Official page for the Pineapple Cup - Montego Bay Race, the biennial race from Florida to Jamaica.
The Pineapple Cup is an 811-nautical mile race that starts in Miami on January 21/22, 2023 & finishes in beautiful Montego Bay Jamaica. It is one of the oldest races on the sailing calendar.
21/01/2025
The Pineapple Cup is going virtual! Virtual Regatta is hosting this year's Pineapple Cup. Starting January 25th you can race from Miami to Montego Bay while in the comfort of your chair. To register and learn more --> https://www.virtualregatta.com/offshore-game/
12/08/2024
Being on the water lends itself to great times with great people. What are some of your favorite Pineapple Cup memories?
Registration is OPEN ---> https://pineapplecup.com
Ready. Set. Go! 🏁
The Pineapple Cup - Montego Bay Race returns on January 25th, 2025 👏🌴🎉
Registration is open --> https://pineapplecup.com/
07/12/2023
We are saddened to report the passing of Caroline Salisbury. Anyone who has participated in the Pineapple Cup will surely remember Caroline who spearheaded the many different awards presented to teams with the best boat logs.
Caroline LOVED a good story and would be sure to let you and your team know if your stories passed muster for her awards. She delighted in reading about all of the adventures, camaraderie and funny moments. From awarding the cook on the last place boat to finish, to crayons for the team with the best illustrations, a Murphy's Law Award, and of course the coveted Best Overall Log Book. Caroline took great pride in making sure the lesser known stories of the race were told.
She will be dearly missed by both the race and the Montego Bay Yacht Club. A memorial will be held at the Club on Friday, December 8th at 5:45pm.
Congratulations Pyewacket on capturing another line honors in this year's Caribbean 600! 👏💥💪
30/01/2023
Sailing into Monday with some fantastic drone shots from 's run into Montego Bay last week 👏👏
27/01/2023
"There were a lot of questions about why you'd do a race with three boats and I'm going to answer that now. 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." - Jim Murray Callisto Racing Read More --> https://www.pineapplecup.com/post/callisto-wins-pineapple-cup
27/01/2023
What a night at the Appleton Estate Pineapple Cup Awards Ceremony!
Congratulations to Callisto Racing 2023 Pineapple Cup Champions!
A big shout out to Pyewacket70 and Rikki! Thanks to the teams and all of the volunteers who helped make this 35th Pineapple Cup a success!
26/01/2023
Rikki crossed the finish line this morning at 08:00:51. This team made up of mostly young dinghy sailors had a great run into Jamaica in their longest offshore race yet!
Well done guys and girls! 👏👏👏
Rikki Finishes Pineapple Cup 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 20 minutes 55 seconds and 51 seconds. Rikki, owned by Bruce Chafee, is a crew predominantly made up of young recent collegiate dinghy sailors, all of wh...
26/01/2023
Congratulations Rikki and welcome to Jamaica! They crossed the Appleton Estate Finish Line at 08:00:51 👏👏
Last night after arriving Callisto Racing’s Jim Murray shared his thoughts on a solid race that felt like three races for the team.