History of the race

It all started in 1961

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 2017 the 33rd 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.

Pineapple Cup Course Record

Argo a Mod70 broke the course record in 2019 with an elapsed time of 2 days 7 minutes and 44 seconds.
Argo sailed a distance of 869nm at an average speed of 18.05 knots.

Past Champions

Discover the illustrious history of champions who have left an indelible mark on the competition. From thrilling victories to unforgettable moments, these past champions have etched their names in the annals of Pineapple Cup.

Monohull Elapsed Time Records

Year
Boat Name
Skipper Name
Elapsed Time

2005

Titan 12

Tom Hill

2:10:24:42

2003

Zephyrus V

Robert McNeil

2:23:05:57

1971

Windward Passage

R. Mark Johnson

3:03:40:07

1969

Windward Passage

R. Mark Johnson

4:10:22:29

1963

Bolero

Sally A. Langmuir

5:11:29:27

1961

Escapade Baldwin

M. Baldwin

7:01:08:36

Multihull Elapsed Time Records

Year
Boat Name
Skipper Name
Elapsed Time

2005

Titan 12

Tom Hill

2:10:24:42

2003

Zephyrus V

Robert McNeil

2:23:05:57

2023 Pineapple Cup Teams

Argo a Mod70 broke the course record in 2019 with an elapsed time of 2 days 7 minutes and 44 seconds.

Pyewacket 70 🇺🇸

Volvo70

Callisto 🇺🇸

Pac52

Rikki 🇺🇸

R/P 42

Weather Routing Inc. is Proud to be a Weather Provider for the Pineapple Cup Montego Bay Race Click the logo above to access weather forecast data for the Pineapple Cup race course.

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