Meet the Teams

1st Race Start Tomorrow at 11a ET

We’re just under a day away from the first start in the 35th edition of the Pineapple Cup-Montego Bay Race. The first start will be tomorrow (Saturday) at 11am ET, just off South Beach in Miami. The second start will be Sunday, January 22nd at 2pm ET. 

While the race will be smaller in terms of competitors, the entry list features some of the top sailors and teams around AND the celebration in Montego Bay thanks to Appleton Estate will be bigger than ever! 

Tracking will be available on the homepage of and also via the YellowBrick tracking app. PLUS, don’t forget to follow us on social for further updates on both Facebook and Instagram.

Gearing up for the start are a mixture of teams, headlined by the modified Volvo 70 Pyewacket. The team includes 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.

“Pyewacket, the name of the boat, has a fairly long history with the Pineapple Cup. There’s about four or 5 of us that did a number of Jamaica races with Roy’s father, Roy E. Disney and we always had a fun time on the race, it’s one of our favorite races. 

Of course we would like to beat the record…this boat is very capable of beating the record and not in the same kind of conditions it was beat in 2011, if we had those conditions we’d easily beat it easily as long as we didn’t break the boat. Yeah, we’d like the record, right now our models are showing we have a shot, but it’s totally up to the weather. ”  
-Captain, Gary Weisman

Jim and Kate Murray’s Callisto, started as a small boat program on Lake Michigan and has evolved to a 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.

“We bought this boat at the end of 2019 and a goal has always been to do offshore distance racing competitively and in particular focusing on the big legendary ocean races. We’ve done the TransPac, California Race Week, Caribbean 600 and the Bermuda Race. 

We’re a ProAm program, we have a group of six really world class pros not just with experience ocean racing, but ocean racing 52s. I don’t think anyone on the team has done the Pineapple Cup, it’s been on our bucket list, it’s kind of what we call our Pirate Series as racing the Caribbean has always been a dream. 

The thing about our team is that we have a group of amateurs, that are really supported by the Pros, so we look at this race as a 4-day offshore sailing academy. We’re a group of friends who all just love being offshore and it’s rare to find a group of professionals who are patient, good teachers and good coaches.”
-Owner, Jim Murray

Bruce Chafee’s Rikki is Rhode Island’s team, with most everyone except two hailing from the tiniest state in the U.S. In addition, the crew features a mix of many young up and coming sailors who have all competed collegiately and are taking their sailing to the next level in what will be their longest offshore race to date.

“Most of us are from Rhode Island, but a couple from Maine and Florida. A lot of us are recent college grads from the spring of ’22. We’re all avid dinghy sailors and love college sailing. 

This boat did the Bermuda Race this summer and that was our first 600 mile race on the boat but this will be the longest Rikki has done. The boat was built in New Zealand in 2011 and shipped over to the US in 2018 when Bruce (the owner) bought it and she is the only boat of her kind. 

We’re looking for hopefully a downwind sleigh ride at some point in big breeze, that’s what Rikki does best in.

We’re all avid music fans, the boat is named after the Steely Dan song Rikki Don’t Lose that Number, we all love 70s music which makes for good bonding offshore. “
-Trimmer, Adrian van der Wal

Schedule of Events

  • January 21st – 1100 – First Signal for Main Fleet
  • January 22nd – 1400 – First Signal for Fast Fleet
  • January 25th – Appleton Estate Jamaica Night at the Montego Bay Yacht Club
  • January 26th – Appleton Estate Awards Dinner at the Montego Bay Yacht Club

Special thanks go to the Warrior Sailing Program and the Miami Yacht Club who have both been instrumental in providing race support for the start in Miami. 

Warrior Sailing provides maritime education and outreach for wounded, ill and injured service members and veterans. We do so by facilitating opportunities for skill development and building partnerships between the military and marine communities. Using sailing as a platform, Warrior Sailing positively impacts the participant’s physical and mental health while reconnecting them with the camaraderie and teamwork previously found in military service.

For over 80 years the Miami Yacht Club has been actively working with the community to foster an appreciation in the beautiful waters of Miami. They teach children, teenagers and adults to sail through the Miami Yacht Club Youth Sailing Foundation. They also host the City of Miami Marine Patrol and Underwater Recovery Unit. Their sailors have represented Miami Yacht Club all over the world: from youth events to the Olympics.

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