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    Antigua Defends Nations Cup Title for Seventh Year as Caribbean Dinghy Championship Marks 30th Edition in Sint Maarten

    Antigua Defends Nations Cup Title for Seventh Year as Caribbean Dinghy Championship Marks 30th Edition in Sint Maarten

    Anegada:  Cow Bones, Shipwrecks & Lobster at Sunset

    The New CSA Majors Trophy – A Grand Finale

    Team TTO Competes in Sint Maarten at the 2026 Caribbean Dinghy Championships

    Team TTO Competes in Sint Maarten at the 2026 Caribbean Dinghy Championships

    Anegada:  Cow Bones, Shipwrecks & Lobster at Sunset

    Registration Opens for the West Indies Regatta Festival 2027

    2026 Caribbean Dinghy Championship Returns to Sint Maarten for 30th Edition

    2026 Caribbean Dinghy Championship Returns to Sint Maarten for 30th Edition

    St. Vincent and the Grenadines Sends Largest-Ever Team to Caribbean Dinghy Championships

    St. Vincent and the Grenadines Sends Largest-Ever Team to Caribbean Dinghy Championships

    Anegada:  Cow Bones, Shipwrecks & Lobster at Sunset

    Salty Dawg Departures Scheduled from Florida, Bermuda

    2026 ARC and ARC+ Fleets Gather in Gran Canaria for Atlantic Crossings to the Caribbean

    2026 ARC and ARC+ Fleets Gather in Gran Canaria for Atlantic Crossings to the Caribbean

    2026 St. Barth Cata Cup Draws 42 Teams for 18th Edition

    2026 St. Barth Cata Cup Draws 42 Teams for 18th Edition

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    Antigua Defends Nations Cup Title for Seventh Year as Caribbean Dinghy Championship Marks 30th Edition in Sint Maarten

    Antigua Defends Nations Cup Title for Seventh Year as Caribbean Dinghy Championship Marks 30th Edition in Sint Maarten

    Anegada:  Cow Bones, Shipwrecks & Lobster at Sunset

    The New CSA Majors Trophy – A Grand Finale

    Team TTO Competes in Sint Maarten at the 2026 Caribbean Dinghy Championships

    Team TTO Competes in Sint Maarten at the 2026 Caribbean Dinghy Championships

    Anegada:  Cow Bones, Shipwrecks & Lobster at Sunset

    Registration Opens for the West Indies Regatta Festival 2027

    2026 Caribbean Dinghy Championship Returns to Sint Maarten for 30th Edition

    2026 Caribbean Dinghy Championship Returns to Sint Maarten for 30th Edition

    St. Vincent and the Grenadines Sends Largest-Ever Team to Caribbean Dinghy Championships

    St. Vincent and the Grenadines Sends Largest-Ever Team to Caribbean Dinghy Championships

    Anegada:  Cow Bones, Shipwrecks & Lobster at Sunset

    Salty Dawg Departures Scheduled from Florida, Bermuda

    2026 ARC and ARC+ Fleets Gather in Gran Canaria for Atlantic Crossings to the Caribbean

    2026 ARC and ARC+ Fleets Gather in Gran Canaria for Atlantic Crossings to the Caribbean

    2026 St. Barth Cata Cup Draws 42 Teams for 18th Edition

    2026 St. Barth Cata Cup Draws 42 Teams for 18th Edition

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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 & Rallies
Reading Time: 2 mins read
A A

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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