JM | Jan 28, 2023

Callisto wins the 35th Pineapple Cup – Montego Bay Race

/ Our Today

Reading Time: 3 minutes

Silver perpetual trophy presented to Callisto at Pineapple Cup Awards Evening presented by Appleton Estate celebrating 2023 race

The winning Callisto team receive their Governor General’s Trophy.

On January 25, the Montego Bay Yacht Club celebrated Callisto Racing, Pyewacket70 and Rikki in the 35th edition of the Appleton Estate Pineapple Cup – Montego Bay Race.

Callisto Racing, owned by Kate and Jim Murray, is the overall winner of this edition of the Pineapple Cup. 

The  Governor General’s Trophy, also known as the Pineapple Cup, is one of the oldest yachting trophies dating back to 1961 where it was handcrafted in London. 

Throughout the years, the trophy has been awarded to some of the most well known names in yachting, including John Kilroy, Ted Turner and Robert F Johnson.

The Silver Rose Bowl winning team from the Pyewacket70.

The winner of the 2023 Governor General’s Trophy was awarded to the first-place team on corrected time in ORC, which was Callisto.

“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 Jim Murray, owner of Callisto.

“You do it because it’s an epic race course and you do it because the people here tonight 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 and we get to spend time with people like you, so thank you for putting on this race and thank you for having us and thank you all for what has been a terrific time.”

“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.”

Gary Weisman from Pyewacket

In addition to the Governor General’s Trophy, the Silver Rose Bowl was presented to Pyewacket70 for fastest elapsed time for a monohull at two days 18 hours 22 minutes and 39 seconds. 

Gary Weisman from Pyewacket, said: “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. 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!”

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

The Seagull Trophy winning team from the Rikki.

Rikki received the Seagull Trophy for being the smallest boat to finish and the Felix Hunter Andre Trophy awarded to the first boat to finish on a Saturday start.

Felix was a long time member of the Montego Bay Yacht Club, and was an integral part of the Pineapple Cup organisation for decades. Anyone who ever raced the Pineapple Cup or sailed into the Montego Bay Yacht Club knew her. The trophy was presented by her husband, Etienne.  

Bruce Chafee, owner of Rikki, said: “This is a great fun event for Rikki. As you can tell, we were the youngest crew out here and for me, that’s the most exciting part because we have a group whose 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 Spencer and the entire Montego Bay Yacht Club has been really wonderful. Thank you very much.”


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