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The time is now to register for the 35th Pineapple Cup - Montego Bay Race!


The seasons are starting to change in much of the northern hemisphere signaling the time is now to plan your winter sailing races. And there's no better race to put on the calendar than the Pineapple Cup-Montego Bay Race! First raced in 1961, this winter classic is back for the first time since the pandemic and all of us couldn't be more excited to welcome sailors and their families back to the friendliest yacht club around! The race is 811-nautical miles of tropical water sailing starting in Miami and weaving its way through the Bahamas, around the eastern end of Cuba to the famous Montego Bay. After the sleigh ride into Montego Bay, the welcome the teams receive at the Montego Bay Yacht Club like none other and the yacht club members relish in welcoming all of you back to the island. The storied history of this ocean racing classic has a list of past winners any team would be envious of joining. Some of the biggest names in ocean racing including Ticonderoga, Kialoa, Tenacious, R.E. and more recently Shockwave, Prospector and Lady Mariposa have all raised the iconic Pineapple Cup. Being a tropical race from America's east coast and the longest running race from the US to the Caribbean, it is a must add on the bucket list of ocean races. The Pineapple Cup offers ORC, PHRF, Multihull and double-handed classes, so no matter what you sail or how you sail it, there is challenge and adventure to be had. And new for this year, the Pineapple Cup will be awarded to 1st overall on corrected of the most competitive fleet.

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Schedule of Events

In addition to being a fantastic on water race, the social functions are a highlight of the race. In addition to the presentation of one of yachting's oldest trophies in the Pineapple Cup, the Montego Bay Yacht Club social events will gain the support of Appleton Estate who will no doubt make these must attend events upon arrival into Jamaica!

• January 20th - Skippers Meeting and Send Off Drinks

• January 21st - 1100 - First Signal for Main Fleet

• January 22nd - 1400 - First Signal for Fast Fleet

• January 25th - Appleton Estate Welcome Drinks

• January 26th - Jamaica Night

• January 27th - Awards Dinner

What's new for the 35th edition of the classic ocean race?

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 2023 edition.


We're adjusting how we award the most coveted trophy, the Silver Perpetual Pineapple Cup. NEW for 2023, 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.

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