a wonderful cruise to do.

Choose a smaller yacht with a smaller crew

Small yachts may be inexpensive, straightforward, and seaworthy. Additionally, their small size makes them cost-effective sailboats. Pocket cruisers are frequently available at a low cost. Further, they don’t require a big crew to maintain and operate. Hence, a small sailboat makes globe travel much cheaper!

Nearly all crewed catamarans and most smaller sailing monohulls offer all-inclusive charter pricing. The charter fee often comprises:

• Captain and Chef or Attendant
• Three daily meals and snacks every day aboard the boat.
• All beverages, including common wine, beer, liquor, and mixtures
• Temperature-controlled accommodations
• Watersports gear on board (scuba gear may be additional)
• Permissions for navigation, fuel, limited Wi-Fi, and all deck facilities

Extra fees for all-inclusive ships may include the following:

• Crew gratuities.
• Additional communications.
• Extra marina anchorages.
• Any meals ashore.
• Optional gear rental fees.
• Activities like scuba diving.

Read also: Luxury Crewed Yacht Charters – Frequently asked questions

If you’re looking to set sail on an unforgettable Caribbean excursion but not sure where to look for the best deals, have no fear! With a little bit of research, savvy shoppers can find great discounts and great offers and service from WI Yachts . Armed with knowledge about all payment structures involved in your chosen yacht rental option, it’s easy to avoid unwelcome surprises during checkout – leaving only one thing: smooth sailing for your dream vacation!

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Sailboat rental Caribbean

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Renting a sailboat in the Caribbean & discovering Bahamian or BVI’s Coasts, what are your needs? We will find the perfect yacht for you. Get your offer! 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: Caribbean useful information , Which period is best to sail in Caribbean? . Get some inspiration from the Sailboat rental Caribbean itineraries tab and start planning your next sailing itinerary, read detailed descriptions of Caribbean sailing destinations , or Caribbean sailing articles.

How much does a sailboat rental Caribbean cost?

Caribbean useful information, which period is best to sail in caribbean, sailboat rental caribbean itineraries.

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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.

Can you rent a sailboat in the Caribbean – do I need a license?

In the Caribbean, a license is not specifically required. You simply need to fill out a sailing resume and only charter a yacht that your experience permits. Before you confirm your sailing trip to the Caribbean, please send us your sailing experience, or a copy of your skipper licence and we will check it for you. If you do not have a skipper license, or experience it is also possible to rent a sailboat with a skipper

Sailboat charter in the Caribbean – the main ports

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 for sailboat charter 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. Exumas sailing , Exumas boat rental

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. Eleuthera sailing , Eleuthera sailing adventures sailing in the Bahamas , Bahamas boat rental

Sailboat yacht charter in the BVI – the main ports

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. Tortola sailing , Tortola yacht rentals

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. Virgin Gorda sailing , Virgin Gorda yacht charter BVI sailing , British Virgin Islands yacht rentals

The most popular ports for sailboat charter 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. sailing Puerto Rico , boat rental Puerto Rico

Sailboat yacht charter in Mexico – the main ports

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. sailing Mexico , a title=”Rent a boat in Mexico ” href=”https://boattheglobe.com/destinations/caribbean-yacht-charters/mexico” rel=”noopener noreferrer”>yacht rental Mexico

The most popular ports for sailboat charter 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. Cuba sailing , yacht charter 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 Caribbean sailing routes .

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.

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 [...]

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.

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.

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Sailing boat rentals in the Caribbean

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Sailboat Rental in the Caribbean

The Caribbean is an idyllic island destination with a vibrant and authentic culture. With a warm tropical climate through winter, steady sailing winds and a range of some 7,000+ outstanding islands to hop between, you can choose everything from uninhabited and remote outcrops to bustling port towns with a swinging nightlife for your sailboat rental in the Caribbean. Although there's plenty of smooth and easy sailing to be had in the Caribbean, more adventurous opportunities await in areas like St. Martin, with open-water stretches and remote anchorages. You can choose from a wide variety of Caribbean sailboat rentals at good prices for your next sailing adventure.

A sailing paradise, paired with rich cultures, cuisines and traditions, the Caribbean is full of adventures and beautiful stretches of coastline where you can sail with your friends and family. No matter where you go, we can guarantee you a holiday full of adventure, when you go sailing in the Caribbean. Sail the British Virgin Islands and anchor in idyllic bays where you can stop for lunch or a cocktail on the beach. Snorkel with the tropical fish and turtles in the Bahamas and even encounter a swimming pig, or two! (Yes! We’re not joking!) Let yourself go as you sail with the wind in your hair and admire a constant panoramic view of breathtaking nature at its best. Rent a sailboat in the Caribbean!

How to Rent a Sailboat in the Caribbean

Sailboat rental in the Caribbean is easy and will only take a few minutes. Many visitors will choose to charter a sailboat for a week or more, either with a skipper or without, to fully explore the best of the Caribbean. As a region of colonial heritage, each island offers a unique blend of cultures. Whether that's Anglophone areas like the British Virgin Islands or Francophone Guadeloupe, it's best to choose one of the island areas to explore. You can choose to circumnavigate larger islands like Puerto Rico or stick to archipelagos and island-hopping.

How much does it cost to rent a sailboat in the Caribbean?

There are many different factors that can affect the cost of sailing the Caribbean seas, including the size, capacity, and type of boat, the season when you want to sail, the duration of your trip, and the number of people on board.  The price of Caribbean sailboat rentals will also be affected by whether or not you want to set sail with a skipper, as well as which extra services you want to add to your charter.  For example, you can usually choose to add a crew and watersports equipment to your charter for an additional charge.  

In general, though, sailing in the Caribbean will cost you at least $363 per day or $2542 per week in high season, and a minimum of $186 per day or $1304 per week in low season.

Can you go sailing in the Caribbean with or without a skipper?

Yes, it is possible to find a sailboat rental in the Caribbean either with or without a skipper.  However, you must keep in mind that if you want to charter without, you must be in possession of the appropriate licence. Sailing the Caribbean seas with a skipper and maybe even a crew is perfect for those who want a holiday where they only need to sit back and relax, watching as the spectacular shorelines of the Caribbean go past.  However, if you are someone who likes a little more adventure, bareboat Caribbean sailboat rentals where you can be the captain of your own boat will be a dream come true.

Sailing areas in the Caribbean

The Caribbean is a sailors playground, with an unlimited number of routes and potential itineraries. The British Virgin Islands may offer the best flexibility, with many islands within close distance from each other, offering plenty of opportunities to sail between 25 islands and take day excursions between glorious beaches and coves to a wealth of well-maintained ports such as Nanny Cay, Inner Harbour and Joma Marina. Alternatively, Grenada, St. Vincent and the Grenadines remains another favourite destination for experienced sailors, with gentle crystalline waters, alluring cays and paradisical islands. You should also consider Antigua and Barbuda, an area famed for its open sea races with plenty of small islands to visit.

Sailing boat rentals in the Caribbean are a popular choice of boat and can be found in the following areas of the Caribbean:

• British Virgin Islands
• Saint Martin
• Saint Vincent and the Grenadines
• Antigua and Barbuda
• Saint Lucia

Itinerary Ideas in the Caribbean

Lacking inspiration for your sailboat rental in the Caribbean or simply need some tips? Check out our Nautal blog for sailing routes around the BVI, Martinique, Guadeloupe and much more! We calculate nautical miles in our routes and give restaurant recommendations in addition to other random facts and cool things you can do in the area.

Climate and Sailing Conditions in the Caribbean

Our favourite time of year is spring and early summer, from March to June, when the islands are in bloom and are a pleasure to sail. The trade winds are perfect at this time of year, though Christmas and Thanksgiving are also popular times of year for sailboat rentals. We do not advise sailing in August and September as this is known as hurricane season and various areas are not safe during this time of year. 

When is the best time to rent a sailboat in the Caribbean?

As long as you avoid sailing in the Caribbean between August and September, you are bound to have a fantastic time.  Although many people look for a sailboat rental in the Caribbean over the winter months, we actually advise going in Spring and early summer.  From March until early June, the weather will be perfect for sailing and there also shouldn’t be too many tourists.  The reduced number of people means that you should be able to find better deals on boats.

How to get to your sailboat rental in the Caribbean?

The best way to reach the islands is usually by plane, or alternatively you can rent a sailboat in Miami or in the near Florida and sail to Caribbean areas such as The Bahamas.  Many islands have international airports and you can fly directly or find connection flights. 

Charter a sailboats near Caribbean

In Caribbean, privately owned boats are available for charter. See other boats located in the area.

Charter another boat type in Caribbean

Are you interested in other boats besides sailboats in Caribbean? Search for other boats to charter on our website

What’s the best Caribbean cruise line for me?

Jul 15, 2024 • 9 min read

Whether you're a family of four or a solo adventure junkie, the Caribbean has a cruise for you. Walter Bibikow / Getty Images.

It feels like just about everyone is headed on a cruise ship, and for good reason. There’s a real appeal to embarking on a getaway where your travel plans are already sorted; you only have to unpack once and arrive each morning in an exciting port of call.

Plus, new ships are rolling out incredible bells and whistles that push the limits of fun at sea (think indoor skydiving, roller coasters, and go-karts). At the same time, the cruise industry has shifted towards sustainable efforts that have emerged as fundamental to modern cruising. 

Recent statistics from CLIA (the official Cruise Line International Association) show an increase of nearly two million passengers in 2023 (totaling 31.7 million) compared to pre-pandemic numbers in 2019.

And there’s no more popular cruising region than the Caribbean , where upwards of 37 cruise lines with 154 ships rove the idyllic paradise of islands. With so many options, sorting out which ship and itinerary fits you best can be confusing. 

Here’s a handy guide to help determine which cruises are best for you, along with tips and advice to ensure you’re setting yourself up for a smooth sail. 

What Caribbean cruise is best for me?

Sailing for adventure.

Whether you're into ziplining through the rainforest, scuba diving one of the world’s largest coral reefs or swimming at the base of a waterfall, cruises throughout the Caribbean offer excellent opportunities for adventure.

Cruise ports known for high-octane activities include St-Martin (known for its superb scuba diving), Belize (cave-tubing and ziplining throughout rainforest treetops) and St Lucia (the Sapphire Falls Hike). 

Celebrity Cruises, Princess Cruises and Holland America have cruises that frequent these ports.

Best ships for families

Look for larger ships with kid-friendly pools, expansive kids' clubs and family-friendly entertainment. Royal Caribbean’s fleet features action-packed decks great for families with water slides, laser tag and mini golf. 

Disney Cruise Line’s fleet sails extensively throughout the Caribbean to ports that span from Cozumel , Mexico, to Willemstad , Curaçao. The line’s most common Caribbean offerings are shorter 3- and 4-night itineraries that are perfect for families looking for a short trip.

Cruise lines with private islands operate predominantly in the Bahamas , including Royal Caribbean, Disney Cruise Line and Norwegian Cruise Line. These stops are great family destinations as they feature enclosed, private environments with kids' activities and the ease of charging everything to your sea pass card.  

Singles at sea

Cruises can be an excellent place for singles to mix and mingle. A standard cruise stateroom rate is usually calculated at a minimum two-adult rate. Singles wishing to book a standard stateroom are typically charged a single supplement fee ranging from 50% - 100% of their base fare. 

As the demand for single cruise accommodations grows, new ship builds include solo staterooms, both interior and with balconies. Look to Celebrity Cruises, Virgin Voyages, and Norwegian Cruise Lines for some of the best accommodations for solo travelers. 

Most relaxing getaways

The most relaxing cruises sailing through the Caribbean tend to be the smaller ships focusing on a more “resort at sea” vibe. The higher-end ships with all-inclusive rates offer the luxury of seamless vacations. Windstar, Seabourn and Viking are the best lines for a relaxing cruise.

On these ships you’ll find daily activities that swap dance parties and poolside games for fitness-oriented activities like yoga and strength training classes, lectures on upcoming ports and ample lounge chairs to soak up the sun by the pool.

From your first step onboard, all your food and drinks (except for certain vintage wines and spirits), activities and sometimes your port excursions are included in your rate. 

Itineraries like the Viking Ocean Cruises’ West Indies Explorer sail a 10-day itinerary roundtrip from San Juan, Puerto Rico, with stops that include Tortola, British Virgin Islands; St. Kitts, Saint Kitts & Nevis and Roseau, Dominica. Rates for Viking Ocean Cruises include one shore excursion per port.

Best parties at sea

As the classic notion of cruising sunsets – goodbye white glove service, shuffleboard, Baked Alaska – a new era of fun is afloat.

Large ships are built to maximize fun, whether you're hopping pool parties, dancing the night away at late-night discos or cheering your team at rousing sports bars. Special interest cruises are also an excellent option for the most immersive fun at sea, whether that’s a full ship charter rock concert like the Rock Legends Cruise , a trip dedicated to Golden Girls fans , or an LGBTQ+ charter like VACAYA . 

Favorite lines that feature an upbeat party vibe include Margaritaville at Sea (particularly on their new Islander), Virgin Voyages and Norwegian Cruise Line.

A quick getaway

You’ll find cruise lines are leaning into shorter itineraries that offer weekend getaways to nearby ports in the Caribbean. Most of these sailings are roundtrip from Florida’s top cruise ports: Miami , Fort Lauderdale and Orlando (Port Canaveral). These are often 3- and 4-night sailings featuring a stop in The Bahamas or Bermuda . 

The vibe onboard is often more upbeat and celebratory, as guests do their best to maximize their limited time at sea. 

A few favorite lines for this style of travel include Celebrity Cruises, Royal Caribbean (who is launching Utopia of the Seas this summer as its first-ever large-scale ship that will exclusively sail short getaways) and Disney Cruise Line.

An extended journey through the Caribbean

Smaller cruise lines offer longer, extensive itineraries throughout the Caribbean; smaller ships can port far off the beaten path at more remote destinations. Itineraries like Seabourn’s “25-Day Captivating Antillean Treasures” sail to some of the lesser trafficked parts of the Caribbean including Marigot, St. Martin; Carambola Beach, Saint Kitts and Nevis; and Sopers Hole (Frenchmans Cay), BVI. Lines like Silversea, Windstar Cruises and Azamara are favorites that route to these idyllic destinations. 

When should I go on my cruise?

There are sailings throughout the Caribbean year-round, with high season running from November through April. This period is known for its optimal sailing conditions and weather. 

You’ll find cheaper sailings during the hurricane season, typically July through September, though you risk the chance of your trip being canceled or rerouted to avoid inclement weather. 

Holiday sailings (particularly during Thanksgiving, Christmas and New Year’s Eve) are also excellent times to sail as cruise lines curate impressive decor and holiday-themed activities.

How do I know if my cruise line is operating sustainably? 

Conservation efforts have become a vital tenet of the future of cruising, with the industry gearing towards carbon-zero sailings by 2050 . Efforts underway include ship engines that run cleaner on alternative fuels, advanced wastewater systems that can better clean sewage water and exhaust gas cleaning systems to improve air quality at sea and in port. 

Friends of the Earth’s Cruise Ship Report Card is a great resource to assess a ship’s sustainability efforts. 

A few lines at the forefront of sustainable sailing include Ponant, Disney Cruise Line and Hurtigruten. Ponant recently became the first maritime cruise line to receive Green Globe certification, which recognizes the line’s commitment to reducing its environmental footprint.  The line has shifted away from heavy fuel oil and installed catalytic systems to reduce atmospheric emissions.

Disney Cruise Line aims to operate with carbon emissions at net zero by 2030, in part by shifting to alternative fuels like liquefied natural gas (LNG) and hydrotreated vegetable oil. 

Hurtigruten is currently developing a zero-emission propulsion ship, which is aiming to be unveiled by 2030. 

There are still a large number of travelers who oppose the notion of cruise ships for not only their impact on the environment, but on local economies as well. Groups like Friends of the Earth , CLIA and Oceana are excellent organizations devoted to regulating the cruise industry.  

Need to know before you go

Here are some helpful tips to keep in mind when you’re booking a Caribbean cruise. 

Book in advance...

Cruise lines offer better rates further from your sailing date, often making sailings available to book more than a year out. The earlier you book, the better the selection of staterooms to choose from. 

Or take advantage of last minute deals

Cruise Plum is our go-to with a comprehensive overview of discounted inventories if you're angling for a last-minute getaway. 

Opt for third-party travel insurance for hurricane season protection

Travel insurance is the best way to ensure smooth sailings on your Caribbean cruise. Typical cruise insurance rates hover around 5 to 10% of your total trip cost. 

Don’t just opt into the cruise line’s designated insurance option; shop around on a platform like Squaremouth for the most value. 

Look for a plan specific to cruise travel, with coverage that includes compensation for delays, cancellations (particularly helpful during hurricane season), emergency medical, and the premium option of canceling for any reason (CFAR). 

Be hurricane-aware

Hurricane season in the Caribbean is typically July through September. The outlook for the 2024 season from NOAA’s (National Oceanic and Atmospheric Administration) predicts an 85% chance of an above-normal season with the potential range of 8-13 hurricanes with winds of at least 74 mph. 

Cruise lines work expeditiously to avoid sailing into the path of any major tropical storm or hurricane, often rerouting or shortening itineraries as threats arise. Cruises rarely encounter major storms as they’re able to chart the course of the weather and route accordingly. 

In the event you encounter a major storm while at sea, head to the middle of the ship where you’ll feel the rolling of the ship less, take over-the-counter aids like Dramamine or Bonine and keep your eyes on the horizon for stability balance.

You don’t necessarily need a passport 

Passports are not required for closed-loop sailings that begin and end at a US port. All you need is a boarding pass, a government photo ID (if you’re 16 years or older) and a certified birth certificate or certificate of US naturalization. 

However, keep in mind that you might not be able to disembark the ship at certain ports (those ports include Barbados , Martinique and St-Barthélemy ).

Third-party excursions can be a better value play

If you want to stretch your dollar further, consider booking with local tour operators before arriving at each port. It’s important to note that third-party excursions are the best when they’re morning-only activities. 

The ship won’t wait for you if you’re late returning from a third-party excursion. For full-day excursions, consider the line’s offerings, as the ship will wait for you, and there’s nothing worse than missing the boat.

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VIVACE Shines at the 2024 Newport Charter Yacht Show

Posted July 16, 2024 in Charter by Eileen Lopez

The annual Newport Charter Yacht Show, with its nearly four-decade history, consistently impresses as it graces Newport, Rhode Island’s iconic waterfront. This year’s event showcased 15 luxury motor and sailing yachts, ranging from mid-60 feet to over 100 feet in length. Northrop & Johnson proudly presented the stunning 102’ (31m) Alpha motor yacht VIVACE at the show. This Italian-built Spritz 102 model stands out in the market, offering an unparalleled platform for guest entertainment. VIVACE’s exceptional alfresco areas and an energetic, charter-savvy crew ensured unforgettable onboard experiences filled with fun and adventure. The Newport Charter Yacht Show is a prime opportunity for yachts to demonstrate their capabilities in delivering bespoke charter vacations to prospective charter brokers.

VIVACE was a highlight of the show, earning accolades across several competitions, including Best Overall Tablescape, 2nd Place in the Chef Competition (with Chef Monja Jacobs), 1st Place in the Crew Fender Challenge and 2nd Place in the “Stew Try Outs” Crew Challenge.

In the Chef’s Competition, chefs were given a “mystery basket” of ingredients just 24 hours before presenting to a panel of three judges. Cooking and heating were performed in the yachts’ galleys, but plating, saucing, and garnishing took place on a staging table under time constraints. Chef Monja Jacobs of VIVACE impressed the judges with her “Scallops and Scapes” dish.

VIVACE’s “Coastal Gardens” tablescape won first prize, judged by professionals from Newport Yacht Interiors. Head judge Cheryl DiGennaro praised the crew’s enthusiasm and creativity, noting their effort in sourcing and custom-decoupaging oyster shells. The table’s styling complemented the yacht’s design, creating a welcoming atmosphere for comfortable conversations with personalized details.

Monday evening’s Crew Competitions, a highlight of the social schedule, featured captains and deckhands attempting steward tasks, inflating fenders and making flower arrangements, all timed to simulate the pressures of chartering. A VIVACE crew member excelled in the fender competition, preparing a 5’ fender with an electric pump in just 54.22 seconds.

For more information on chartering the motor yacht VIVACE, please contact your preferred Northrop & Johnson charter broker.

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How to Charter a Boat

If you want to sail off into the sunset, at least temporarily, you need to understand how to get aboard first.

By Lauren Sloss

This time of year, it’s an inevitable thought: Life would be that much better out on the water. Specifically, on a boat.

Even if you have neither a boat nor boating experience, it’s never been easier to make your nautical dreams come true — whether you want a day trip on your local lake or a fully staffed multiday voyage in a far-flung locale. Here are the initial questions that will help you plan an adventure on the water.

Whom are you traveling with?

Thinking about the size and dynamic of your group is an important first step, even if you are simply going on a day trip. Will children be on board? How old? What about elderly parents?

Dan Lockyer, the chief commercial officer of Dream Yacht Worldwide , strongly encourages travelers to determine group size — and, ideally, get people committed — before booking.

“The location that you want to go to, the time of year that you want to go, the type of boat that you want will entirely depend on the makeup of the group that you’re sailing with,” Mr. Lockyer said.

Do you want to captain, or do you want a captain?

Different charter companies specialize in certain locations, types of boats, itineraries and services. Some companies offer the opportunity for a “bareboat” charter, in which you rent the boat and take on the navigation and provisioning yourself, while others exclusively offer fully staffed options, including a captain and a cook.

If you want to captain the boat yourself, almost all outfits require some kind of proof of sailing or boating experience, often in line with local regulations.

Edward King, 45, an executive at a streaming company based in San Francisco, is experienced in sailing the city’s waterways. But on vacation, he said he would prefer to let a captain and crew take the lead.

Mr. King said he appreciates a captain who is familiar with both the local waters — “they’ll know how to avoid sailing into a certain sandbar,” he said, — as well as the local attractions.

In contrast, Matt Blake, 38, a software engineer based in Oakland, Calif., was eager to grow his sailing experience during a recent trip to La Paz, Mexico, with his fiancée. He hired a captain but made clear that the captain was there to help and teach.

Where do you want to go?

“Do you want something that’s more culturally oriented? Nature oriented? An adventure trip?” asked Mary Curry, the voyage product director of Adventure Life , which offers small group tours and private trips on land and on water around the world.

That answer can determine your destination. Popular cruising grounds include the Caribbean, Croatia, Alaska and French Polynesia, but the sky — or the sea — is really the limit. For help narrowing your focus, travel advisers often have relationships with charter companies or outfits around the world, and sailing publications offer recommendations.

Kyla Malkani, who has had experience with charters working as a destination wedding planner, recommends consulting the concierge of waterfront hotels, particularly for short-term or day rentals.

“A lot of times they will have either their own fleet or they will have some sort of connection at a dock,” said Ms. Malkani, 37, who is based in Washington, D.C., and is currently working as a content creator and freelance event planner.

What kind of boat?

Where you want to travel and for how long will likely determine the kinds of boats that are available to you. Crucial at this point, too, is an understanding of the boat’s layout and amenities.

“You definitely want to choose the right kind of boat,” said Ms. Malkani. “If you want more adventure, a sailboat is nice. If you’re looking for a luxury party environment, a yacht is best. And if you’re looking for something smooth, for older people or with kids, a catamaran is great.”

David Barclay is a luxury travel adviser who has also chartered boats for his own vacations.

“You want to match what the travelers want to what the boat offers,” he said.

Perhaps a group of friends might not mind a catamaran with functional but not luxurious marine bathrooms, but a multigenerational group might prefer more high-touch amenities.

When should I book?

Often, charter trips are once-in-a-lifetime experiences that require a great deal of advanced planning.

“You may have a specific place you want to go, or a specific time of year you want to travel,” said Mr. Barclay. “And some places just aren’t good at certain times of year.”

Naturally, you don’t want to be at sea in the Caribbean during hurricane season, or in the Mediterranean during winter storms. But you also might want to avoid peak cruising seasons, too.

The first three weeks of August are quite popular, said Mr. Lockyer. “If you have some flexibility and can travel in early July, you’ll get the same sort of great weather, a greater selection of boats and the anchorages won’t be as crowded.”

How much does it cost?

Charter costs are incredibly variable, dependent on all of the factors coming into play: your boat type and size, your destination, your group size, the amount of crew you’d like and the amenities on board. That said, costs could range anywhere from $2,000 for a day on a sailboat to hundreds of thousands of dollars for a multiday mega-yacht charter. Have a budget in mind when beginning your research process.

What if I didn’t plan far in advance?

While advanced planning is encouraged, and often necessary for bigger boat trips, it’s possible to book a boat last-minute.

Boatsetter , an Airbnb-like platform for boats, is a good resource for last-minute bookings, especially for day trips, and even has an Instant Book option for down-to-the-wire bookings.

“If it’s for a special event, or around major holidays, you may want to book a month or two in advance. But for general bookings, you can find options within a week or two,” said Kim Koditek, Boatsetter’s head of brand strategy and communications, of the company’s overnight offerings, which appear on their platform under the luxury yacht charters category .

Ms. Malkani has used Boatsetter for some of her charters, most of which have been booked with a specific goal in mind.

“I’m a sunset chaser,” she said. “My husband and I just really love being on the water, and we always try to squeeze in some sort of boat day activity when we’re traveling.”

For more travel advice, visit our collection of Travel 101 tips and hacks.

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The First Annual Lenny Shabes Sailing Festival is in the Books

By: Zeke Quezada, ASA American Sailing Vacations , Flotillas

I strolled along the sandy shores of Anegada as a Caribbean squall swept over the island. The rain fell heavily, yet the sudden chill was oddly refreshing. The scene around me resembled something from a travel brochure.

Another American sailor who had joined us for the Lenny Shabes Sailing Festival flotilla approached me on the deserted beach. His floppy hat shielded his face from the downpour.

As we passed each other, he grinned. “It doesn’t get better than this.”

If there were words to capture the essence of this flotilla, it would be those simple yet profound words.

Sailing has a way of making any moment perfect. On that beach in Anegada, the entire journey seemed to find its definition.

Fourteen boats, 85 guests, and numerous islands to explore—this was what the Lenny Shabes Sailing Festival was all about. It celebrated sailing while honoring the legacy of ASA Founder Lenny Shabes. When a group of sailors gathers, you can imagine the tales spun over rum drinks. Whether on catamaran decks or sandy beaches, we all became part of the ASA Family in the British Virgin Islands.

The Raft Up

Our lead captain from the American Sailing School Sailing Virgins organized a sailor’s paradise—a raft where our boats formed a floating alley off Prickly Pear. The music blared, and swimmers danced inventively in the water. The jovial antics of sailors reached their peak as the Rum Runner arrived, elevating the energy on every boat and the water itself. Grills were fired up, flotation devices tossed into the water, and the biggest open-water pool party many of us had ever seen ensued.

The Regatta

Fifteen Hobie Cats set sail to compete in the inaugural Lenny Shabes Hobie Cat Regatta. While the winner was uncertain, everyone was too engrossed in the fun to mind the outcomes. Rumor had it the PhD in Meteorology took the race, but no sailor would admit to losing. The Bitter End Yacht Club hosted the race and a bonfire party that stretched into the night. Dinner, drinks, and dancing on the beach solidified friendships that felt lifelong after racing Hobie Cats together.

The Willy T

No trip to the British Virgin Islands is complete without a visit to the Willy T. People leaped off the back, singing and dancing as the day melted away. Our day began with a floating party aboard the lead American Sailing Catamaran and ended with farewells under a full moon, accompanied by a small glow party.

The Lenny Shabes Sailing Festival in the British Virgin Islands marked the first-ever celebration of American Sailing’s founder, Lenny Shabes. At its core, the festival embodied the spirit of sailing and camaraderie among sailors. It was more than just an event; it was a gathering of our sailing family, a heartfelt tribute to the sport we cherish, and a joyous celebration of the sea.

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Presidential yacht used by John F. Kennedy now available for charter

The legendary presidential yacht Honey Fitz has joined the charter market for the first time with Lessing's Hospitality Group.

Delivered in 1931, the 28.3-metre has been used by five US presidents: Harry S. Truman, Dwight D. Eisenhower, Lyndon B. Johnson, Richard M. Nixon and John F. Kennedy.

Honey Fitz was built by Defoe Boat & Motor Works in 1931 and originally owned by Montgomery Ward tycoon, Sewell Avery, who named her Lenore .

In time, the yacht took on the unofficial role of "presidential yacht". Honey Fitz was of special importance to Kennedy, however, who renamed her after his maternal grandfather John Francis Fitzgerald and cruised frequently with his family. First Lady Jacqueline Kennedy also redesigned the yacht's interiors in the early 1960s, which proved to be a passion of hers – she would later help curate the interiors of the 99.1-metre Christina O , owned by her second husband Aristotle Onassis.

In 2020, Honey Fitz underwent an extensive, historically sensitive restoration that saved her from "complete deterioration". Overseen by Charles R. Modica, the refit lasted three years with the yacht making her official reintroduction at the 2023 Palm Beach International Boat Show .

Honey Fitz can accommodate up to 35 passengers and features a main saloon, formal dining, a sundeck, a fully outfitted galley and a private owner's suite. Several functioning parts of the vessel date back to 1931, World War II and the presidential eras from 1945 to 1971, though the refit focused on the period during the Kennedy Administration.

Honey Fitz will be based at the Pelican Club in Florida and available for private charters alongside dockside events, including weddings and parties.

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