Please select your home edition
Edition
Maritimo S Series

35th Pineapple Cup Montego Bay Race set to start Saturday, January 21st

by Pineapple Cup 20 Jan 2023 16:25 UTC January 21-28, 2023
35th Pineapple Cup Montego Bay Race © Pineapple Cup

The Pineapple Cup-Montego Bay Race, an 811-nautical mile sailing race hosted biennially by the Montego Bay Yacht Club and Storm Trysail Club, with support from platinum partner Appleton Estate, is excited for the start of the 35th edition of the offshore classic.

The Pineapple Cup, first run in 1961, has seen a plethora of world class sailors competing on high performance racing sail boats since its inception. This year is no different as the modified Volvo70 owned by Roy Disney will be crewed by top sailors including 2-time America's Cup winner and Olympic sailor Peter Isler, 2-time Volvo Ocean Race winner Tony Mutter along with multiple Volvo Ocean Race competitors Daryl Wislang and Brad Jackson to name a few. Pyewacket has their sights set on the race record for monohulls last set in 2005 by Tom Hill's Titan 12 at 2 days, 10 hours, 24 minutes and 42 seconds.

The 2023 edition of the race has unfortunately suffered many late withdrawals due to a myriad of extenuating factors, leaving the race with three teams: Pyewacket 70, Callisto and Rikki. The three teams however boast exceptional sailing talent and it is anticipated to be hard fought event right down to the arrival in Montego Bay.

Jim and Kate Murray's Callisto, started as a small boat program on Lake Michigan and has evolved to Pac52 with a desire to compete in some of the top offshore races. Their crew is made up of past Volvo Ocean Race sailors including Justin Ferris, 52 Super Series sailors Jared Henderson and Ian Moore, Melges24 Champion Ansel Koehn and Sydney-Hobart competitors Ricky McGarvie and Mal Parker.

The third team is Rikki, a Reichel/Pugh 42 owned by Bruce Chafee. Rikki is made up of a largely amateur team from Boston is excited to be competing in their first Pineapple Cup. The team has competed in the Newport-Bermuda race and features a young crew with immense collegiate sailing experience.

Full crew lists for all teams can be found here

As part of the legendary welcome teams will be presented with Appleton Estate rum upon their arrival into Montego Bay. Following their arrival Appleton Estate will be the present Jamaica Night, a Jamaican themed party at the Montego Bay Yacht Club, and the Awards Ceremony.

"Although it's disappointing to have so many late withdrawals from this year's event, all of us at the Montego Bay Yacht Club are very much looking forward to greeting the teams upon their arrival in Jamaica with what we believe is the friendliest welcome around! This race has been sailed by some of the world's best and having such an outstanding group of sailors competing this year is an honor. The race is often referred to as an offshore sailor's dream of a beat, reach and run early indications show the forecast aligning with that for this year on what we hope is a competitive and fun event," said Nigel Knowles, Montego Bay Yacht Club Rear Commodore.

In an effort for all teams to arrive around the same time, there will be two starts. Callisto and Rikki will start on Saturday, January 21st while Pyewacket will start on January 22nd. Both starts will take place off South Beach, Miami with the warning signal at 11am.

The race will be available via YellowBrick tracking here, on the homepage of pineapplecup.com and via the YellowBrick app.

Related Articles

Boat Buying Basics
Melanie earned her US Coast Guard 100 Ton Master Captain's License before her car license Melanie Sunshine Neale earned her US Coast Guard 100 Ton Master Captain's License before she got her driver's license. She grew up living aboard her family's 47-foot GulfStar sailboat, cruising up and down the East Coast and the Bahamas for 20 years. Posted on 13 Sep
Racing & Events Manager role in Dubai
Dubai Offshore Sailing Club is looking for a Racing & Events Manager Dubai Offshore Sailing Club (DOSC), one of the Middle East's most established and internationally recognised Sailing Clubs, is inviting applications for the role of Racing & Events Manager. Posted on 13 Sep
Bulwarks and Bulldust – Show 7 Season 2
Episode Seven - XCAT World Champion, Tom Barry-Cotter from Five Blade Episode Seven - XCAT World Champion, Tom Barry-Cotter from FiveBlade talks boat shows, greenwashing. Lots to learn, so strap in for a great time. Posted on 13 Sep
Speak up for Striped Bass
Tell ASMFC to reject seasonal closures The Atlantic States Marine Fisheries Commission (ASMFC) is considering new restrictions on striped bass for 2026, proposing a 12% reduction for the recreational sector, which would require additional seasonal closures to achieve the reduction. Posted on 9 Sep
Marine Auctions: September Online Auctions
The bidding will open on Tuesday 23rd September The bidding for the September Online Auction will Open on Tuesday 23rd September and will close on Monday 29th September 2025. Entries are now being accepted for October's Online Auction. Posted on 9 Sep
Bulwarks and Bulldust – Show 6 Season 2
Episode Six - Marco Masia from MAN Distributor, Seapower Episode Six - Marco Masia from MAN Distributor, Seapower, about MAN Marine Diesels, their new MAN V12X, Solé Generators, carbon emissions, IMO Tier III and Euro V, greenwashing, and boat shows. Lots to learn, so strap in for a great time. Posted on 7 Sep
The Sportsman Insider, Episode 1
Unveiling the Open 402 Hull Welcome to the launch of The Sportsman Insider, a new series designed to showcase the progress of future models at Sportsman Boats. Posted on 6 Sep
Lowe Boats unveils all-new LF Pontoon Series
A versatile lineup of fishing-first pontoons Lowe Boats, a leading manufacturer of high-quality, full-featured aluminum boats, today announced the all-new LF Pontoon series, a versatile lineup of fishing-first pontoons designed for both passionate anglers and fun-seeking families. Posted on 31 Aug
Bulwarks and Bulldust – Show 5 Season 2
Greenwashing - Who is saying what, what can be believed, and what needs a load more inspection... Episode Five - ponders the topic of Greenwashing. We offer some thoughts on the matter and talk with Annika Thomson, Wes Moxey, and Greg Haines about their thoughts on this vast subject. The fifth episode of Series Two is now live Posted on 31 Aug
Marine Auctions: August Online Auctions Bids Open
To Finish Thursday 28th August 2025 at 2pm AEST The Bidding is open and will end Thursday 28 August at 2pm AEST. Posted on 27 Aug
Palm Beach Motor YachtsMaritimo S Series