World’s longest Sunfish race set to circle Shelter Island this weekend

The longest Sunfish race in the world kicks off this weekend at the Southold Yacht Club.

Seventy-four Sunfish boats are registered to set sail at 11:30 a.m. Saturday in a race that dates back more than half a century and includes sailors who traveled here from up and down the eastern seaboard, including Florida, Virginia and New England.

“This race is absolutely unique,” said Beth Fleisher, the club’s race committee chair. “Sunfishes are small, 14-foot boats. We normally sail a race that takes maybe 15 minutes, half an hour, maybe 45 minutes. That’s how you race small boats — in many races over the course of a day.

“But this race circumnavigates Shelter Island,” she said, which is roughly 26 miles, the length of a marathon.

“It’s uniquely challenging because Sunfish sailors are using skills that they don’t normally use. You have to sail continuously in these very physically active boats for, oh, the top boats come in around four hours, depending on wind.”

The sailors set out in nearly any weather except electrical storms, Ms. Fleisher told Suffolk Times.

“We’ve had lots of wind. We’ve had no wind — when we had to make the race shorter because the boats just didn’t have enough wind to get around. We’ve had races where it’s been just been blowing stinking raining. It’s the whole nine yards. Whatever the weather gods can throw at you, that’s what we get.”

In many ways, the race is a nautical marathon.

“Just to complete this race — about 26 miles, which is a heck of a lot in this little tiny boat, for a minimum of four or five hours out there — so to complete in this is a really big deal,” Ms. Fleisher said. “We make sure unlike in any other races, that not only do we give out the standard trophies and whatnot, but we give out nice looking certificates of completion.

“Not everyone that starts, finishes,” Ms. Fleisher cautioned. “Every year we have people who think that this is something that they can do, and they want to do, and they decide part way around [that] they’re done.”

Asked how sailors should best prepare for such a long race, Ms. Fleisher demurred.

“Let’s put it this way,” she said. “I don’t tell anyone what to do but you’re certainly going to want to be in good physical shape and in good shape. You want your boat to be in good shape so your boat doesn’t break. You want your body to be in good shape so your body doesn’t break.”

She said the first 10 boats receive awards, but there are also trophies awarded to the oldest person to complete the course, the first person over 50 to complete the course, and several other categories.

She said hot doggers should think twice.

“It’s not like, ‘oh, I’m a young, fit, 24-year-old so I have the advantage’ – that’s not true.”

And then there are the currents.

“Whether you’re in a big boat, a keel boat, a 40-footer or this 14-foot boat, there are wicked, wicked, wicked currents and tides around Shelter Island. There’s back eddies,” she warned. “If you look at a chart of the waters surrounding Shelter Island … the water at times is nine feet deep and the water at times is six inches deep.

“All those variations in depth, and the currents and the tides flowing around Shelter Island and the other shores create wicked whirlpools and back eddies and fast running currents. So if you’re in a boat that goes maybe four or five knots and the current’s against you at like two knots or more — which can happen around South Ferry — and you’re not sailing correctly, in relation to that current, you’re doomed. It’s really fun,” she concluded, “but it’s not casual.”

She called the race “a real test of all sorts of aspects of sailing.

“Of athleticism smarts can you figure out what current is best and most advantageous? Can you figure out where to put your boat so either you’re getting into the current when the current’s running with you, or getting out of the current when its running against you? Can you sail where the wind is going to be strongest?

“Most races you’re sailing around buoys. This race, there are no buoys. You just have to sail around the island, and you can sail as close to the shore as you want, but if you run aground and you hit what you have to do is walk your boat backwards, because you can’t advance the boat over land. And if you hit a rock, you should have known it was there. So it’s really wildly fun and interesting.”   

A small army of volunteers is expected, not just from Southold Yacht Club but nearby clubs including Menantic Yacht Club on Shelter Island and New Suffolk’s Old Cove Yacht Club.

“We have motor boats that stay with the fleet so that if anything happens to anybody they can safely get back to the yacht club,” Ms. Fleisher said.

While nearly every boat is sailed by a single competitor, there are a few two person teams competing, including two “older, adult sisters” and a pair of father-daughter teams.

“This is an annual traditional for them, even though it’s not that comfortable to have two adult human beings in one of these little boats. We give a separate trophy for the first boat with two people in it to come in.” 

While a teenager must be at least 15, with parental permission, to compete, there are also racers who are in their 60s, 70s and even 80s, Ms. Fleisher said.

Once again this year, the race will include Joe Sullivan, 86, who dreamed up the race in the first place.

In the summer of 1970, as a fairly new member of the Southold Yacht Club, he was sitting on the shore, gazing across the bay to Shelter Island. He turned to one of the club’s officers and asked what he thought at the time might sound a silly question.

“Has anybody ever sailed a Sunfish around Shelter Island?” The officer didn’t know. So he checked with the club’s race committee chairman, who didn’t think so. So in the summer of 1971 he and a group of members launched a tradition that continues today.   

“I was aware that there was a long-distance Sunfish race in Connecticut, so I looked at a map and plotted it out and I said, ‘I think ours is longer.’

“So we called it the ‘World’s Largest Sunfish Race Around Shelter Island, N.Y.’”

The young sailor set about plotting what time of day would be best to start the race. He studied the tide charts and made a determination.

“I wanted to make sure we would start with the current going out, so that by the time we got to Gardiner’s Bay, for example, the tide would be changing and the current would start coming back with us. That would be the ideal.”

“But of course, not being familiar with the tide charts I read them incorrectly and the very first race in 1971 at the start the tide was coming in, and that proved to be quite a problem.”

“It was a miserable experience.”

Mr. Sullivan was mortified, he said.

At the awards ceremony following the inaugural race, “I got up and I apologized to the group.

“I said, ‘look, everybody, we never did this before. It was a first time experience. I know it was pretty rough,” he continued, feeling awful, “and it didn’t make a lot of sense.”

When he promised that it would be the first and last such race, he said, he was bombarded with booing.

“No, no! We loved it! It was great!,” he said, laughing as he recalled the crowd’s enthusiasm.

“They were very, very psyched!”

Mr. Sullivan said this year will be his 50th and final race.

Having finished fourth last year, and tenth the year before, he’s gunning for the top spot again this year.

“I’m not throwing in the towel,” he said with a laugh. “There are guys older than I that have won this race.”

Southold Yacht Club is located at 165 North Parish Drive in Southold. Registration and breakfast begin at 8:30 a.m. and after the race there will be an awards ceremony with beer and a buffet.