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Thus begins a time of hunger, but the trade-off is compelling: 10 days of sacrifice for the serious fun of sailing in a legendary Caribbean event with a group of dialed-in high-school sailors and the boat’s skilled and gracious owner, Mike Williams.The 37th annual St. Thomas Rolex International Regatta sees 66 boats racing in seven classes to compete for four Rolex timepieces. Walking into

The powerful Caribbean sun drums down on the racecourse, whose flat, island-protected seas are combed by a 12-knot breeze. The starting line is short, and as Rice executes a great boat-end start, I spot the windward mark, maybe a mile to weather. An offset leg, perhaps three boatlengths long, and a leeward gate are the only other course features. It’s obvious that while yesterday’s racing was interesting and scenic, today is dedicated to thoroughly grilling each crew. Here, one tactical error, a bungled maneuver or a missed windshift tests preparation and concentration: the fleet is full of serious inter-island sailing talent and recoveries are virtually nonexistent. We return to the dock that evening exhausted and sun-baked.

By day three, sunburns and chapped lips are taxing the 65 or so IC24 sailors as we amble over to Nazareth Bay and the start of the first race. The race committee wastes no time striking up the starting line samba. We’re soon rifling through beats, sets and drops in an animated blur of staccato-style sprints, this time on a racecourse that’s punctuated by sloppy seas and land-influenced wind shifts.

The biggest challenge—besides staving off the fleet’s heavy hitters—is keeping pace with the race committee’s schedule, as energy and attention spans begin to lapse. After 17 races, there’s no doubt that Puerto Rico’s Fraito Lugo (Orion) earned his Rolex —which he gave to his trimmer, Milton Gonzalez—or that the race committee gave sailors in all seven classes a full-value racing experience.

Staggering up the dock, wasted from weight loss, an overdose of vitamin D and so much sailing, I realize that it’s the mark of a great regatta when a cold beer, a comfortable chair and shade become life’s biggest desires. And perhaps a real meal…but only after reliving the weekend’s excitement with friends ashore.

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