Pineapple Cup Race
Montego Bay, Jamaica
- Website: http://www.pineapplecup.com/
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.