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SAVE THE DATE: JANUARY 22-29, 2022

811 nautical miles Miami to Montego Bay

One of the oldest offshore races on the calendar, The Pineapple Cup – Montego Bay Race started in 1961, making 2021 the 35th edition of the venerable 811 nautical mile race. Immediately after the start, 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.

LATEST NEWS

February 6, 2026

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Designed like a half-marathon/full-marathon pairing, the two races are distinct but sailed together. Tower Race competitors will sail the traditional 48-mile course, while Salty 100 teams will complete the same course twice, adding a second lap for an extended offshore challenge.

January 7, 2026

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Starting Friday, May 22, 2026 — A Premier Ocean Racing Event on the New England Sailing Calendar kicks off another huge year

December 17, 2025

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This article offers a clear explanation of how the ORC system works, how it uses data to generate fair handicaps, why design limits sometimes become necessary, and how ORC continually updates the rule to stay aligned with modern yacht design.

In Partnership with:

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NOTICE BOARD

VIA YACHT SCORING

NOTICE OF RACE & REGISTRATION FOR 2020 WILL BE POSTED SOON!

ABOUT THE EVENT


Proud Partnership with Montego Bay Yacht Club

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A Bi Annual Event

Storm Trysail Club is happy to support this biannual event by supporting the starting line in Miami with a Race Committee. Many past Storm Trysail Members

EVENT LOGISITCS


For more logistics information visit PineappleCup.com

REGISTRATION

Registration is done via Yacht Scoring before the event.

ELIGIBILITY

IRC rated boat with 30 feet minimum. PHRF with a LOA of 30 ft and 150 rating. Multihulls at least 30 feet.

RACING

The course to be sailed shall be from a Start line in the vicinity of Government Cut, Miami, through the Bahamas Islands to the finish line off Montego Bay, Jamaica.

AWARDS

At the Awards, there are many Trophies including a favorite: THE JAMAICA TOURIST BOARD LOG AWARD for the

most interesting log, to be determined at the discretion of the Montego Bay Yacht Club Race Committee.