History of the race
It all started in 1961
It all started in 1961 and has continually run every other year since...
One of the oldest offshore races on the calendar, The Pineapple Cup – Montego Bay Race started in 1961, making 2025 the 36th edition of the venerable 811 nautical mile race. Immediately after the start, teams 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.
Pineapple Cup Course Record
Argo a Mod70 broke the outright course record in 2019 with an elapsed time of 2 days 7 minutes and 44 seconds.
Past Champions
Monohull Elapsed Time Records
Year
Boat Name
Skipper Name
Elapsed Time
2005
Titan 12
Tom Hill
2:10:24:42
2003
Zephyrus V
Robert McNeil
2:23:05:57
1971
Windward Passage
R. Mark Johnson
3:03:40:07
1969
Windward Passage
R. Mark Johnson
4:10:22:29
1963
Bolero
Sally A. Langmuir
5:11:29:27
1961
Escapade Baldwin
M. Baldwin
7:01:08:36
Multihull Elapsed Time Records
Year
Boat Name
Skipper Name
Elapsed Time
2019
Argo
Jason Carroll
2:07:44:00
2003
Zephyrus V
Robert McNeil
2:23:05:57
- 1961, Escapade, Baldwin M. Baldwin
- 1963, Guinevere, George M. Moffett
- 1965, Ticonderoga, Robert E. Johnson
- 1967, Vamoose, R.E. (Ted) Turner
- 1969, Flyway, Ogden R. Reid
- 1971, Improbable, David W. Allen
- 1973, Lightnin, R.E. (Ted) Turner
- 1975, Kialoa, John B. Kilroy
- 1977, Kialoa, John B. Kilroy
- 1979, Tenacious, R.E. (Ted) Turner
- 1983, Condor, Robert Bell
- 1984, Cachasa, Mike Gruener
- 1985, Stormy Petrel, Blaine Nashold
- 1986, Sassy, Russell Sahmrda
- 1987, Scaramouche of Warwick, Arthur Bugs Baer
- 1988, Saucy Sue, Lt. Cdr. Hardly Lewin, Jamaica Def. Force
- 1989, Commodore Rucanor, Bruno Dubois
- 1990, Saucy Sue, Lt. Cdr. Richard Russell, Jamaica Def. Force
- 1991, Merry Thought, Jack King
- 1992, Challenge America, Patrick O'Callaghan
- 1993, Pipe Dream, Dr. Scott Piper
- 1995, Dear Friend, Bill Kardash
- 1997, Dear Friend, Bill Kardash
- 1999, Critical Path, William (Bill) R. Dooley
- 2001, Bonkers, Bill Zartler
- 2003, Zephyrus V, Robert McNeil
- 2005, Thin Ice, Stuart Hebb
- 2007, Carinthia, Frank Kern
- 2009, Privateer,Ron O'Hanley
- 2011, Genuine Risk, Hugo Stenbeck
- 2013, Shockwave, George Sakellaris
- 2015, Shockwave, George Sakellaris
- 2017, Prospector, Paul McDowell, Larry Landry and David Siwicki
-
2019, Lady Mariposa, Nigel King
2023, Callisto, Kate and Jim Murray
