Three Boat Crews Win Trips to Antigua and Barbuda Sail Week in Sag Harbor Regatta

There were plenty of prizes to go around following the Antigua & Barbuda Hamptons Challenge Regatta in Noyac Bay on Saturday.

Not only did top finisher John Pearson, skipper of Red Sky IV, and his crew win an all-expenses paid trip to the Caribbean island nation, but the Antigua and Barbuda Tourism Board extended similar offers to two other captains and crews in a surprise announcement at the post-race party at Bell and Anchor restaurant in Noyac.

Bill Coster and the crew of Silent Passage, who came in third place in Division 3, also won a trip to Antigua Sailing Week next year after they were honored with the Rob Roden Memorial Award, given annually to the boat whose crew seems to be having the most fun, and is given in memory of the founder of the challenge.

In a repeat of last year, when an extra grand prize was handed out to a boat with an all-female crew, Caitlin Cummings and the crew of Cat Boat, who took second place in Division 2, were shocked to learn that they, too, would be given air fare, lodgings, and use of a boat at next year’s race week.

On top of that, the Antigua and Barbuda Ministry of Tourism made a $6,000 donation to i-tri, the empowerment program for adolescent girls founded by Theresa Roden, which is the beneficiary of the regatta.

Antigua and Barbuda take the event seriously. The country’s minister of tourism, investment, aviation and transportation, Charles “Max” Fernandez, attended the event, along with several other officials, as he has done several other years.

“It was a night full of surprises,” Roden said. The ministry’s donation, which will be augmented by proceeds from the regatta and raffles, “is coming at a really great time as we expand our program, ensuring that we can be there for the next group of girls.”

In the days leading up to Saturday’s race, organizers were worried that the remnants of Hurricane Debby would result in dangerous wind gusts and drenching rain. Instead, when the storm passed farther inland than originally expected, the concern shifted to whether there would be enough wind.

“On Friday, the wind gusts were up in the mid-30s,” said race director Greg Cukor, “but it changed to lighter winds,” forcing him to shorten the course to ensure that slower boats would be able to finish in the three-hour allotted time.

A total of 23 boats in three different divisions competed. “Red Sky was a well-sailed boat,” Cukor said, of Pearson’s boat, which finished first over all. “They did everything right.”

Pearson, of New Hampshire, is a Long Island native who sailed on the East End as a child.

“It’s a great prize to win,” he said. “Normally, when we win, we just get a pickle dish. To get something of that value is great for the crew. We’re ecstatic.”

Pearson, who sailed on America’s Cup boats at the New York Maritime College in the early 1980s, said Red Sky IV, a J-111, “is an amazing boat. It’s fast, and it’s very sensitive. Once you figure out its sensitivities, it can be really good.”

The winning captain said he would be turning 65 in the coming days. “Here I am doing what I was doing at 9,” he said. “I loved it then, and I still do.”

Typically, the winner of the Bob Roden Memorial award gets a glass plaque, so Coster, who lives in Laurel, was stunned to learn that he and his crew would be flown down to Antigua and Barbuda next spring for the event.

“We can’t wait,” he said. “This is a big deal to be able to take five people. We didn’t expect that.”

It won’t be Coster’s first visit to the islands. He said he won a raffle prize at an earlier Challenge. “It’s a wonderful place,” he said. “The people are charming.”

Coster said he was fortunate to sail with a good crew. “It was light, variable winds for most of the race until close to the end, the wind came up, which is pretty common,” he said. “It was challenging, but all credit goes to my crew.”

His boat, Silent Passage, finished third in Division 3 and eighth overall.

Cummings and the crew of a boat borrowed from Breakwater Yacht Club that was christened for Saturday’s race “The Cat Boat,” with a swipe of the claw at Republican Vice Presidential candidate J.D. Vance, were perhaps the most surprised to win a trip to Sailing Week.

“We had no inkling at all,” said Cummings, a graduate of SUNY Maritime, who is a marine engineer working in the engine rooms of container ships and tankers in her work life. “We are super excited.”

Like the other captains, she said her crew performed well, given the spotty wind.

Cummings and her crew were also honored with a new award given in memory of Bruce Tait, a yacht broker, founder of the Breakwater Yacht Club and a well-known figure in the local sailing scene, who died recently.

The top two boats across the line besides Red Sky IV were Glory Days skippered by Peter Beardsley, which came in second, and Gypsy Moon, captained by Doug Davies.

Additional information about the regatta can be found at the Peconic Bay Sailing Association’s website, pbsa.us.