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2019 Pineapple Cup NOR Released. Entries are now OPEN!

2019 Pineapple Cup Dates Announced!

The 2019 Pineapple Cup will start on Sunday, January 27th and will be followed by the Cuba Cup. Race entry and the Pineapple Cup Notice of Race can be found here!

About the Pineapple Cup:

The Pineapple Cup – Montego Bay Race is endorsed by the Jamaican Tourist Board and managed by Montego Bay Yacht Club and Manuka Sports Event Management. 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.  

Click HERE for more photos

The Pineapple Cup & Cuba Cup are produced in association with the following organizations: 

Latest News:

February 27 / 2017

Amhas wins the inaugural Cuba Cup! Read more HERE.


February 11 / 2017

​Winners of the 2017 Pineapple Cup celebrated at awards dinner! Read more HERE.


February 8 / 2017

Senara sixth boat to cross finish line in PHRF fleet. Read more HERE.

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2019 WESTERN CARIBBEAN SERIES

Pineapple Cup

Miami - Montego Bay


January 27, 2019

Miami - Montego Bay

811 nautical miles

​Monohulls and Multihulls