From 1961-1990 the Pineapple Cup ran from Miami to Montego Bay. From 1991-2015, the race start was moved to Ft. Lauderdale. The 2017 race will return to the original start location in Miami.

1961EscapadeBaldwin M. Baldwin
1963
GuinevereGeorge M. Moffett
1965Ticonderoga
Robert E. Johnson
1967VamooseR.E. (Ted) Turner
1969Flyway
Ogden R. Reid
1971Improbable
David W. Allen
1973Lightnin
R.E. (Ted) Turner
1975Kiaola
John B. Kilroy
1977Kiaola
John B. Kilroy
1979Tenacious
R.E. (Ted) Turner
1983Condor
Robert Bell
1984Cachasa
Mike Gruener
1985Stormy Petrel
Blaine Nashold
1986Man O War
Sennett Duttenhofer
1987Scaramouche of Warwick
Arthur Bugs Baer
1988Saucy Sue
Lt. Cdr. Hardly Lewin, Jamacia Def. Force
1989Commodore Rucanor
Bruno Dubois
1990Saucy Sue
Lt. Cdr. Richard Russell, Jamacia Def. Force
1991Merry Thought
Jack King 
1992Challenge AmericaPatrick O'Callaghan
1993Pipe Dream
Dr. Scott Piper
1995Dear Friend
Bill Kardash
1997Dear Friend
Bill Kardash
1999Critical Path
William (Bill) R. Dooley
2001Bonkers
Bill Zartler
2003Zephyrus V
Robert McNeil
2005Thin Ice
Stuart Hebb
2007Carinthia
Frank Kern
2009Privateer
Ron O'Hanley
2011Genuine RiskHugo Stenbeck
2013ShockwaveGeorge Sakellaris
2015Shockwave 
George Sakellaris
2017


Elapsed Time Records

2017 WESTERN CARIBBEAN SERIES
PINEAPPLE CUP
CUBA CUP

Past Winners

Photos

History

2017 WESTERN CARIBBEAN SERIES


YearBoat NameSkipper NameTime
2005Titan 12Tom Hill2:10:24:42
2003
Zephyrus VRobert McNeil2:23:05:57
1971Windward PassageR. Mark Johnson3:03:40:07
1969Windward PassageRobert F. Johnson4:10:22:29
1963Bolero
Sally A. Langmuir
5:11:29:27
1961EscapadeBaldwin M. Baldwin
7:01:08:36


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.