Pineapple Cup Underway!

The 35th Pineapple Cup-Montego Bay Race is underway!

Rikki got off on a perfect start in a light, but building, southeasterly, the remaining teams will start tomorrow

Saturday, January 21, 2023 Miami, F.L. – Rikki, the young Rhode Island based crew, was the lone team to start today at 1105 ET, giving them a 27-hour head start on the remaining two teams Callisto and Pyewacket70. In an effort to ensure teams arrive into Jamaica around the same time, race organizers have implemented a staggered start. Sailors including Volvo Ocean Race and America’s Cup champions are taking part in this 35th edition of the 811-nautical mile race. Tracking will update every 30 minutes at:

Under sunny skies in a very light, but building southeasterly, Bruce Chafee’s Rikki crossed the Appleton Estate start line perfectly. The young team is made up of many recent collegiate grads who are getting the opportunity to step up into offshore racing from largely having only raced dinghies. For all of the crew, this will be their longest offshore race. 

Nigel Knowles, First Rear Commodore of the Montego Bay Yacht Club “With one boat involved, it was still very exciting, the conditions were near perfect, the breeze was picking up nicely and the seas were calm. As a spectacle it was a fantastic scene, Rikki set off toward the horizon on time and the crew are all very excited about their upcoming adventure to Montego Bay. Safe sailing to them.

Hugh Piggin, Race Director, “Rikki had a great start today. We have the two faster boats chasing them down tomorrow with a non-typical weather pattern for the course. If Rikki can keep moving, they have a shot at the line honors trophy. Looking ahead to tomorrow’s start, there’s a possibility for Pyewacket to break the monohull record, Callisto is no slouch and will be pushing hard for the Pineapple Cup. The tactical race will be between Miami and the windward passage and then it will be a physically demanding, constantly working, trade wind drag race to Montego Bay”

Pyewacket and Calisto will start tomorrow, Sunday, January 22nd at 1400 ET. 

Tracking is available on the homepage of and also via the YellowBrick tracking app and will update every 30 minutes. Further updates will be on both Facebook and Instagram.

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