Third times a charm for Jamaica race

Published on January 19th, 2023

After health and travel restrictions cancelled the Pineapple Cup – Montego Bay Race in 2020 and 2021, the 35th edition is set to start in 2023 on January 21 and 22. Due to several late withdrawals, only three teams will take on the 811 nm course from Miami, FL to Montego Bay, Jamaica.

The Pineapple Cup trophy dates back to 1961 where it was handcrafted in London. Throughout the years, the trophy has been awarded to some of the most well-known names in yachting including: John Kilroy, Ted Turner, and Robert F Johnson.

Gearing up for the start are a mixture of teams, headlined by the modified Volvo 70 Pyewacket. Roy Disney and his team on Pyewacket which will be gunning for the monohull course record set in 2005 by the R/P 75 Titan 12 of 2 days, 10 hours, 24 minutes and 42 seconds.

Another strong contender will be the Pac52 Callisto. Jim and Kate Murray have been sailing on Lake Michigan for years, but recently they’ve ‘graduated’ from smaller boats to the 52-footer to take on many of the great offshore races. Their team, a pro-am mix, will be competing in the Pineapple Cup for the first time.

The third team is Rikki, a R/P 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 collegiate sailing experience. 

“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,” said Nigel Knowles, Montego Bay Yacht Club Rear Commodore. “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.”

In an effort for all teams to arrive around the same time, Callisto and Rikki start on January 21 while Pyewacket starts on January 22. Both starts take place off South Beach, Miami.

With no multihulls, the current course record should hold, set in 2019 at 2 days, 0 hours, 7 minutes and 44 seconds by the MOD70 Argo.


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