Pyewacket 70 set to compete in 2023 Pineapple Cup-Montego Bay Race

Roy Disney’s Pyewacket 70 set to compete in the 35th Pineapple Cup

As preparations heat up for the 35th Pineapple Cup-Montego Bay race, we’re excited to announce that Roy Disney’s turbo charged Volvo70 Pyewacket has entered the race!

This team and boat are ready for the 811-nm race and they have their eyes on not only the coveted Pineapple Cup, but also the monohull course record. The current monohull record was set in 2005 by Titan 12 with an elapsed time of 2 days 10 hours 24 minutes and 42 seconds. 

Thinking about racing? There’s still time to register! This year 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.

Schedule of Events

In addition to being a fantastic on water race, the social functions are a highlight of the race. This year 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 at the Montego Bay Yacht Club
  • January 27th – Awards Dinner at the Montego Bay Yacht Club


Wondering where to stay, where to dock and what to expect upon arrival into Montego Bay? The logistics page has all of the info you’ll need for the race (and if you need more, feel free to email us at any time).

PLUS, the Secrets St. James, a luxury all-inclusive adults only resort, is offering Pineapple Cup competitors a discounted rate. Please visit their website and follow the instructions below to book. 

  • Select the date of travel
  • Select the “Enter discount code” option under the “change search”
  • Add group code PINECUP all caps
  • Select your room category

The Pineapple Cup will be awarded to the winner of the most competitive fleet in 2023

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.

This year we are adjusting how we award the most coveted trophy, the Silver Perpetual Pineapple Cup. 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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