Miami Montego Bay
Pineapple
Cup Race
The next edition of the Pineapple Cup will start April 10, 2027.
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 2027 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.
MIAMI MONTEGO BAY PINEAPPLE CUP RACE SAIL ON JANUARY 25th, 2025 MIAMI MONTEGO BAY PINEAPPLE CUP RACE SAIL ON JANUARY 25th, 2025 MIAMI MONTEGO BAY PINEAPPLE CUP RACE SAIL ON JANUARY 25th, 2025 MIAMI MONTEGO BAY PINEAPPLE CUP RACE SAIL ON JANUARY 25th, 2025 MIAMI MONTEGO BAY PINEAPPLE CUP RACE SAIL ON JANUARY 25th, 2025 MIAMI MONTEGO BAY PINEAPPLE CUP RACE SAIL ON JANUARY 25th, 2025 MIAMI MONTEGO BAY PINEAPPLE CUP RACE SAIL ON JANUARY 25th, 2025 MIAMI MONTEGO BAY PINEAPPLE CUP RACE SAIL ON JANUARY 25th, 2025 MIAMI MONTEGO BAY PINEAPPLE CUP RACE SAIL ON JANUARY 25th, 2025
Race
Schedule
Skippers Meeting
April 9, 2027
Race Starts
April 10, 2027
Jamaica
Night
April 15, 2027
Awards Ceremony presented by MBYC
April 16, 2027
The Race Course to Montego Bay
Learn more & plan your 2027 race
Explore More
Latest News
2025 Pineapple Cup Cancelled
It is with great regret that the Montego Bay Yacht Club announce the unavoidable postponement of the
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
