For the love of going to sea

Published on January 27th, 2023

Only three boats started the 2023 Pineapple Cup – Montego Bay Race, but their passion for offshore racing, and the 811 nm course from Miami, FL to Montego Bay, Jamaica, will be bringing them back.

Callisto Racing (Pac52), Pyewacket70 (modified VO70), and Rikki (R/P 42) competed in the 35th edition with Kate and Jim Murray’s Callisto Racing (above) claiming the Governor General’s Trophy for overall honors.

“There were a lot of questions about why you’d do a race with three boats and I’m going to answer that now,” said Murray. “You do it because it’s an epic race course and you do it because the people all share a common love of going to sea and laying it all on the line sailing with a great group of people. At the end of the day we do it because we love it.”

In addition to the Governor Generals trophy, the Silver Rose Bowl was presented to Pyewacket70 for fastest elapsed time for a monohull at 2 days 18 hours 22 minutes and 39 seconds.

“We have a lot of people to thank, first of all our owner Roy Disney couldn’t be with us this trip [due to injury], he was texting us every day, ten times a day, he was just so devastated he wasn’t here, so we’ll be back for sure,” said Gary Weisman, watch captain on Pyewacket70.

“Our boat gets around the course because we have a team of sailors that are just phenomenal, and it’s a pleasure from my perspective to go to sea with all of them. We will be cheerleaders, for the next Pineapple Cup, we’ve enjoyed it and we’d like to come back!”

Crew of Pyewacket70

The E.J. Garmhausen Perpetuaal trophy was presented to Ian Moore, the navigator on the Callisto for being the team to finish first overall on corrected time

Rikki received the Seagull Trophy for being the smallest boat to finish.

“As you can tell we were the youngest crew out here,” said Rikki owner Bruce Chafee. “For me, that’s the most exciting part because we have a group who’s energetic and learning and enthusiastic and a joy to be with. And then arriving here was really nice, the welcome on the dock, the welcome from the entire Montego Bay Yacht Club has been really wonderful thank you very much.”

Crew of Rikki


• Monohull course record set in 2005 by the R/P 75 Titan 12 of 2 days, 10 hours, 24 minutes and 42 seconds.
• Multihull/overall course record set in 2019 at 2 days, 0 hours, 7 minutes and 44 seconds by the MOD70 Argo.

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