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Nearly 100 sleek-sailing yachts from throughout the Caribbean, the U.S. mainland and Europe plot a course for St. Thomas the last weekend in March. Their ambition? To compete in the International Rolex Regatta. Known far and wide as the "Crown Jewel of Caribbean Yacht Racing," this sailing contest boasts a unique blend of competition and island-style hospitality that offers fun for spectators and sailors alike.
It's nearly impossible to tell who's winning when watching a yacht race from sea or shore. That's because the diversity of yachts calls for a complex handicap system. Yet, the breathtaking beauty of so many vessels on the sea — everything from swift 60-plus-footers to lightning-fast Hobie cats — makes spectating popular. Especially picturesque are yachts flying huge sails, called spinnakers. Canvases of creativity and often mirrors of a sailor's sense of humor, spinnakers may be boldly colored — hot pink, neon yellow, lime green — or emblazoned with designs such as swooping eagles, brazen mermaids and smiley faces.
Rolex racing offers a mix of round-the-buoy and round-the island courses offshore. Viewing is best during the regatta's second day, when the fleet traces a spectacular route west along the island's south side into Charlotte Amalie's historic harbor. This is definitely the perfect vantage point to see the fleet up close and personal. The ideal way of watching is to bring a beach chair or blanket to sit on and find a spot along the waterfront bulkhead by 11 a.m. Not only do the yachts finish the day's first race here in the harbor, but they also start a second one that follows a course back east. This offers the opportunity to see helmsmen jockey their vessels for the best position along an invisible start line that runs from the committee boat to a buoy directly across from it. A class of like-sized yachts starts every five minutes. With a total of 10 or more classes, this means nearly an hour's worth of seat-of-the-pants yacht racing action right before your eyes.
Nightly parties hosted at the St. Thomas Yacht Club are open to the public. Beach barbecues, live music and the chance to schmooze with sailing's elite are the big draw. Of course, for the sailors themselves, the last night marks the pièce de résistance. True to tradition, each winner walks off with a fine Rolex timepiece.
Please check the Events calendar for exact dates and more info.
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