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

January 19, 2022, MIAMI, FL, USA – 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. The full crew list can be found here. 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 at this LINK, on the homepage of  https://pineapplecup.com and via the YellowBrick app.

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 21st – 1100 – First Signal for Main Fleet
  • January 22nd – 1100 – First Signal for Fast Fleet
  • January 25th – Appleton Estate Jamaica Night at the Montego Bay Yacht Club
  • January 26th – Appleton Estate Awards Ceremony at the Montego Bay Yacht Club

While the silver Pineapple Cup is the most coveted trophy, the Montego Bay Yacht Club presents a number of awards to the teams and this year will be no different. Trophies to be presented include: 

SILVER PINEAPPLE CUP PERPETUAL TROPHY – For 1st overall corrected time monohull.

ROBERT McNEIL MOBAY COURSE CHALLENGE TROPHY – For the 1st monohull boat to break the Montego Bay Race 811 nm course record of 2 days, 10hrs, 24min, and 42sec set in 2005 by “Titan 12”.

FELIX HUNTER-ANDRE CUP – For the 1st place boat in the class that has the greatest number of entries that start the race.

SILVER ROSE BOWL PERPETUAL TROPHY – For 1st monohull boat to finish.

SILVER SEAHORSE PERPETUAL – For 1st overall corrected time PHRF rated boat.

E.J. GARMHAUSEN PERPETUAL TROPHY – To the navigator for the team that finishes 1st overall on corrected time. 

THE JAMAICA TOURIST BOARD LOG AWARD To be awarded to the most interesting boat log, to be determined at the discretion of the Montego Bay Yacht Club Race Committee. Creativity is encouraged!

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