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

2017-06-30T08:34:43-05:00 en-US Jun 30, 2017

By: Melanie Reffes

Source: USA Today

Welcome to 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.

Anguilla

Photo: Anguilla Boat Racing, Source: Anguilla Tourist Board

It’s biggest party of the year on the small island across the sea from St. Martin, and the busiest time of the year for boat racing. For 12 days (Aug. 2 - 13) Anguilla’s Summer Festival is the hot ticket for soca raves, calypso concerts, parades, pageants, the wildly popular August Monday J'ouvert blowout beach party that starts at 5 a.m. and continues through the next morning, and schooner races that honor the island’s national sport. Dating back to the early 1900s when the first organized race marked the end of World War I, boat racing is a time-honored tradition and a sight to behold for fans of the sport. The Super Bowl of races, Champion of Champions on Aug. 13 is the most important on the calendar. Thousands of die-hard fans line the sun-baked shores as the boats with giant white sails take to the high sea.

Grenada

Photo: Grenada Sailing Week, Credit: Tim Wright Photo Action 2016, Source: Grenada Sailing Week

One of the prettiest races in the Caribbean, Carriacou Regatta on Grenada’s little sister isle is a watery wonderland Aug. 4 - 7, when crews from around the world show off their work boats, sailboats and yachts. Also a good bet for landlubbers, the three-day summer party invites with a roster of fun stuff like donkey racing and beauty pageants. For sailing fans who like to plan ahead, Grenada Sailing Week from Jan. 29 to Feb. 3 is all about spiffy boats, spirited skippers and fans snapping photos from the beach.

Aruba

Photo: Aruba International Regatta, Credit: Joost Howard, Source: USA Today

Three days of parties and two days of racing mark the Aruba International Regatta, Aug. 18 - 20. At Surfside Beach close to the airport in the capital city of Oranjestad, the summer sailing fete features races on yachts, beach cats and sunfishes and plenty of beach barbecues, concerts on the sand, windsurfing competitions and all-day happy hours.

British Virgin Islands

Photo: 2018 Race Routes, Source: BVI Spring Regatta

One of the longest-running races on the Royal BVI Yacht Club calendar, Willy T Virgin’s Cup, or the Virgin's Race as many call it, is also one of the more unique in the Caribbean. Slated for Oct. 21, rules stipulate that all boats entered must have a female skipper. 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 26 to April 1 is the most-anticipated event of the season. Now in its 46th year, the seven-day regatta is a challenging 31-nautical-mile competition with more than 150 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.

Barbados

Photo: Mount Gay Round Barbados Race 2017, Credit: Peter Marshall, Source: Round Barbados

First held in 1936 when five trading schooners competed for bragging rights and small prizes, Mount Gay Round Barbados Race is one of the most anticipated of the racing season. Organised by the Barbados Cruising Club in association with Mount Gay Rum and Barbados Tourism Marketing Inc., the 70-mile race around the island gets underway on Jan. 16 and continues through Jan. 24. While most boats sail for the honor of the fastest time, the consolation prize of a barrel of Mount Gay Rum for the slowest time was discontinued after two boats remained out at sea for days stalling to take the prize. Today, there are no prizes for coming in last, although trophies for the fastest boats are highly coveted.

St. Maarten

Photo: Party Shot, Source: Heineken Regatta

Named for the island and the sponsor, St. Maarten Heineken Regatta started in 1980 with a modest 12 entries but today can boast that it is one of the largest sailing races in the Caribbean. Hosting 300 competitors from 36 countries, it’s all hands on deck for the world’s top sailors racing on the world's fastest boats. From March 1 to 4, thousands of fans party hard at beach concerts and at après-racing parties, fueled by an endless supply of icy green bottles courtesy of the long-time beer sponsor.

St. Barths

Photo: 2017 St Barths Bucket Regatta, Credit: Claire Matches, Source: Bucket Regatta

Now in its third decade, St. Barths Bucket Regatta (March 15-18) is a three-day contest on the water with a crowd of top-speed yachts all looking to take home the 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 circuit, featuring the world’s finest (and largest) super yachts charging for the finish line.

Antigua

Photo: 50th Antigua Sailing Week, Credit: Paul Wyeth, Source: Antigua Sailing Week

Among the world’s premier racing events, Antigua Sailing Week is the granddaddy of Caribbean regattas. From April 28 to May 5, 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. For half a century, English Harbour, Jolly Harbour, Dickenson Bay and Nelson’s Dockyard are the places to be to see 100 racing yachts measuring up to 100 feet in length. For non-racers, shore-side partying and after-racing drinking is non-stop, with special events that include beer parties at the Antigua Yacht Club and breakfast at Shirley Heights Lookout. For families who like racing, charter a spectator yacht for up-close views of the action.

About the Author

Melanie Reffes, Travel Journalist
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