Skinny Sailing

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 clubhouse for weigh-in, I am impressed to see scores of volunteers diligently making last-minute preparations as a warm breeze fills the open-air clubhouse.

Our moment of truth comes as our last crewmember clocks in to give us a crew weight of 838 pounds—safe! Given that the forecast called for lighter-than-average winds, this feels like a good thing.

Twenty-four hours later, however, those 12 pounds are sorely missed as Red Dog, Williams’s IC24—a modified J/24 and the Caribbean’s most competitive class—bashes into 18 knots of wind and steep 3-foot seas near the starting area. “There’s another drink you owe me, Tyler!” exclaims Olin Davis, our bowman, as an errant wave soaks the foredeck. While the water might be warm here, Davis and Max Nickbarg—our spinnaker trimmer—expect great results and a dry ride from their skipper.

Rice nails the pin-favored downwind start of the Town Race as Davis and Nickbarg pop the kite exactly on cue. We settle into 6 miles of sleigh ride along the island’s southeast coastline to Charlotte Amalie as Nickbarg and Williams keep the sails powered up. Rice keeps the wind indicator pegged due astern as we surf down the stubby seas. Despite our efforts, we can’t shake the competition: the entire fleet is sprinting within a few boat lengths of each other, with minimal passing opportunities. Even as we enter our first mark rounding, miles later, there’s virtually no separation.

The race committee divides the first day into three longer races—the downhill sprint to Charlotte Amalie, followed by two upwind races back to the yacht club—each of which features unusual course shapes, and uses the coastline and the surrounding smaller islands to create challenges and opportunities, especially on the close-winded legs.

“OK guys, we’re sailing windward-leewards today,” announces Rice as we sail to Great Bay, which is northeast of the yacht club, for the start of day two’s racing. “The race committee wants to get in eight races today.”

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