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Callisto starts the race.

Callisto starts the race.

Callisto Wins Pineapple Cup 2023

Caribbean Compass by Caribbean Compass
March 16, 2023
in REGATTAS
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Jim and Kate Murray’s Callisto has won this year’s Pineapple Cup — the biennial race from Florida to Jamaica. The Doyle-powered Pac52 enjoyed champagne sailing conditions. Doyle Sails expert Justin Ferris, who sailed with the crew, reports that there were “near perfect sailing conditions, warm water and a near perfect training run for Callisto for the lead up to the RORC Caribbean 600 Race. We were treated to exceptional downwind sailing conditions from windward passage to the finish line, 16-25 knots of wind and big waves as we neared the finish. This year’s Pineapple Cup has to be one of the most enjoyable races I’ve done in years, and we really need to take our hats off to the race organizers and sponsors for sticking it out as the fleet numbers dropped. Jim and Kate Murray set a goal to keep it fun, basing the team around sailing buddies.”

Their plan has paid off, as the mostly non-pro team has won three races in a row.

The winning team

One of the oldest offshore races on the calendar, The Pineapple Cup — Montego Bay Race started in 1961. The 811 nautical mile race starts in Miami, and racers cross the Gulf Stream for the Northwest Providence Channel. The middle of the race offers a fetch down the eastern side of the Bahamas Island chain toward the tip of Cuba. The final stretch is typically a sailor’s dream: a 240-mile downwind sleigh ride from Cuba’s eastern tip, known as the Windward Passage, to the finish at Montego Bay.

Jim Murray describes his favorite moment: “There was a gorgeous crescent coming into Montego Bay and we had these large waves from the stern and it was gusting 24 knots and we just were absolutely hauling the mail downwind and the whole crew was actually pretty silent. It was everyone just doing their jobs, and after three days on the water that’s why you do this, because everyone just loves being part of the team.”

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