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Callisto wins the 35th Pineapple Cup – Montego Bay Race! The Silver perpetual trophy was presented to Callisto at the […]

At 08:00:51 on Thursday, January 26, the Rhode Island based team Rikki crossed the Appleton Estate finish line. The team’s

At 21:21:07 on Wednesday, January 25th, Callisto Racing was second across the Appleton Estate Finish Line giving them an overall

Pyewacket70 captures line honors in the 35th Pineapple Cup – Montego Bay Race Pyewacket70 finishes with an elapsed time of

Pyewacket70 and Callisto set off in the 2nd race start of the 35th Pineapple Cup Both teams got off to

The 35th Pineapple Cup-Montego Bay Race is underway! Rikki got off on a perfect start in a light, but building,

1st Race Start Tomorrow at 11a ET We’re just under a day away from the first start in the 35th

January 19, 2022, MIAMI, FL, USA – The Pineapple Cup-Montego Bay Race, an 811-nautical mile sailing race hosted biennially by the Montego

2-Week Countdown to the 35th Pineapple Cup! With two weeks to go until the start of the 35th Pineapple Cup-Montego

What’s it like to finish every boat in the Pineapple Cup since 2007? Johnny, how did you get involved with