Passing the Passion: Desmond Family Carry On Tradition of Caribbean Sailing

Posted in ,

After college Jon Desmond spent four years in his early 20s sailing the Caribbean on his dad Jack’s Swan 48 Affinity and that’s how he got to know all the islands around the BVI.

“We raced Affinity around the Caribbean on the circuit – St Maarten, Antigua, St Thomas, BVI, and the boat went back and forth between home in Marion and here, a lot of deliveries,” Desmond noted.

The impact of that experience?

“It makes you fall in love with the islands down here, right?! It’s awesome sailing down here so that’s the impact,” he smiled.

Carrying on the family tradition of racing and cruising in the Caribbean, Desmond, who grew up sailing around Marion, MA, and Buzzards Bay is keen to do the same with his kids – Jackson (7) is already taking sailing classes back home in Marian MA, while the younger two, Hunter (5), and Teddy (3) were happy to be cruising this past week in the BVI.

“We chartered a Lagoon 50 prior to BVI Spring Regatta and cruised with the kids to give them a taste of pretty islands and beaches,” Desmond said. “The five-year-old said after day three, “Can we just live here all the time?” I liked that! My dad was down here also on a catamaran he chartered so we had three generations out cruising, it was good.”

This week, Desmond is racing Final Final, his Mills 41 built in Hong Kong which he bought it in 2022. He was doing a lot of boat shopping at the time and the previous owner had been very successful with her. She’s a very sporty boat for only 41’, he noted, and a good step into the sport boat world.

He bought the boat and shipped her from Hong Kong back to Newport, RI, with the intent to mostly do offshore racing and check a few boxes; he successfully completed the Chicago Mackinac race last year placing first in class. He also raced four Caribbean events last year which was awesome but hard with a young family.

“I went back and forth four times which created a little stress on the home front (!) which is why we did the two events this year and made them bigger and longer. I was in Antigua for two weeks with just my crew and now I’m in the BVI with my family.”

This year, prior to BVI Spring Regatta, Final Final competed in the Nelson’s Cup Series in Antigua and the RORC Caribbean 600.

“For Nelson’s we got put in a class with the big 50-footers, the TP52, and RAN another 52’er, so that was a little challenging racing against them as a smaller boat but the 600 went great, we finished 7th overall in IRC with about 60 boats. We were very pleased with that.”

Serious competition is important to Desmond, so he does his best to optimize his boat for racing in the Caribbean. He spent a lot of time in the Caribbean 600 doing trial certifications under IRC and just trying to see how different sails impacted the rating, and has been studying CSA for the same reasons, not wanting to race at a disadvantage. Either way, he’s finding that the boat’s sweet spot is in lighter air.

“We’ve now raced a lot against the RP42 Rikki, they also did all the Antigua races this year. In the lighter breeze we can be pretty competitive with them. Earlier this week when it was pretty windy, they sailed away from us pretty good. It’s always fun sailing  in the big breeze but for results, we do better when its lighter.”

Looking forward, Desmond is keen to continue checking off the bigger offshore races, like Fastnet and the Middle Sea race. He’s already thinking about a bigger boat for that purpose.

“I do love Final Final but I also love looking at other boats! The team (note he has Kiwi pro Cameron Appleton on board this week) is already looking at something bigger as my focus right now is doing offshore stuff,” he said, adding, “I do some of the IC37 racing so I do get my one design fix in during summer in Newport.”

BVI Spring Regatta 2024,