Sailing: Southold Yacht Club’s Croasdale wins Sunfish race around Shelter Island

A Sunfish sailing race can boil down to a series of decisions/gambles for competitors: when to tack, how to react to the currents and wind conditions, whether to steer close to shore or head to deeper waters, etc. Any one of the choices can spell the difference between first place and finishing at the back of the pack.

Joe Croasdale made enough of the right decisions Saturday to take top honors in the 51st annual World’s Longest Sunfish Race, Around Shelter Island, NY. Croasdale, 59, representing the host Southold Yacht Club, prevailed in an interesting fight to the finish, the second time he has won this race.

“I made one great choice and two bad choices,” said Croasdale, who also won this event 39 years ago. “It easily could have been flipped the other way around, and you’re in 25th place.”

As it was, Croasdale had the winning moves on a day of light wind. A nautical marathon, the race around Shelter Island typically covers about 25-26 miles, but a makeshift finish line was established just before the South Ferry to shorten the slow-moving, clockwise race around the island.

With about two miles left, Croasdale was among the leading foursome when he “jumped ahead just a little bit. Then they advised us they were going to shorten the finish line and I could see it up ahead and I had what I thought was a comfortable lead, but I could also see the wind die out before the finish line, and I saw [Jennifer Truscott of Westhampton Yacht Squadron] behind me catching up a bit, so it was tough. I didn’t feel a hundred percent confident until the last 30 seconds. It was just, a lot can go wrong.”

For him, though, it ended right. He said he finished in 4 hours, 51 minutes, about a minute ahead of the runner-up, Truscott. Robert Finora of Old Cove Yacht Club was third and Joe Sullivan of Southold Yacht Club fourth.

“I screamed,” said Croasdale, who was 20th in last year’s 50th race. “I was so ecstatic.”

Croasdale said Sullivan was the only one who got off to a better start than he did, with a decent breeze pushing them early on. A tactical mistake in Greenport waters cost Croasdale, though.

“I went to the Greenport side instead of the Shelter Island side and I pretty much let about 10 boats get in front of me and they all went close to shore and I went out in Gardiners [Bay]. I went out toward Bug Lighthouse and picked up a little current, and it paid off.”

It was while he was in Gardiners Bay with a big lead that Croasdale said he thought to himself, 

“I got it.” He said: “But then I’m like, ‘No, no, no. There’s way too much time left. Stop thinking that.’ ”

Croasdale has been sailing long enough to know one of the sport’s cardinal rules: Take nothing for granted.

He lost that lead with another “bad tactical decision.”

By the time all was said and done, Croasdale had been in his Sunfish for seven hours. “My quads are shot today, and that’s two days later,” the Oyster Bay Cove resident said in an interview.

“I really enjoyed this one more,” he said, comparing it to his first victory. He continued: “It was more enjoyable just because of the many years of experience. Being 59, I don’t have many of these left.”