top of page


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 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.

Pineapple Cup

Course Record

Argo a Mod70 broke the course record in 2019 with an elapsed time of 2 days 7 minutes and 44 seconds.


Argo sailed a distance of 869nm at an average speed of 18.05 knots. 


Elapsed Time Records


Elapsed Time Records

Past Champions

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

*The Pineapple Cup Perpetual Trophy is awarded to the IRC boat with the best corrected time.

  • White Facebook Icon
  • White Instagram Icon
bottom of page