7 Top Winter Caribbean Sailing Regattas for 2017

Planning a winter holiday down in the Caribbean? Sailing regattas will add a touch of excitement (and maybe a little friendly competition) to your trip.

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The Mount Gay Rum Round Barbados Sailing Race (used with permission from The Barbados Cruising Club)

Sailing conditions are at their most ideal in the Caribbean from January through April, making it the perfect season for hosting some of the world’s finest regattas.

Spectators of Caribbean sailing regattas either love sailing and boats or can’t turn down a good party. Or both. That’s because, along with the thrilling rivalry of the races, there’s a spread of island events and celebrations (and rhum vanille) to enjoy.

The most popular caribbean sailing regattas for the winter season

In 2017, winter may technically end on March 19, but what’s considered the Caribbean’s high season doesn’t wrap up until April 14. Because of that, this list includes a few regattas that run into the early days of spring.

Mount Gay Rum Round Barbados Sailing Race (Jan. 16-24, 2017)

One of the oldest regattas in the Caribbean, the Mount Gay Rum Round Barbados Sailing Race will mark its 81st year in 2017. The prize is highly coveted — you can win your skipper’s weight in Mount Gay Extra Old. Mount Gay has produced rum on the island of Barbados since 1703. There are four full days of races, and you’ll find at least one party going on after every single one. If you can, get tickets to the Regatta Dinner held at The Beach House in St. James.

RORC Caribbean 600 Race (Feb. 19-24, 2017)

The RORC Caribbean 600 Race is relatively young, but it’s already attracting Olympians, America’s Cup sailors, and Volvo Ocean Race sailors. Spanning 600 miles and racing by 11 Caribbean islands, the RORC Caribbean 600 covers a lot of distance. Many of the big parties will be in Antigua, where the race starts and ends, but you’ll still find fun on any of the islands the ships race around, including St. Barths, St. Martin, Anguilla, Saba, and Nevis.

St. Maarten Heineken Regatta (March 2-5, 2017)

At last count, the four-day St. Maarten Heineken Regatta featured entries from over 37 different countries. When a regatta’s sponsor is a major beer company, you know that the accompanying parties will be interesting. There are concerts and parties every night, and in the past, this regatta has attracted performers like the Black-Eyed Peas, The Wailers, and Shaggy.

St. Barths Bucket (March 16-19, 2017)

The Bucket is an invitation-only Caribbean sailing regatta that features some of the most impressive mega yachts in the world. Even if you don’t watch the races, you can venture over to Gustavia Harbor after 5 p.m. most days to get a closer look at the participating vessels. There are celebrations galore during the Bucket — it’s the second biggest week in St. Barth after the famous New Year’s Eve festivities — and you’ll find viewing parties daily near the beaches and nightly parties at private villas or local restaurants.

St. Thomas International Regatta (March 24-26, 2017)

Along with the races, the Yacht Club has party bands every day starting at 4 p.m. There’s a complimentary breakfast, and meals served all day. It’s an easy way to enjoy a few days of competitive sailing and entertainment without having to island-hop or travel from location to location.

BVI Spring Regatta & Sailing Festival (March 27 – April 2, 2017)

The 46th annual BVI Spring Regatta combines all the most beautiful parts of the British Virgin Islands, including Virgin Gorda, Tortola, and Peter Island. It starts with two days of warm-up racing at Nanny Cay and then leads into three days of some of the Caribbean’s best racing. There are memorable parties everywhere, but don’t miss the fantastic fireworks show on the last night.

Les Voiles de St. Barth (April 10-15, 2017)

Les Voiles de St. Barth was created by two friends in 2010, and it’s quickly become one of the top Caribbean sailing regattas. The first year had 27 boats, but this year  no fewer than 80 boats and 1,000 sailors are expected. Of course, St. Barths always takes partying seriously, so you’ll find a designated race village at the Quai Général de Gaulle, in Gustavia, where the bar seems to be open all of the time. The daily prize giveaways are always a draw, as is the live music, fireworks, food, and killer cabaret show at Ti St Barth.

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You won’t have to travel far for Les Voiles de St. Barth or St. Barths Bucket the if you stay at Villa Gustavia Hill, also known as WV GUS.

Pencil in one of these Caribbean sailing regattas and secure your private villa reservation

The Caribbean sailing regattas listed above are all beloved and draw big crowds. If you’re planning to attend, book your villa with WIMCO  well in advance, so you have plenty of homes to choose from. Depending on the island you decide to visit, there may be several villas available that are only steps from the regatta festivities. Let your WIMCO Villa Specialist know you’re planning to attend the local regatta, and he or she will recommend the most appropriate villas.

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Have you ever attended a Caribbean sailing regatta? In your opinion, what is the absolute best regatta among all the islands? Share your thoughts in the comments below.