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
March 11, 2026
The slides, recording, and recap for the webinar are now available.
February 19, 2026
The Storm Trysail Club’s Intercollegiate Offshore Regatta Series (IORS) continues its national growth in 2026 with three premier events spanning the country
February 6, 2026
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.
In Partnership with:
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
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
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.