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Guide to the 7 best regattas in the Caribbean: A sailing enthusiast's dream


9 August, 2023


6 March, 2024

Blue waters, clear skies, consistent trade winds to fill your sails, and a lifestyle like no other, Caribbean regattas simply have to be experienced at least once in a lifetime. From superyachts to small boats, the calm waters of the Caribbean are even suitable for novice sailors. This is the place for those sunkissed adventures where dolphins dance around the prow, and you can drop anchor in a deserted cove to explore sugar-soft sands and coral reefs filled with colourful fish.

For sportsmen and women who take their sailing seriously, the Caribbean regatta schedule is a chance to push yourself and your vessel to the limits in fierce competition. And once the rosettes have been handed out, it’s time to enjoy the social side of Caribbean regattas, with fine dining, affluent villas and plenty to see and do.

There are several notable Caribbean sailing regattas every year that generate excitement and a competitive spirit among participants and spectators alike. The Caribbean regatta schedule 2024 includes some of the biggest events in the region.

To help you make the most of Caribbean regattas, we’ve put together this guide to seven of the best. Whether you’re taking part or simply love watching these fantastic vessels scudding across the blue waters of the Caribbean, at onefinestay, we have all the inside information you need to enjoy every second.

Round Barbados Sailing Week

Celebrating not just the competition but the culture, people, food and lifestyle of the Caribbean, the Round Barbados Sailing Week is a celebration of everything from tall ships to tiny yachts.

It’s the regatta that kicks off the season in the Caribbean and has been a part of island life since 1936. The first race involved five trading schooners who competed for ‘bragging rights’ and very little else. Since then, this major event in the Caribbean Regatta calendar has pulled in the crowds and competitors from around the world.

The 2024 regatta starts on Saturday 13th January with a weekend of dingy races, as well as surf and kiteboarding contests. This fabulous regatta ensures that anyone who enjoys being on the water feels included. The big offshore races start on Thursday 19th January and reach a climax with the Mount Gay Round Barbados Race on Sunday 21st January.

For the big offshore racing yachts, this competition is a challenging race that tests the skill and ability of sailors and their yachts to skim across the water. But the fact that this classic regatta is all-inclusive makes it a very special event. Book an elegant Barbados villa for the second week in January, and you can see why the Round Barbados Sailing Week is so special.

Grenada Sailing Week

The Grenada Sailing Week or Grenada Sailing Festival as it's also known, is one of the key Caribbean regattas.

It might all be about the sailing during the day, but once the yachts are moored up, the excitement and fun continue onshore with a real festival atmosphere. The festival started in 2012 and has gone from strength to strength since then. Today, it attracts the world's premier and Caribbean-based racing teams, such as the J/24 fleet.

What makes the Grenada Sailing Festival so popular? Well, it could be the picturesque sailing conditions, the constant trade winds that ensure top-class racing, the tranquil blue waters around the island, and the warm hospitality of the Grenadians. We like to think that it’s a combination of all of these elements, making this particular festival a not-to-be-missed event.

It's inclusive, fun, and guarantees sailing aficionados a fabulous week’s worth of competition in one of the most beautiful places on earth. You can catch this superb festival as part of the Caribbean sailing regatta schedule in the last week of January and the first week of February.

St Maarten Heineken Regatta

The Heineken Regatta St Maarten gives competitors and spectators alike the chance to discover this charming island's exceptional beauty and personality.

This is one of the top Caribbean superyacht regattas of the season, with some of the world's best racing teams taking part in intense competitions around the island.

Sponsored by one of the biggest breweries in the world, it draws in Olympic champions, Blue Ribbon competitors and round-the-world sailors. But don’t let that put you off if you’re a novice or intermediate sailor, as the St Maarten Heineken Regatta is a fully inclusive event that welcomes everyone with a series of Windward-Leeward events and coastal races for different levels of experience.

Once the racing is done for the day, everyone heads ashore for the evening celebrations and parties that continue well into the early morning hours. Expect to see top-level international acts entertaining the crowds before everyone grabs a few hour’s sleep. Then it’s back onto the water for some more racing. Book a villa on St Martin from the end of February to the first week in March to catch the races as part of the Caribbean regatta schedule 2024.

St Barths Bucket Regatta

Normally in a prestigious Caribbean regatta, you would expect the prize to reflect the level of skill of the participants.

But this is the Caribbean, and they certainly like to do things differently. So even though the St Barths Bucket Regatta is one of the most hotly anticipated events of the season, the prize for the main event is… a bucket!

That doesn’t stop the luxurious superyachts from making a beeline for this event. It’s been going for over 40 years and started life in Nantucket (hence the ‘Nantucket Bucket’, which just happened to be a spare bucket lying around that ended up as the first prize and is still presented today).

The action is thrilling, and the celebrations are typically exuberant in that refined Caribbean style typical of St Barts.

The St Barths Bucket is a highly prestigious event set against the backdrop of one of the most beautiful islands in the Caribbean. It’s a chance to experience the glitz and glamour of the upper echelons of the yachting fraternity and one of the best Caribbean regattas on the schedule. And all for a bucket…

Superyacht Challenge, Antigua

Held before the St Barth’s Bucket, the Superyacht Challenge Antigua is one of the most eagerly awaited and anticipated of all the superyacht regattas.

This is where the crowds come to see world-class 80+ foot yachts go prow to prow in four short sprint races of up to 30 miles.

Starting at English Harbour, these giants of the yachting world sail majestically around the coastline for the sheer pleasure of racing rather than to please any particular sponsors. That makes it a very special race that defines the true spirit of racing while thrilling the crowds that gather to watch the events.

This unique Caribbean regatta has a competitive spirit among the participants. Still, the relaxed and friendly atmosphere and the fact that there is no real 'prize' for winning makes it a very special event. It's typical of the Antiguan spirit, summing up that laid-back approach and passion for life.

Rolex Swan Cup Caribbean

Alternating between the Caribbean and the Mediterranean island of Sardinia, the Rolex Swan Cup is a competition that’s open to all Nautor’s Swan yachts.

This highly competitive bi-annual event is organised and sponsored by Rolex. With such a prestigious name associated with the event, you can imagine just how opulent this race is, attracting the best yachtsmen and women in this class from around the world.

Nautor's Swan yachts are the epitome of elegance and come in a wide selection of different classes, from the Swan, the Swan Maxi and the Club Swan to the Swan Shadow. If you're thinking of high-end yachts, you're probably thinking of a Swan.

It's no surprise, then, that such a high-profile brand as Rolex would be happy to associate with the maker of some of the finest yachts on the oceans, and that they would choose the Caribbean to celebrate the grace and elegance of these yachts in stunning locations. It's worth checking the Rolex Swan Cup site if you want to coincide your stay at a onefinestay dazzling Caribbean villa with this exceptional event.

Antigua Sailing Week

Not to be confused with the Antigua Superyacht Challenge, the Antigua Sailing Week is a classic Caribbean regatta that welcomes everyone of all abilities. This long-standing event has been drawing in sailing fans and competitors since 1967 and is regarded as one of the most vibrant, popular and exciting of all the Caribbean sailing events.

Five major races take place over a week, including the English Harbour Race. In the space of one week, over 5,000 spectators and participants discover the beauty of the waters off Antigua, making the most of the trade winds to create nail-bitingly exciting racing.

After the races, everyone heads to the Lay-Day Beach Party, an all-day event that includes dingy racing, games and BBQs on the beach. It’s a family-friendly affair that gives visitors a real insight into Caribbean culture and the laid-back approach to life that is such a part of the Antiguan character.

Enjoy the very best of the Caribbean regatta season

A fusion of sophisticated culture, sunkissed fun and some serious competition, the Caribbean regatta season is a wonderfully inclusive way to find out much more about the region and its heritage. Sailing has always played a key role in the culture of the Caribbean, and the regattas celebrate this every season.

If you’re planning on booking an exclusive Caribbean villa with onefinestay during the season, it’s worth reserving a little earlier than usual to ensure you get the pick of the best villas on offer. Many of our Caribbean villas are in prime beachfront locations, so you may even be able to watch the racing from the comfort of your sun lounger.

For keen sailors, nothing can compare to the Caribbean regattas. The camaraderie, the excitement and the thrill of racing in the Caribbean is the stuff of dreams. And who knows, you might even win a bucket! If you're interested in learning more about the Caribbean sailing scene, don't miss our comprehensive Caribbean sailing guide.

It's worth extending your stay to enjoy more than one of the Caribbean regattas, especially if you're a dedicated sailing fan. At onefinestay, your local concierge will be able to give you some local insights into the best spectator spots for the races and how to watch some of the most prestigious yacht racing in the world right here in the Caribbean.

With endless sunny days, gorgeous beaches, and a warm, friendly welcome, what more could you wish for?

Plan your sailing escape with onefinestay

With an array of superior villas in the Caribbean waiting to be discovered, onefinestay is your ticket to one of the world's most coveted destinations. Browse our destination guides to find out more or speak to our expert Travel Advisors who will match you with the dream Caribbean destination for your sailing adventure.