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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.


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.


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…