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

Pineapple Cup

Miami - Montego Bay

January 27, 2019

Miami - Montego Bay

811 nautical miles

​Monohulls and Multihulls



2019 Pineapple Cup & Cuba Cup NOR coming soon!

2019 Pineapple Cup and Cuba Cup Dates Announced!

The 2019 Pineapple Cup will start on Sunday, January 27th and will be followed by the Cuba Cup. More details to follow shortly!

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

​Cuba Cup

Montego Bay- Havana

February 2019

Montego Bay - 24° 27' 30" N

640 Nautical Miles

Monohulls and Multihulls 



race trakcer


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.