top of page
Pineapple Cup Logo 2022.png


  • Facebook Social Icon

All the latest information on the Pineapple Cup can be found on the Pineapple Cup website

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.


Pineapple Cup Pic 1.jpg

On Friday, February 1st, after 811 nautical miles of ocean racing followed by packed out social events, the 2019 edition of the Pineapple Cup - Montego Bay Race reached its conclusion with the packed out Montego Bay Yacht Club playing host to the awards ceremony! Over 170 attendees including the Honorable Custos Rotolorum Bishop Conrad Pitkin, His Worship Mayor Homer Davis of Montego Bay, MBYC Commodore Nigel Knowles and Royal Jamaican Yacht Club Past Commodore Andrew Thwaites were on hand for the awarding of the Governor General's Trophy, also known as the Pineapple Cup.

Race Director Hugh Piggin said, “This has been an truly global Pineapple Cup - with some of the top offshore sailors in the world  representing 14 different countries to take on this historic race. 


From a heavy air start, a wind hole in the middle and a classic downwind finish, this edition provided exciting sailing for all of the teams. It was terrific to see Argo set a new course record, however with the modern sailing machines out there I think there is still opportunity to better both the monohull and multihull marks in future editions. Finally we made a few tweaks to the start times of the fleets which resulted in having all boats represented at the prize giving which made for an very exciting evening. Congratulations to Argo, Senara, Lady Mariposa - we hope to see you defend your titles in 2021."

Pineapple Cup Pic 2.jpg
Pineapple Cup Pic 3.jpg
Pineapple Cup Pic 4.jpg

Horst Baier, James Bill and Eamonn Delisser's Senara FARR 395 Racing had an exceptional race and their take of hardware at the Awards was impressive. The team was awarded the Silver Seahorse Trophy for their win in the PHRF division, the Seagull Trophy for being the smallest boat to finish and the and the newly created Felix Hunter Andre Trophy awarded to the winning boat with the most competitors. 

Eamonn said of the race, “This race started out rough. We lost our windex within the first 3-4 hours don’t know how, it just came off. We beat ourselves up to Eleuthera where we knew the cold front was coming in. We never expected 40 knots that was a surprise, but we knew the wind was going to change and we had to double reef and put up storm sails, but after that it was a pleasurable sail. 


This is my first win, in 8 this feels great. Jamaica is home [Eamonn was born in Jamaica, but resides in Miami], it is one of the greatest races out there, it has every condition you want to do and we started doing this because of my daughter (Arielle), it [the boat] was her graduation present. I just want to thank Jim Bill and Horst Baier because without them we couldn’t do this."

Pineapple Cup Pic 5.jpg

Skipper Nigel King, Lady Mariposa Racing said of the race, “It was a really enjoyable race - very different race. The conditions changed throughout the course. It was lumpy in the gulf stream from Miami and then you get through the Bahamas with quiet and flat seas and then obviously we had a good rip down towards Jamaica. I think everyone enjoyed it - it was nice and sunny. There were times it was colder than we thought it would be, but I think everyone really enjoyed it. It was a good length of race because you can really get into it - it was the longest race we’ve done for a while so it was good for us." 

Pineapple Cup Results 2019.png

Winner Of The Largest Fleet: 
First Monohull To Finish: 
The Silver Rose Bowl Perpetual Trophy – Wizard 
Smallest Boat To Finish: 
Seagull Trophy – Senara
Division PHRF: 
1st Silver Seahorse Perpetual Trophy – Senara
2nd – Renegade 
3rd – Sin Duda! 
Division Multihull 
Arawak Perpetual Trophy: Winner of Multihull Class - Argo 
(Multihull Record Breaking Winner) 
Division IRC: 
1st – Lady Mariposa 
2nd – Wizard
3rd – Conviction 
Navigators Trophy, First Overall Corrected Time IRC & PHRF (Shared)
IRC: Lady Mariposa – Audrey Yakunin 
PHRF: Senara – Joseph Goulet
OVERALL WINNER OF THE PINEAPPLE CUP – First Overall Corrected Time IRC Rated Boat 

Lady Mariposa

Pineapple Cup Pic 6.jpg
Pineapple Cup Pic 7.jpg
Pineapple Cup Pic 8.jpg
Pineapple Cup Pic 9.jpg
bottom of page