Spectacle on the high seas: The best boat races in the Caribbean

by Melanie Reffes, From USA TODAY

Welcome to high season for boat racing in the Caribbean, where top-notch crews vie for top honors as they race their super-fast yachts and large sailboats in some of the most prestigious regattas in the world. As thrilling for spectators as it is for the competitive crews, cool parties after hot races are hosted by bars on the beach and seaside resorts. Check out our boat racing calendar and get ready to feel the wind in your sails.

St. Maarten
(Photo: Laurens Morel)
Named for the island and the sponsor, the St. Maarten Heineken Regatta started in 1980 with a modest 12 entries but today can boast that it is one of the largest sailing race in the Caribbean. Hosting 300 competitors from 32 countries, it’s all hands on deck for the world’s top sailors racing on the world’s fastest boats. From March 3 – 6, thousands of fans party hard at concerts staged on Kim Sha Beach and at après-racing parties, fueled by an endless supply of icy green bottles courtesy of the long-time title beer sponsor.

British Virgin Islands

Now in its 45th year, the regatta is a challenging 31 nautical mile competition with more than 100 international crews trying to break existing race records. (Photo: Cruising World)
Racing around Tortola; the largest island in the British Virgin chain and finishing at Nanny Cay on the south side between Road Town and West End, BVI Spring Regatta and Sailing Festival from March 28 – April 3 is the most-anticipated event of the season. Now in its 45th year, the regatta is a challenging 31 nautical mile competition with more than 100 international crews trying to break existing race records. Prizes up for grabs include dinner for a crew of 15, pricey bottles of bubbly and the all-important boating bragging rights. Hosted by the Nanny Cay Resort and Marina, Regatta Village is family-friendly for sailors and spectators who come to cheer on their favorite crew.

St. Barths

The invitational race started in 1995 with a fleet of four and today it is a hot ticket on the Caribbean regatta calendar featuring 39 of the world’s finest (and largest) super yachts charging for the finish line. (Photo: Tourism St. Barts)
Now in its third decade, St. Barths Bucket Regatta from March 17 – 20 is a three-day contest on the water with a crowd of top speed yachts all looking to take home the coveted Bucket Trophy. The race attracts the world’s most luxurious yachts — many approaching 200 feet in length — to the Port of Gustavia. The invitational race started in 1995 with a fleet of four and today it is a hot ticket on the Caribbean regatta calendar featuring 39 of the world’s finest (and largest) super yachts charging for the finish line.

Anguilla

Hosted by the Anguilla Sailing Association and Anguilla Tourist Board, Anguilla Regatta from May 6 – 8 is a race for glory that also raises money for the Youth Sailing Club. (Photo: anguilla-beaches.com)
Hosted by the Anguilla Sailing Association and Anguilla Tourist Board, Anguilla Regatta from May 6 Anguilla and neighbors Antigua, St. Maarten and St. Barths test their moxie on the water in spinnakers, mono-hulls and sailboats against the exhilarating, unpredictable wind shifts around the offshore cays. Now in its 14th year, races start at Sandy Ground with crowds waving on their favorite crew from vantage points on Crocus Bay, Prickly Pear, Rendezvous Bay and Meads Bay and restaurants and beach bars island-wide hosting après-race parties on the sand.

Antigua

For nearly half a century, English Harbour, Jolly Harbour, Dickenson Bay and Nelson’s Dockyard have been and continue to be spectacular sights with sport boats and racing yachts up to 100 feet in length bobbing on the waves. (Photo: allatsea.net)
Amongst the world’s premier racing events, Antigua Sailing Week is the granddaddy of Caribbean regattas. From April 23 – 29, races on the south coast attract 5,000 spectators and 1,500 participants from the Caribbean, Europe, North and South America, Australia and Japan competing in smaller contests like the Round Antigua Race and the Guadeloupe to Antigua Race on the Friday before the official racing begins. For nearly half a century, English Harbour, Jolly Harbour, Dickenson Bay and Nelson’s Dockyard have been and continue to be spectacular sights with sport boats and racing yachts up to 100 feet in length bobbing on the waves. For non-racers, shore-side partying and after-racing drinking is nonstop with special events that include the Beer Garden Party at the Antigua Yacht Club, breakfast at Shirley Heights Lookout and Champagne and Canapés at Catherine’s Cafe Plage. For families who like racing, Dockyard Day at Nelson’s Dockyard wraps up with the awards ceremony with a performance by the Royal Antigua and Barbuda Police Band.

St. Kitts and Nevis

On the final day, ‘Booby Island Cup‘ is a spirited race around Booby Island and its challenging rocky shoreline. (Photo: SceneKitts)
Named for the small, uninhabited island halfway between St. Kitts and Nevis, Booby Island Regatta and Sailing Festival from April 30 – May 2 is the big ticket for racers and non-racers who come for three days of fun on the water and parties on the beach. Kicking off with the fan-favorite called the ‘Chase the Monkey’ that starts at White House Bay in St. Kitts, the winner is crowned at Cades Bay in Nevis with chartered party boats taking fans to watch the winner cross the finish line at Chrishi Beach. On May 1, crowds gather early to cheer on the yachts racing in the ‘Round de Rock’ from Paradise Beach to Charlestown; the capital city of Nevis. On the final day, ‘Booby Island Cup‘ is a spirited race around Booby Island and its challenging rocky shoreline. Plenty of hooch on the high seas and after-race beach parties keep the fun going until the early hours.

Barbados

Named for and sponsored by the largest supermarket chain on Barbados, Massy Stores Dinghy Regatta is an elegant race organized by the Barbados Yacht Club. (Photo: Peter Marshall)
Held on two Sundays — May 22 and June 26 — races in several categories are geared to sailors with experience on the high seas and also to younger sailors up to 15 years old. Races light up the water on the crescent shaped Carlisle Bay on the southwest coast of Barbados, where shifting winds challenge even the most seasoned sailors. Spectators gather at the Esplanade, south of Bridgetown, for views of the cruise ships to the north and the yachts competing in the natural harbor.

For more on this story go to: http://experience.usatoday.com/beach/story/best-of-caribbean/2016/02/18/best-famous-boat-races-caribbean/80258178/