Around Long Island Regatta: What it's like to compete in LI's premier sailing race

Against a backdrop of the usual bustling ferries and commercial traffic on New York Harbor, 71 sailboats circled near the Statue of Liberty, awaiting the start of Long Island’s premier sailing race. 

At noon on a Thursday in late July, a series of warning horns, radio announcements and a trumpeted fanfare emanated from a two-story anchored barge, along with the dropping of a flag. Then, the first group of vessels, driven by the wind, headed for the starting line, aiming to cross exactly at 12:05 p.m.

The Sea Cliff Yacht Club’s 46th Around Long Island Regatta was underway.

The regatta, which attracts serious racers and casual sailors alike, began in 1977 with 88 sailing yachts. Since then, it has developed a passionate following, despite the rigors of the race. 

The race is at least 207 miles long, starting east along the South Shore  to Montauk and then west along the North Shore to Hempstead Harbor. But tacking against headwinds or maneuvering to take advantage of stronger breezes usually adds dozens of miles. While some boats finish in under a day, a few straggle in almost three days later. And, as is always the case, some will drop out because of mechanical failure or too much or not enough wind.

“It's a mental and physical and equipment challenge,” said John Stephenson, 64, of New Paltz, who said he has competed in the regatta since 2006. “It’s a nonstop race, so the crew is active for anywhere from 36 to 60 hours with the mental challenges of driving through storms, sailing at night, being overtired, hallucinating, trying to make good decisions. We’ve had all kinds of weather, everything from storms to fog, not enough wind, too much wind, too much heat, not enough heat.”

71 VESSELS

This year, the race was held from July 27-30. A total of 71 boats competed in nine divisions grouped by size, hull type, sail configuration and boat speed. The boats generally must be at least 24 feet long, and there is no upper limit. The biggest boat this year was Kodiak, a 66-foot-long vessel from the U.S. Naval Academy.

The regatta requires a lot of work by a lot of volunteers to pull off.

“This is about a 10-month-long process,” said Shana Spanier-Ciniski, 58, of Glen Cove, who has co-chaired the race for two years. Her committee is comprised of 20 club members, including her son William Ciniski.

One club member found himself unexpectedly on the race committee this year. Harvey Bass, 76, of Sea Cliff, who said he has competed about 15 times and planned to do so again, but a fuel tank problem delayed launching his boat.

Bass, who created the Ranger Sailing Foundation in 2015 to sponsor children who can’t afford to participate in the yacht club’s junior sail training program, said he has sailed in the race about five times since 2007, with recipients of his scholarships serving as crew.

The first year, he said, “They ran the boat the whole race, and we got a second place.”

It hasn’t always gone so smoothly.

“We had a horrible experience in the 2009 race because the seas were huge,” Bass said. “I think only 11 boats finished the race.”

The crew’s parents had supplied food for the boat, including lasagna, which Bass said the kids started eating as they headed down the East River toward the race start. With the rough surf, well … it didn’t end well.

“We wound up turning back,” he said.

WHALES, SHARKS, DOLPHINS

This year’s race was thankfully less eventful, though it still had its share of difficulties.

As a 15-mph breeze blew up through the Narrows — the strait between Staten Island and Brooklyn — on the first day, boats from as far as Annapolis, Maryland, headed for the Verrazzano-Narrows Bridge and then for a buoy off the entrance to New York Harbor, where they could turn east and take full advantage of the southwest wind. They had a long, straight shot to Montauk and then up around the North Fork and down the Long Island Sound, where the winds are often light and unpredictable, to the finish in Hempstead Harbor off the Sea Cliff Yacht Club.

“The exit from New York Harbor was a real nice ride,” said Stephenson, who is chasing the record set by the late South Shore sailor Rudi Harbauer for sailing in the most consecutive regattas. Harbauer competed in the first 25 races.

Stephenson’s first three times in the regatta, from 2006 through 2008, he crewed for another yacht club member. The support engineer for IBM has since helmed his own boat, A Boy’s Dream, a 28-foot Laser 28 that he keeps in Kingston, New York. It is one of the smallest boats in the races.

“We actually made the trip when they canceled the race in 2020 during COVID just because we didn't want to break our streak,” he said. “So we went around the Island that year anyway.”

Out on the ocean this year, Stephenson said, “The wind kept building so we had to switch sails a few times.”

By the second morning, the boat was off Shinnecock Inlet. “We saw some whales. I saw sharks and dolphins.”

That night, he said, “We had lightning and a squall.”

On the Sound, he said, “The wind was pretty light Saturday morning until around noon, and we finally picked up a real nice breeze.”

Stephenson finished in 52 hours and 49 minutes for fifth place in his division.

UNEVEN SEAS

Josh Reisberg, 42, a lawyer from Sea Cliff and member of the yacht club, planned to take his 40-foot J-120 named Abilyn on the race double-handed — aka, with two sailors — with fellow yacht club member Mark DiSanti, but the boat was struck by lightning and damaged before the race. So he competed in his third regatta on another boat, a 34-foot Figaro 3 named Celeritas, with skipper Vlad Shablinsky and two others, including 17-year-old Sea Cliff Yacht Club junior sailor Annika Kaelin. None of them had sailed together before the race.

Along the South Shore, Reisberg said, “We hit average speeds of 16 knots while surfing. Waves were breaking over the boat. It was glorious!”

But then, he said, “The leg back home in the Sound was a test of patience. We had just enough wind to ghost over the finish just past midnight.”

The race took them 35 hours and 25 minutes for a fourth-place finish in their division.

Iris Vogel, 66, of New Rochelle, meanwhile, competed for the first time with a crew of six junior sailors ages 15 to 17 from the Huguenot Yacht Club. They sailed on a 30-foot J-112 named The ROCC, in honor of a deceased friend, Rocco Campanelli.

“The juniors handled the rough weather very well, this being their first time offshore,” she said.

The ROCC’s elapsed time was 39 hours and 16 minutes, for seventh in its division.

'A GREAT GROOVE' 

Brad Dickson, of Glen Cove, a former regatta co-chair, competed in the race as a first-time skipper after four competitions as a crew member. The manager of the Nassau County Public Works Department’s vehicle fleet sailed with a crew of relatives on Rhapsody, a 46½-foot Sabre that he and his wife bought last year.

“We had a great start,” said Dickson, 54. “Once under the bridge, the boat got into a great groove and handled the large seas amazingly well.” They continued to make progress — until the wind died for more than six hours off Northport.

Dickson placed second in his division with an elapsed time of 44 hours and 51 minutes.

Madelyn Ploch, a first-class midshipman, or senior, at the U.S. Naval Academy, was not so lucky.

Ploch was captain of the school’s Wahoo, a Kerr 50 with 14 people aboard. Once underway, they were averaging more than 17 mph before the Wahoo had to leave the race at Montauk. A crew member had fallen overboard while dousing a spinnaker — a large, kite-like, triangular sail at the bow of the boat — and received 10 stitches after being transferred to shore by a U.S. Coast Guard vessel.

The oldest boat in the race was a wooden yawl — a type of two-masted sailboat — named Golden-Eye, which was built in 1937 and is owned by construction company owner Michael Emmert, 45, and his father Richard, 81, both of Glen Head.

Richard Emmert bought the boat in 1972 and they entered the regatta in 2003 but did not finish, his son said. They have competed 12 times with Golden-Eye since 2009, he said. "She's quite competitive,” Michael Emmert said before the start.

He wasn’t wrong. “We came out of the start like a rocket,” Michael Emmert said, hitting 13 mph. Golden-Eye finished second in its division in 46 hours and 47 minutes.

67-HOUR CRUISE

When the last boat, Nomad, a Hunter 45 owned by Shane Haas, of Westchester, crossed the finish line at 7:44 a.m. on July 30 — 67 hours after starting — 50 of the 71 boats had completed the race.

“That’s pretty much typical,” said principal race officer Doug Wefer. The withdrawals were attributed to too much wind, not enough wind, mechanical problems and the Wahoo’s medical emergency.

The first boat to finish was the Naval Academy’s Kodiak, in about 27 hours. The overall winner after applying the handicapping (to compensate for slower boats and make the race more competitive) was Group 5, a 34-foot Figaro 2 sailed by a team of four students from Webb Institute, the naval architecture and marine engineering college in Glen Cove.

“The overall conditions were the full spectrum,” Wefer said of the race. “Quite a windy day on Thursday, to being becalmed on Friday, and just a glorious ride home for the last boats on Sunday.”