News

While it was devastating to announce the unavoidable postponement of the 2025 Pineapple Cup-Montego Bay Race., we are really excited to announce the next edition of

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

At 08:00:51 on Thursday, January 26, the Rhode Island based team Rikki crossed the Appleton Estate finish line. The team’s elapsed time was 4 hours

At 21:21:07 on Wednesday, January 25th, Callisto Racing was second across the Appleton Estate Finish Line giving them an overall elapsed time of 3 days

Pyewacket70 captures line honors in the 35th Pineapple Cup – Montego Bay Race Pyewacket70 finishes with an elapsed time of 2 days 18 hours 15

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

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

1st Race Start Tomorrow at 11a ET We’re just under a day away from the first start in the 35th edition of the Pineapple Cup-Montego

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