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



Click the link below to download the NOR and register for the

2017 Pineapple Cup & Cuba Cup

The Pineapple Cup Returns!

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.   

The Pineapple Cup & Cuba Cup are sponsored by:


Latest News:

December 5 / 2016

Quantum announced as official Sailmaker of the Pineapple Cup and Cuba Cup! Read More HERE

November 17 / 2016

Announcing Bainbridge, AirX, Karver and Plastimo as Partners for the Pineapple and Cuba Cups! Read More HERE

August 16 / 2016

Winter Escape 2017! 5 great races that fit together for a great winter sailing schedule! Read More HERE

May 16 / 2016

NEW Western Caribbean Series Announced: Pineapple Cup & Cuba Cup. Read More HERE

​Cuba Cup

Montego Bay- Havana

February 17, 2017

Montego Bay - Havana

640 Nautical Miles

Monohulls and Multihulls 

Winter escape 2017


Sailing in the Sun, Easy Schedule, Tropical Locations, Historic Races

Plan your escape now!

Pineapple Cup

Miami - Montego Bay

February 3, 2017

Miami - Montego Bay

811 nautical miles

​Monohulls and Multihulls