Miami Montego Bay
Pineapple
Cup Race 2025
The 2025 Pineapple Cup sets sail on January 25th, 2025
The Race
It all started in 1961 and has continually run every other year since...
One of the oldest offshore races on the calendar, The Pineapple Cup – Montego Bay Race started in 1961, making 2025 the 36th 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.
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Race
Schedule
Skippers Meeting
Friday January 24, 2025
Race Starts
January 25 & 26, 2025
Jamaica
JNight
January 30, 2025
Awards Ceremony presented by MBYC
February 1, 2025
The Race Course to Montego Bay
Start Your Sailing Journey Now
Latest News
Callisto wins Pineapple Cup!
Callisto wins the 35th Pineapple Cup – Montego Bay Race! The Silver perpetual trophy was
Rikki Finishes Pineapple Cup
At 08:00:51 on Thursday, January 26, the Rhode Island based team Rikki crossed the Appleton
Callisto Arrives into Montego Bay
At 21:21:07 on Wednesday, January 25th, Callisto Racing was second across the Appleton Estate Finish
Pyewacket70 captures line honors!
Pyewacket70 captures line honors in the 35th Pineapple Cup – Montego Bay Race Pyewacket70 finishes
