Event· Montego Bay· Other Caribbean

Pineapple Cup (Miami to Montego Bay Race)

18° 27.7′ N · 77° 56.5′ W · approximate

One of the oldest offshore races in the Caribbean: 811 nautical miles from Miami across the Gulf Stream, down the eastern side of the Bahamas toward the tip of Cuba, and on to the Montego Bay Yacht Club. Ted Turner won it three times.

Practical

Coordinate approximate (the finish host, Montego Bay Yacht Club). First run in 1961 and normally every other year; the 2025 race was postponed. Next edition: skippers' meeting April 9, 2027; start April 10, 2027; Jamaica Night April 15; awards at MBYC April 18, 2027 (pineapplecup.com). Expect the club's docks and anchorage to be busy around the finish.

Best for

Racing or partying at the finish in Montego Bay