May 13, 2021

Save the Date for the 35th Pineapple Cup Montego Bay Race!

The Montego Bay Yacht Club and Nigel Knowles, the Pineapple Cup Regatta Chairman are pleased to announce the 35th edition of the Pineapple Cup - Montego Bay Yacht Race will take place with two starts on January 22nd and 23rd, 2022.

We're excited to bring you information on the 35th edition of the Pineapple Cup - Montego Bay Race! If this race is not on your winter sailing calendar, what are you waiting for? This, as always, will be one of the most-fun and challenging races of the winter!

The Pineapple Cup is hosted by the Montego Bay Yacht Club with the support of the Storm Trysail Club and the Biscayne Bay Yacht Club and is organized by Manuka Sports Event Management. The event is once again open to multihulls and monohulls over 30 feet and will be scored under ORC and PHRF.

View the Notice of Race

What’s New in 2022?

The Pineapple Cup is once again open to multihulls and monohulls over 30 feet and will be scored under ORC and PHRF. In order to increase the overall enjoyment and reward of competing in this classic tropical ocean race, we have made one big enhancement for the 2022 edition.

We're adjusting how we award the most coveted trophy, the Silver Perpetual Pineapple Cup. NEW for 2022, 1st overall on corrected time will be awarded to the winner of the most competitive fleet. The most competitive fleet will be calculated by averaging the corrected time deltas of the first 80% of the fleet. The fleet with the lowest average deltas will be eligible to win the Pineapple Cup.

More Updates

A Word from MBYC Regatta Chair Nigel Knowles

It is now just under a year to go before the 35th running of our legendary Pineapple Cup race from Miami to Montego Bay, Jamaica. While we were disappointed to have to postpone the race this past January, we are looking forward to what we think of as one of the best ocean races around with not just fun and challenging conditions but great competition, and the warm water and sunshine in January that the Caribbean provides!

In 2019 we introduced a staggered start so as to ensure all boats finish much closer to one another. This allowed for bigger parties and more opportunities to enjoy the Montego Bay Yacht Club, famous for being one of the friendliest yacht clubs in the Caribbean and so we are looking forward to continuing that tradition in 2022.

New though for this year is the way in which we will award the coveted Pineapple Cup Trophy. We will be looking to the most competitive fleet as determined by finish delta. This will make the Pineapple Cup open to everyone who registers!

I invite you all to sign up early and help us bring in a large competitive fleet so we can get some great racing, exciting and fast sailing that all culminates in one of the most prestigious prizes and the best social on the sailing calendar.

I look forward to seeing you at the start of our 2022 Pineapple Cup race.


The Infamous Course!

It all started in 1961 and has continually run nearly every other year since...

One of the oldest offshore races on the calendar, The Pineapple Cup – Montego Bay Race started in 1961, making 2022 the 35th edition of the venerable 811 nautical mile race.

Immediately after the start, racers cross the Gulf Stream for the Northwest Providence Channel. The middle of the race offers a fetch down the eastern side of the Bahamas Island Chain toward the tip of Cuba. The final stretch is typically a sailor’s dream: a 240-mile downwind sleigh ride from Cuba’s eastern tip, known as the Windward Passage, to the finish at Montego Bay.

Registration is Open!