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

Latest News:

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

April 4 / 2016

Pineapple Cup 2017 Announced 
The iconic ocean race returns February 3, 2017. Read More HERE


Pineapple Cup

Fort Lauderdale - Montego Bay

February 3, 2017

Miami - Montego Bay

811 nautical miles

​Monohulls and Multihulls



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.   


​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!