Johnny May has seen it all!

What’s it like to finish every boat in the Pineapple Cup since 2007?

Johnny, how did you get involved with the Pineapple Cup?
I serve on the race committee at Larchmont YC in New York and served as its chairman for eight years, so it was a natural fit when my brother Frank May, who was a former chair of the Race and flag officer at the Montego Bay Yacht Club, asked me to come down to serve on the race committee at the finish. The rest you could say is history.

What is your role with the race?
I guess I’m called the Finish PRO. My responsibility is to be on station and finish all competitors correctly and safely.  Since 2007 I’ve finished every single boat from the first to finish until the last boat crosses, I’m on call 24/7.

What keeps you coming back year after year? 
Everything. The camaraderie of all the competitors coming together at the post race activities.The overall welcoming spirit when your boat is finally tied off at the dock. The overwhelming generosity from the members and staff of the Montego Bay YC make it so easy to enjoy.

What advice would you give to new competitors?  
You’ll find it’s the most beautiful ocean race in the world. It’s the definition of the perfect beat, reach and run. Please prepare to sail fast and sail safe.

You’ve seen a lot of finishes over the years, any one in particular that stands out to you?
The 2019 Overall Winner “Argo”, a Mod 70. Watching her catch up and leap-frog the fleet after her start a day later was impressive. 

Why should a team put the Pineapple Cup on their list of races to do?
Whether your boat is crewed by Professionals or Corinthians, families or friends, you’ll find this race to be challenging and rewarding at every level! And, for the price of an entry fee, you can and will be racing against some of the best ocean racers in the world!

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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