The Top Caribbean Regattas

CTO UK Chapter

Feel your sails straining in fresh trade winds, spray dousing the crew as you accelerate under a full canopy in glorious sunshine. Ah, the thrill of regatta racing. Sailors enter in their hundreds, attracted by the prospect of winning start lines, executing smooth mark roundings and perfecting manoeuvres under the pressure of competition.  Add a drop of Caribbean spice for a potent cocktail of close racing, legendary parties and sublime weather.

Find out why Antigua Sailing Week, the St Martin Heineken Regatta and the BVI Spring Regatta are some of the most fun and exciting racing events in the international sailing calendar, and how they can form the perfect backdrop your Caribbean holiday. Get involved in the festival fever, whether you’re planning to enter or not.

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Antigua Sailing Week – April 29th to May 5th 2017

Getting ready to celebrate an incredible half century at the end of this month means the latest edition of Antigua Sailing Week is set to be even more special than usual.

Founded in 1968 by a group of sailing hoteliers trying to persuade people to stay or arrive in Antigua a little later into the season, they stumbled on a formula that has seen little change since inception, with a proven combination of thrilling yacht racing by day and fabled beach parties by night.

Over 100 yachts will take part in the regatta, with many arriving specifically for the event from elsewhere. Planning a visit to the island around Sailing Week is a fool proof recipe for finding fun things to see and do, as the whole island comes to life to celebrate its love of sailing.

The series of races span various classes, and range in length and layout, such as; Antigua to Guadeloupe, Round Antigua Race Day, Antigua to Bermuda, and the south coast three day series. Spectators are able to watch at least part of most races from vantage points around the island, or even pay for a place aboard a racing or spectator boat that ‘chases the race’.

Every night when the sun goes down, the rum will flow at both the official sponsored parties and the impromptu hangouts around the fleets and across the island.

Outside of the regatta and during the lay day, you can explore one of Antigua’s 365 beaches or make sure to catch a steel band dance session. For those looking for a little solitude, neighbouring Barbuda boasts pink coral sands, brilliant reefs for swimming and snorkelling, and plenty of opportunities for superb bird watching.

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St Martin Heineken Regatta – March 2nd to March 4th  2018

Celebrating its 38th anniversary in 2018 and operating under the motto “serious fun!”. The Heineken Regatta makes the most of the area’s prevailing north easterly trade winds, average temperatures of 25C and clear blue waters.

Over 37 nationalities were represented at the 2017 edition, making it a truly international event. The regatta attracts around 2,500 sailors and 1,000 spectators, with hundreds of yachts of all shapes and sizes taking part.

Big names from the world of music are regularly attracted to parties on both the Dutch and French sides of the island, and so the evening scene sets out to rival any summertime music festival.

Outside the regatta, you’ll find that St Martin is a hotspot for discerning celebrities, drawn to its buzzing nightlife, casinos and chic boutiques. Those who are comfortable in and on the water can also visit neighbouring Anguilla for secluded beaches and shipwreck diving excursions.

BVI Spring Regatta – March 26th – April 1st 2018

The 47th edition of this regatta will take place next year and there is no reason to think that it won’t continue to be as popular as ever.

Largely down to wide appeal of the British Virgin Islands as whole for both sailors and non-sailors alike and, 2016 saw 84 entries from all over the world, including quite a few who used Sunsail boats to reach podium positions in various racing classes. The racing is incredibly varied, encompassing the Round Tortola Race for the Nanny Cay Cup, and the Scrub Island Invitational.

The evening party scene centres around the Nanny Cay resort, the events main sponsor. But it’s hard to put a foot wrong on wherever you may decide to go in the British Virgin Islands. From the Soggy Dollar Bar and Foxy’s restaurant on Jost Van Dyke, to snorkelling at the Indians or cave exploration at the Baths on Virgin Gorda, there is something for everyone here. Not to mention the BVI’s most extraordinary feature, Anegada, a coral atoll some 14 miles north of the main island of Tortola where those in search of some quiet time will find miles of beautiful beaches with plenty of space.

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The RORC Caribbean 600 – Monday 19 February 2018

For the hardy offshore racers among you, The Royal Ocean Racing Club holds a spectacular 600nm bi-annual race around the Leeward Islands. Starting out from English Harbour, Antigua, the Caribbean 600 course winds around St Kitts & Nevis, Saint Eustatius, Saba, St Barths, St Martin, Montserrat and Guadeloupe, before finishing off back in Antigua. Not for the faint-hearted, this non-stop, week-long racing adventure takes your standard long distance ocean passage, and adds a tropical twist, with shorts and t shirt weather, fresh breezes and thousands of coral islands whizzing by under a fierce sun. Oh, and the party on arrival in Antigua is nothing short of legendary.  A must for most serious sailors’ wishlists. You can absorb the race’s atmosphere with a cruise out to the start and finish lines from our base in English Harbour.

Get your race face on

Now you have the lowdown on the best regattas around, why not join the action? You can find out more at, and charter a yacht for the Antigua Sailing Week, Heineken and BVI Spring regattas on 03303321620.

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