caribbean yacht racing calendar

2024 Caribbean Regattas

Barbados Sailing Week

Grenada Sailing Week

RORC Caribbean 600

Heineken St. Maarten

St. Thomas [STIR]

BVI Spring Regatta

Les Voiles de St. Barth

Antigua Sailing Week

Antigua to Bermuda Race

You can sail in all of the most prestigious sailing events in the 2024 Caribbean Regattas Calend ar   with Ondeck including   Barbados Race Week ,  Grenada Sailing Week ,  RORC Caribbean 600 ,  St Maarten Heineken Regatta ,  St Thomas International  , BVI Spring Regatta ,  Les Voiles de St Barth , Antigua Sailing Week and the Antigua to Bermuda Race which will be making a come back for 2024 . We also have places at some of the smaller fun events such as Nelsons Pursuit Race and Round the Island Antigua.

Our Farr 65, Spirit of Juno , regularly achieves podium finishes and is very competitive in class. She is our 'head boat'  so generally available for individuals or small groups to join the team and our professional crew. She is also available to book whole boat.

We also have  a Beneteau First 36.7 available for whole boat charter with brand new sails

Ondeck can cater for everyone from experienced race crews wanting a whole yacht bareboat to individual travelers looking to join a team and experience the camaraderie of actually taking part in a major sporting event

There is nothing to surpass the thrill of competitive, high-performance yacht racing in crystal clear waters with consistent warm trade winds. If you haven't succumbed to the pull yet let us help you decide.

Our dedicated shore support and maintenance crew work around the clock to ensure your needs are met, they all understand the challenges faced by racing yachts and racing crews.

Click on the events above for full details of charter dates and prices and individual places. If you have any questions, just EMAIL [email protected] or call the Antigua office. 1 268 562 6696

Most of our race packages include 1 training day with the option of taking part in deliveries from and back to Antigua where applicable and building some miles.

In particular the Antigua - Barbados - Grenada - Antigua circuit adds 1100 nautical miles and 2 regattas to your experience within 3 weeks.

For booking, please click on the ' Regatta Dates & booking ' button on the right or ' Contact us! ' for more information.

Official websites

C aribbean 600 RORC 

St Maarten Heineken

St Thomas [STIR]

BVI Spring Regatta 

Les Voiles d St Barths

Nelsons Pursuit Race Antigua

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The outlook for the Caribbean’s 2022 winter and spring regatta season is sunny and bright. That’s great news after protocols and precautions to protect against the COVID 19 pandemic led to the cancellation of most major regattas from the BVI to Grenada for the last two years, and the St. Thomas International Regatta for one as organizers were able to hold the event in 2021. Here’s a preview of what to expect:

THE OUTLOOK

There are 12 major Caribbean regattas scheduled from January through May 2022, according to the Caribbean Sailing Association’s (CSA) Caribbean Regatta Circuit Calendar. As of late November, there have been no cancellations, regatta organizers have planning underway and some of the hottest racing yachts in the Caribbean and World are already entered.  

“We are very optimistic about racing in the Caribbean in the spring. From a global perspective, travel has resumed, and we know competitors are eager to return and experience the magic of racing here,” says Laura Muma, spokesperson for Les Voiles de St. Barth Richard Mille , April 17-23, 2022, in St. Barths. “We are also thrilled to be included as a featured event for the International Maxi Association’s (IMA) new Caribbean Maxi Challenge, open to all Maxis above 60 feet.”

The IMA’s first Caribbean Series includes four regattas: the RORC Caribbean 600 (February 21), St. Maarten Heineken Regatta (March 3-6), Les Voiles de St Barths Richard Mille, and Antigua Sailing Week (April 30-May 6).  

Likewise, “We are very confident about the 2022 edition and the return of the Bucket is well underway with planning and preparations in full swing,” says Jeanne Kleene, event manager for the St. Barths Bucket , March 17-20, 2022. “The big boat regattas in the Med this year, coupled with the 5 superyacht regattas that have taken place beginning in June, reinforce that belief. As many people expressed during the pandemic, there is now a pent-up demand, and our superyacht owners, captains, and crew are eager to get back into action.”

The Corinthian Spirit initiative returns to the 2022 Bucket, with new class rules accepting both spinnaker non-spinnaker entries. Organizers will also offer a 90-foot Class.

THE INTEREST

With record entries for the ARC (Atlantic Rally for Cruisers) and RORC Transatlantic, the number of sailing boats in the region will be impressive, according to Michele Korteweg, general manager of the St. Maarten Yacht Club and CSA president. “Many already indicated an interest in the St. Maarten Heineken Regatta, including several Polish teams returning to defend their titles from 2020 and previous years. Many of them have chartered Volvo 60s and 70s including I Love Poland, who got first place in their class in 2020. On a regional and local level, we are happy to welcome the Melges 32 fleet back and there are 2 DIAM 24s that will participate. Hopefully, we will attract another Diam 24s already in the region to start a one-design class. This is something we are looking forward to growing as they are great boats with lots of potential and are easily shipped.”

There were 59 official entries for Antigua Sailing Week (ASW) by the end of November. “This is more than double the number for this period relative to 3 years ago,” says Rana Jamila-Lewis, events and marketing manager. “We have strong UK interest followed by Germany and we expect to see an increase in American entries after the holidays. Overall, very positive from the local market as well with much of the Antigua flagged previous participants already committed to taking part.

For the first time in 2022, ASW will host a dedicated women’s race day to recognize female skippers and participants. There will also be a new sport boat class, which has been in development since 2020.

Interest is picking up from international sailors wanting to visit Barbados to participate in Barbados Sailing Week, January 18-23, says Renata Goodridge, organizer, CSA Measurer, and member of the Barbados Sailing Association. “As of November 2021, the Blue Peter and Spirit of Juno from Antigua are confirmed, and six other positive enquiries. We are also excited to have kiteboarding as a class for 2022, so there will be lots of action.”

A few highlights of entries as of late November for Les Voiles de St. Barth Richard Mille are the USA’s Wendy Schmidt’s new Botin 85 Deep Blue, the USA’s Jim Swartz’s 72-foot Maxi Vesper, and an impressive number of beautiful Swan yachts ranging from 58- to 80-feet.

Over a dozen yachts were registered as of November for the 48th St. Thomas International Regatta (March 25-27, 2022) and the 49th BVI Spring Regatta and Sailing Festival (March 28-April 3).  

“We have condensed the race week to allow visiting boats a few extra days to sail before the Sailing Festival begins March 30th,” says Judy Petz, director of the BVI regatta. “The Sailing Festival starts with the Scrub Island Invitational Regatta, a fun race taking the fleet to the eastern islands, such as Virgin Gorda, before arriving at Scrub Island Resort and Marina. Racing will continue the next morning with a race towards the BVI western island group. This new format allows for an abundance of informal racing, a view of the different islands of the BVI, and acts as a warm-up to the main event that kicks off April 1.”

Ten boats from the Caribbean, Europe, and the USA were entered for the Caribbean Multihull Challenge (February 4-6) as of November. These include the USA’s Greg Slyngstad’s Bieker 53, Fujin, and USA’s Todd Slyngstad’s HH66, Nemo.

“This is the kind of year that it is hard to know numbers ahead. Unlike in the past, bookings may come late,” says Steve Burzon, one of the regatta organizers. “On the windiest day of the three of the event, we will present a 60 nautical mile course starting in Simpson Bay, and heading upwind to St. Barth’s, then turning north toward the French island of Tintamarre, and then a downwind race in the famed Anguilla Channel and back to Simpson Bay. This 60-mile course is open to any CMC registered yacht that can complete the entire course in under six hours. This is going to be fun for the Ocean Racing and Carbon Fiber lightweight cruisers.”

THE NEW NORMAL

The new normal for Caribbean regattas will be a strong and continued focus on great racing offshore.

“Social events may have to be curtailed a little, but our focus will be the sailing/racing side of things so that probably won’t affect us too much,” says Ginny Field, press officer for the Antigua Classic Yacht Regatta, March 30-April 4, 2022.

Similarly, the St. Maarten Heineken Regatta’s Korteweg adds, “Onshore entertainment is still being reviewed, however big concerts are currently not being considered. Light entertainment, (daily) prize giving and an after-sailing happy hour seem more feasible, all depending on the COVID situation closer to the time. This means that the St. Maarten Heineken Regatta concept will be adjusted to fit within the current pandemic situation, focused on offering world-class sailing.”

For a calendar of Caribbean regattas, visit: https://caribbean-sailing.com/calendars/international-regatta-5-year-calendar/ For links to Regatta COVID Updates, visit: https://caribbean-sailing.com/regatta-covid-updates/  

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Antigua Sailing Week

Well over 100 yachts participate each year, ranging in size from 24 feet to over 100 feet. The Regatta attracts all types of yachts from serious racing boats including state-of-the-art, high-tech racing machines to a variety of performance cruising and cruising boats and even features a Club Class for less serious racers who want to be part of the on-the-water action.

The sight of all these yachts is unforgettable, both from vantage points on the shore and from spectator boats carrying onlookers alongside the races. The reputation of Antigua Sailing Week allows the event to attract some of the world’s top racing and performance cruising boats and some of the most famous professional sailors in the world.  You don’t need to own a personal yacht as it’s easy to ‘Rock up and Race’ with one of many available race charter outfits.  If the highly competitive race class isn’t what you are looking for, luxurious bareboats can be booked through  Sunsail Moorings and Dream Yacht Charter.

For five days crews are challenged with a variety of coastal race courses encouraging tacking duels around the buoys – all in the picture-perfect setting of the deep blue Caribbean Sea off Antigua’s south coast with the ever-present trade winds. The idyllic racing is enhanced by sailors retiring to Antigua Yacht Club for passionate post-race analysis and daily prize-givings which carry on into the evening. Hundreds of locals and visitors will continue partying well into the late hours but yacht crews know there is another day of racing so they leave the late night revelry for the others to finish.

After the week of ever-exciting racing, Antigua Sailing Week draws to a close in the romantic historic Nelson’s Dockyard with the final awards presentation attended by owners, skippers and crews, with their friends, well-wishers and race officials, alongside Antigua’s government representatives including the Governor General to present the awards.

This exciting event is followed the next day by Dockyard Day and the Beating of the Retreat as the Antiguan flag is lowered to signal the close of Antigua Sailing Week for yet another year.  It is a truly fitting end to a week of glorious racing.

The Notice of Race, Sailing Instructions and other official documents can be found on Yachtscoring,com.

To enter Antigua Sailing Week 2024 click here.

This Class is open to sailors who want to participate in the on-the-water action but who may not take their racing as seriously as others and don’t want to incur all the usual expenses. If you are racing to win, this is not the class for you!

• The entry fee is US $9 per foot of measured overall length.
• Acceptance of entries into the Club Class is solely at the discretion of the Organising Authority. High performance boats, boats using high tech sails or spars, boats that have previously done well under CSA racing or boats with highly trained crews will not be accepted into the Club Class.
• The Class will be scored using Variable Simplified CSA Handicap. Boats that already have full CSA Ratings may enter the Class but will still be issued a CSA Simplified Rating, at no cost. Boats without a CSA Rating must request a CSA Simplified Rating at a cost of US $50 by accessing this link . All boats should endeavor to have their Simplified CSA Handicap a few days BEFORE the close of registration.
• Boats may enter as jib and main (pole or no pole) only or with spinnakers.
• After each day’s racing, individual ratings will be adjusted up or down according to the following formula: New Rating = Old Rating X Equalizing Factor X Reward Factor . Yachts that do well (better than 4th place) will have their rating adjusted up while yachts that do not do as well (worse than 4 th place) will have their rating adjusted down. The newly adjusted rating becomes your rating for next day’s race. This will result in tighter racing as the week progresses with more opportunities for all teams to experience the thrill of a podium position. Equalizing Factor : Calculated as the ratio of each finisher’s corrected time to the 4th place boat corrected time to a minimum and maximum amount of 0.950 to 1.050, inclusive. Performance Reward Factor : This does not vary for the duration of the regatta. 1 st = .990, 2 nd = .994, 3 rd = .997, 4 th = 1.000, 5 th = 1.003, 6 th = 1.006, 7 th = 1.010, 8 th = 1.011, 9 th = 1.012, 10 th = 1.013, 11 th = 1.014, 12 th and below = 1.015 If the boat has no finish time (DNC, DNS, DNF, etc), then New Rating = Old Rating . For the top three finishers, the New Rating will not be less than the Old Rating. For finishers below fourth place, the New Rating will not be more than the Old Rating.
• All class participants must accept the Variable Simplified CSA Handicap procedures.
• The CSA Simplified Rating or the Variable Simplified CSA Handicap procedures are not subject to competitor protest.
• There will be one race per day for the Class with no throw-outs.
• Courses will be 2-3 hours long with less emphasis on windward/leeward performance in as much as that is possible within our geographic and mark placement limitations.
• Club Class entries will not be eligible for The Royal Southern Yacht Club Challenge.
• This list of rules is NOT final. Please check back for possible updates.

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How to win the RORC Caribbean 600: Expert’s guide

• February 15, 2024

World and European Championship-winning professional navigator Tom Cheney talks through the challenges of the RORC Caribbean 600 course

Inaugurated in 2009, the RORC Caribbean 600 is a relatively recent addition to the calendar of 600-mile offshore yacht races, adding to the list of established bluewater classics like the Rolex Fastnet and Sydney Hobart races. Its route, around 11 of the Leeward Islands in the Caribbean, is one of the most navigationally challenging of the 600-milers.

Starting and finishing in Antigua, the race’s 12-leg, figure-eight type route stretches from St Martin in the north to Guadeloupe in the south, weaving a Caribbean course that is as stunning as it is demanding.

The consistent north-easterly tradewinds and the looping nature of the course will exercise every sail in the wardrobe, and rewards boats set up for performance on all points of sail. There is far more fetching and reaching in this race than in a typical Fastnet or Sydney Hobart, for example. The sheer number of legs and sail changes are also a great challenge for crews and navigators alike.

The Caribbean 600 Route

Caribbean 600 start

The starting line is off Fort Charlotte on the rugged coast of Antigua at the eastern entrance to English Harbour, above the Pillars of Hercules and below Shirley Heights. The first part of the race is an eight-mile beat to Green Island, the easternmost point of Antigua. While the Caribbean 600 doesn’t usually attract as many entries as a race like the Rolex Fastnet, this first leg can still be very hectic, as boats battle for the convergence on the left under cliffs and headlands. There are a couple of rocks to look out for here, a particularly noteworthy one at Standfast Point, although this is well charted.

Comanche at the start of the RORC Caribbean 600 in 2022 – the race often attracts a mix of local, charter and visiting yachts. Photo: Arthur Daniel/RORC

From Green Island you can sail the rhumbline to the inflatable rounding mark off Barbuda while paying attention to the Antiguan reefs. In big seas this might not be the case, and you may want to give the lee shore some more room. Usually this leg is around 090° TWA, but it’s risky to try to set reaching sails too early on this leg as there is very little runway to leeward for the first seven miles.

Anticipate the wind dropping and lifting you as you approach Barbuda. You will likely be VMG running by the time you reach the mark and may even have to gybe.

Barbuda to Nevis

This is usually a long (50-mile) downwind VMG leg. There is a wind shadow in the lee of Antigua, which is often indicated by a long cloud street. Once through the wind shadow, the wind will likely be 10° to the right of the gradient as the breeze wraps around the island, this is a nice header on port if you time the gybe well. It will likely be the evening of day one by the time most of the 40-footers are at Nevis.

Nevis to Saba

This leg is another 50-mile leg, broad reaching behind Nevis and St Kitts. Nevis is particularly tall and there are lots of land effects as you sail in the lee of the islands and the funnelling channels between them. Once again the wind bends as you approach the shadow of Nevis and St Kitts – you will likely hang onto a spinnaker for longer than you initially expect.

Saba is also tall and there is a two-mile leg to sail up very close to its western shore. Watch out for dive buoys and be ready to be in wind-seeking mode when in the worst of the wind shadow. Getting too far from the island will be punishing as the next leg will be proper upwind VMG.

There are rocks and outlying islands to avoid when rounding St Barths

Saba to St Barths

Rounding the north of Saba, the wind first bends right around the island – so there is a small gain by taking a hitch in to get the lift – then it becomes a header as you sail back into the gradient breeze. Often this leg is one of the lumpier upwinds, if this is the case then a good strategy is to get to the left into more sheltered waters on the shelf in the lee of St Barths.

St Barths to St Martin

The smaller boats should benefit from doing this next leg in daylight – useful as there are plenty of rocks and outlying islands to avoid. Slower boats also need to keep a lookout for the faster boats on a reciprocal course, having already rounded the top mark.

Tom Cheney and the Sunrise team competing in the 2022 RORC Caribbean 600

The first rocks, Les Grenadiers, are steep sided, so you can get close to them. A header around Les Grenadiers often makes you feel like you won’t be able to lay Ile Toc Vers, but as you get offshore, the wind will likely lift, so don’t worry if you are initially low of the layline.

Don’t rely on the charted positioning of Roche Table (Roche Plate). It is steep sided though, and visible, so you can get very close to it once you’re confident of its position. Pay attention to Les Roches Rouges: there’s an uncharted shallow spot at 17°50’.6N, 062°50’.6W.

St Martin to Tintamarre

From the westernmost corner of St Martin you are back to upwind VMG towards Tintamarre. There is significant foul wind-driven current offshore. Before you get lifted, get back inshore, otherwise it’ll be hard to get back. There are some good gains to be had short tacking inshore, making the most of wind bends on the headlands, although there’s a risk it could be light and flukey in places.

Be aware of Spaniard Rock between Eastern Point and Tintamarre. It is possible to get inside Spaniard Rock for some sea state relief and possibly a tiny lift around Tintamarre.

A long wind shadow is found in the lee of Guadaloupe

Tintamarre to Guadeloupe

This is the longest leg of the course, 150 miles, from Tintamarre and St Barths down to Guadeloupe avoiding Montserrat.

The initial part of the leg from Ile Tintamarre to St Barths is always tighter than you think and is almost hard on the wind. The current does seem to change direction here, so keep an eye on course to steer and keep COG-ing at the mark. Try not to get low of rhumbline, sail the shortest distance and anticipate being headed around St Barths.

St Barths to Guadeloupe also ends up tighter than everyone expects, often 60°-70° TWA. There is a decision as to which side to pass of Montserrat. The shortest course is to stay to the east of it. Don’t get too close to the windward side of Montserrat, as there can be a bit of a windward bubble.

The wind shadow of Guadeloupe is often the most challenging part of this race. Time of day has a big effect on how soft the conditions are, but many boats arriving during the night get becalmed for hours. There is a high resolution WRF GRIB forecast available that models the size of the shadow well, although it can sometimes be optimistic about wind strength.

The 70ft trimaran Maserati flying into the finish – the final stage is usually upwind from Redonda to Antigua. Photo: Arthur Daniel/RORC

Pick a point as a target and aim for it, eg Pointe Des Peres. Getting half to one mile off the beach has been the winning option for most races. There’s no point getting a long way offshore, because all this distance will be ground to sail upwind again later. It’s also unwise to end up in a no man’s land around two miles offshore. Stay pretty close and there’s a good chance of drainage breeze through the night. If you do get stuck in no wind, just push south, as that’s the quickest route back to the breeze and to the next mark.

After the long reach to Guadeloupe you’ll head up and beat to Les Désirade, leaving Iles de Saintes to port. There are some tricky bits to this leg including a rock off Grand Ilet and an exclusion zone around Terre de Bas. There is often a large wind speed increase at the bottom of Guadeloupe.

People are normally tired by this point and it’s a hard beat. There are also lots of lobster pots. Désirade is a bit hairy and has lots of rocks, so give it a good safety margin.

Les Désirade to Barbuda

After Les Désirade there is another long reach at approx 100° TWA. It will help that you’ve already found the inflatable at Barbuda once before, particularly as it may be getting dark when you get to it the second time. This is usually a fast leg but a good one for a navigator to get some rest. It can be a little demoralising sailing past Antigua, finish in sight, but with 115 miles of race left to go.

The leg to Redonda is often a broad reach but can be downwind – if so make the final 10 miles on port layline for cleaner air. Photo: RORC/Tim Wright

Barbuda to Redonda

Likely a gybe set at the mark, the leg to Redonda should be a fairly simple broad reach. Be a little wary of getting into the wind shadow of Antigua. As before, this should be signposted by a long cloud street. If this leg is more of a downwind than a reach, it’s best to do the final 10 miles on the port layline.

Redonda to Antigua

The final 34 miles upwind to the finish should be a fairly square beat. Once again the wind shadow of Antigua comes into play and this could be a final opportunity to get some leverage by picking the correct side of the beat. If the wind is left, then stay further offshore and sail up the south side of the clouds. If the TWD is right, then a rule of thumb is to get left to benefit from the starboard lift on the edge of the Antigua wind shadow and flatter sea state.

At the very end there are gains to be had inshore, but stay outside the reefs. There are nice lifts coming out of Curtain Bluff and another out of Rendezvous Bay, but you need to get right onto the beach to get the left-handers.

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Navigating the 2024 Caribbean Sailing Circuit: a journey through paradise

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2024 Programme of Events

As you prepare for the 2024 RORC Caribbean 600 and RORC Nelson's Cup Series, please add the following dates to your diary.

Pre-event, please contact the RORC Race Team, Cowes on +44 (0)1983 295 144

From Monday 12th February, our on-site team will be available in the Antigua Yacht Club Regatta Office between the hours of 1000-1700 local time. 

Download the Event Programme here.  Event Programme 2024.pdf

Preliminary Schedule of Events

The 2024 st barths bucket: 21-24 march 2024.

Updated 11 March 2024

2024 Preliminary Racing Schedule

Note: ‘ BMQ ’ is the Bucket Marquee on the Quay; ‘ Collectivite ‘ is across the harbor.

2024 Preliminary Social Schedule

The organizing authority and race committee reserve the right to modify the above schedule depending on weather conditions or other unforeseen circumstances.

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by AYC | Jan 15, 2024 | AYC News , Latest News , Notice of Race

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by AYC | Jan 9, 2024 | AYC News , Latest News

Notice Of Race – AYC Mini Dinghy Regatta – Sunday 14th January – Registration is Open

by AYC | Jan 3, 2024 | AYC News , Latest News , Notice of Race

Nelson’s Pursuit Race – 31st Dec – Registration Open

by AYC | Dec 27, 2023 | AYC News , Latest News , Notice of Race , Sailing Instructions

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by AYC | Dec 14, 2023 | AYC News , Latest News

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by AYC | Dec 1, 2023 | AYC News , Latest News , Social Events

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by AYC | Nov 22, 2023 | AYC News , Latest News

Notice of Race – The BUDGET MARINE Jolyon Byerley Series

by AYC | Nov 15, 2023 | AYC News , Latest News , Notice of Race

Antigua Wins the Nations Cup – 2023 Caribbean Dinghy Championships in Martinque.

by AYC | Nov 2, 2023 | AYC News , Latest News , Race Results

by AYC | Nov 2, 2023 | AYC News , In Memoriam , Latest News

Mini Regatta Report, Results & Photos

by AYC | Sep 19, 2023 | AYC News , Latest News , Race Results

Bart’s Bash 10th Event hosted by Antigua Yacht Club & National Sailing Academy

by AYC | Sep 19, 2023 | AYC News , Latest News , Youth Sailors

Mini Regatta & Barts Bash – Sunday 17th September

by AYC | Sep 12, 2023 | AYC News , Latest News , Notice of Race

Registrations Open Summer Sailing Program – Full Schedule Here

by AYC | Jun 26, 2023 | AYC News , Latest News , Semester Program

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Caribbean Yacht Racing

Caribbean regatta season – a ‘must do’ for competitive sailors.

Pure sunshine, warm breezes, and mesmerising blue water racing and cruising, paired with Caribbean style partying on offer, you can definitely see why the Caribbean is so popular as a winter retreat.  The main Caribbean race season runs from January to late April avoiding the hurricane season.

With a great selection of regattas in the Caribbean, there is a race to suit everyone. Open to all levels, world class events, good food and live music, the Caribbean has it all!

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Find below a selection of our yachts currently available to charter in the Caribbean. Click on their individual pages to see which races they are available for. If a particular boat doesn’t have a race listed, or an event doesn’t have a boat you would like to charter, please contact us to see how we can assist.

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SW105 – Wolfhound

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Browse which yachts we have available specifically for each event by selecting an event. If you have something in mind that isn’t displayed please contact us as it may be something we can source, or isn’t currently listed.

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The top superyacht regattas to add to your 2024 calendar

Related articles.

From the South of France to St Barths, the superyacht regatta calendar is packed with opportunities for owners to race their boats in stunning settings. Whether you are looking for keen competition or are more interested in the après scene, we are here to help you pick the perfect contest.

Oyster World Rally, Antigua

From 14 january, 2024 .

By the finish of the 22/23 rally, more than 100 Oysters had circumnavigated over the decade that the British builder has been running these rallies. Dozens more will have their chance at the next one, which heads west from Antigua and makes 15 stopovers on the 16-month route.

New Zealand Millennium Cup, Auckland

February 23-26, 2024.

Postponed from 2023, the Millennium Cup 2024 takes place in a new location – Auckland, aka the City of Sails, which eases logistics for international owners. There is also a new multihull division as well. What isn’t changing is the fun racing with a Kiwi flavour.

Superyacht Challenge, Antigua

March 11-17, 2024.

Defining superyachts as vessels over 24.4 metres, this regatta offers four days of lively racing from the entrance to English Harbour as well as relaxed parties brimming with camaraderie in historic Nelson’s Dockyard.

The race is held annually in Nelson’s Dockyard and comprises daily pursuit races, and an optional race around the island, with the start and finish line just off English Harbour. Entrants are divided into three classes — buccaneers, corsairs and privateers — and all compete under the ORC Superyacht Rule.

Rather than a traditional trophy, winners receive barrels of rum, suitably filled in true Caribbean style. Additional awards include best-dressed crew, loudest Caribbean shirt, and a cook-off between crews. In fact, the only trophy awarded is the Gosnell Trophy, which is given to the crew that has "competed in the Spirit of the Regatta" both on the water and ashore.

St Barths Bucket Regatta

March 21-24, 2024.

The St Barths Bucket Regatta attracts some of the finest sailors and sailing yachts from across the world and is always a highlight on the racing calendar. This invitation-only event welcomes around 40 superyachts (usually upwards of 30 metres in length) to the sandy shores of St Barths each year.

The racing has traditionally been on three courses but organisers have said they now have 30 options to choose from.

Off the water, owners have their choice of countless invitations, from private gatherings to the Bucket-affiliated soiree at Tamarin as well as the final awards ceremony party, which is traditionally held at the five-star Eden Rock hotel. At the yacht hop, some owners have been known to fly in thousands of oysters and host aerial silk performers, which proves that the old Bucket spirit of winning the party — if not the day on the water — is still prevalent.

The 2024 fleet is already shaping up nicely with regatta regulars such as the 56-metre Malek , 51-metre Red Dragon and 35-metre Whisper all making a return, with the new 59-metre Maximus also anticipated to join. 

Les Voiles de St Barths Richard Mille

April 14-20, 2024.

A relative newcomer to the racing scene, Les Voiles de St Barths may not be steeped in history like many long-timers on this list, but it has swiftly become a calendar staple since its inception in 2010. It welcomes a serious fleet of modified racers and mini maxis - think TP52s and JV72s - among smaller racing boats and a multihull fleet.

Now in its 13th year, the event will see the fleet return to the red-roofed town of Gustavia in St Barths. Like the bucket, the regatta is powered by reliable trade winds that arrive from the east, which means very few days are lost due to unfavourable weather conditions. Racecourses make use of the landscape with clusters of rocks punching out of the water that serve as marks. Some more competitive teams even send divers down to see how close they can get before having to tack off.

Racing is close and competitive but things are much more laid back ashore. The lay day usually consists of a long lunch at Nikki Beach followed by tug of war and diving for bottles of Barons de Rothschild champagne.

Giorgio Armani Superyacht Regatta

June 4-8, 2024.

The Sardinian superyacht regatta is back as the Yacht Club Costa Smeralda welcomes Giorgio Armani as its title sponsor for the second year.

Where other regattas may have a T-shirts and flip-flops feel, Sardinia is about glamour in the playground of the Italian elite. It’s not all focused on the nightlife, though; any serious sailor knows racing here is not for the faint-hearted.

“Sardinia is, in my eyes, the most exceptional regatta area in the world,” says the owner of  WinWin . And he's not wrong. Competitors can expect stronger winds from the northwest and have to navigate rocks jutting out of the water in Bomb Alley — the passage between Sardinia and La Maddalena archipelago.

The regatta is always capped off with an evening at Phi Beach —  WinWin ’s owner says it’s the best party of any regatta. It’s a quintessentially Italian summer scene, with guests treated to glorious sunset views and music from top DJs piped through bars and dance floors interspersed among the rocks right on the water.

Entry is open to superyachts with a minimum length of 27.43 metres and the event will also encompass the Southern Wind Rendezvous.

Superyacht Cup, Palma

June 19-22, 2024.

This annual event for yachts over 24 metres is the longest-running superyacht regatta in Europe, and now incorporates a Corinthian Spirit Class

A laid-back southern Mediterranean vibe prevails at the Superyacht Cup in Palma, Europe’s longest-running superyacht regatta. Leave your jackets and ties at home; this is a shorts and T-shirt event. Uniquely, this regatta is contained within a fenced-in event village, proving that relaxed and informal can also mean ultra-exclusive.

While racing in the Bay of Palma may not offer the same dramatic scenery as the Caribbean, it is ideal for newcomers who may find rounding inflatable marks less daunting than a rocky outcrop, and its more sheltered position means there are no boat-breaking big seas. The race committee has the ability to set courses in the bay to suit the fleet and to really give every yacht a better chance to sail to its rating.

Last year's fixture welcomes a quartet of J Class entries, Svea , Topaz , Ranger and Velsheda .

Maxi Yacht Rolex Cup

September 8-14,  2024.

The Maxi Yacht Rolex Cup is the highlight of many a Maxi racing calendar and is back for its 34th edition in 2024. Staged off Sardinia’s Costa Smeralda - known for its rocky scenery and turquoise waters – it continues to attract dedicated owners, highly skilled crews and exceptional yachts. 

This year's Cup follows a hugely successful event last year. Racing is open to yachts of at least 18.29 metres and, for the first time this year, multihulls can join its ranks.

Oyster Palma Regatta, Palma

September 21–25, 2024 .

Taking place at the new venue of Port Adriano, this special edition celebrates 50 years of Oyster Yachts. In addition to the friendly competition over four days of racing, there will be an owners’ dinner to commemorate its half-century of building bluewater cruising yachts.

Ibiza JoySail, Balearic Islands

September 19-22, 2024.

Now in its fourth edition and growing exponentially each year, this laid-back regatta welcomes maxis and superyachts for offshore and coastal racing in the Balearic Islands, along with plenty of onshore socialising hosted by STP Palma and Marina Ibiza.

Les Voiles de St Tropez

September 26 – 6 october, 2024.

The Mediterranean big-boat racing season winds down with Les Voiles de Saint-Tropez. But don't be fooled, this is no small soirée. The event is the largest gathering of Maxis yachts in the world as owners and crew come together and toast to the last of the summer sun with a week of good old-fashioned racing. 

Swan Med Regatta-Tuscany Challenge, Marina di Scarlino, Italy

October 2024 .

New to the calendar last year, the inaugural Tuscany Challenge gathered Med-based Swan owners for a first ever Med-based end-of-season regatta set against the stunning backdrop of the Tuscan archipelago. This Nautor Swan Experience gathering celebrates the entire Swan world across a three-day competition. Hosted by the Yacht Club Isole di Toscana, it determines the world champions in the ClubSwan 50, ClubSwan 42 and ClubSwan 36.

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