Be Part of Sailing History: Around Long Island Regatta in spectacular New York Harbor, July, 2021

We are sorry to announce:

2020 Around Long Island Regatta Cancelled

 See News Item Below for Coronavirus Related Update

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TBA:  July , 2021

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July , 2021
Final entry deadline

 July , 2021 
Captains' Meeting - Liberty House, Liberty Landing Marina, Jersey City, NJ




July , 2021 
Start of the 44th Around Long Island Regatta in spectacular New York Harbor!

July , 2021 
Awards Ceremony & Beach Party
Sea Cliff Yacht Club, Sea Cliff, NY

Around Long Island Regatta in the News

From the 2020 Around Long Island Regatta (44th Annual) event:

Hello Friends - We hope this finds you well and enjoying the summer, as best you can, in this unique year.

Unfortunately, the Around Long Island Regatta Committee has made the difficult decision to cancel this year's ALIR. Many have written to say that they were looking forward to sailing this year but the challenges of running an overnight race during the COVID-19 pandemic are too great and with only a month to go we think it only fair to now make a decision so that people can make alternative plans.

The ALIR committee will miss welcoming all the competitors to Sea Cliff Yacht Club over the weekend of July 24-26 but we will soon be meeting to plan the 44th running of the Around Long Island Regatta in 2021.

If you have paid your entry fee already, we will have your entry fee refunded promptly. For all of you, we hope you'll put the 2021 Around Long Island Regatta for late July, next year, on your calendar.

Have a safe and enjoyable summer of 2020!

Best regards,

James Aikman, Regatta Chairman
Around Long Island Regatta

Of the world class sailors that participated in the Around Long Island Regatta, a three-day race that ended in Sea Cliff on July 28, among them was 12-year-old resident Samantha Maynard, a five-year member of Sea Cliff Yacht Club’s junior sailing program. She was the youngest sailor from Sea Cliff Yacht Club that competed in this year’s regatta.

The race is designed for sailors of all skill levels running in as many as 10 divisions, and includes crews of weekend cruisers, blue-water competitors, Academy sailing teams, and even junior sailors like Samantha, sailing along a 205 nautical mile course.

“It’s a big deal to have to sail around Long Island without stopping,” said event co-chair Doug Wefer, of Glen Head.

For Samantha, who’s more accustomed to chartering single-person boats like optis (basic training boats) and lasers (more sophisticated trainers), the regatta was “not that hard.”

“It was easier than I thought it would be, but it was still challenging,” Samantha said, as she adjusted the white sailor’s knot bracelet that was unmistakably present against her tanned skin. “It was an adventure and something new that I enjoyed.”

For this year’s regatta Samantha joined Harvey Bass, a former commodore and member of the yacht club, aboard his ship the No No Nanette, rounding out his six-person crew. In 2007, he assembled the first junior boat of Sea Cliff sailors to compete in ALIR.

“That year all the juniors ran the boat and they wound up with a second place finish,” said Bass, of Sea Cliff. Over the years Bass has selected junior sailors to help man his 37-foot Hunter boat during the regatta in an effort to promote the love of the sport at a young age.

“What few people realize is that sailing is more than just sailing itself, because with young people it really teaches them a lot of other things,” he said. “You teach them how to get along with others because, especially on a larger boat, there’s a lot of cooperation involved.”

The regatta begins in New York Harbor and heads due east past Brooklyn and Long Island’s South Shore, before winding around Montauk, across Gardiner’s Bay, and then into the Long Island Sound before ending in Sea Cliff.

While aboard, Samantha was responsible for tacking, putting the bow through the eye of the wind, jibbing, putting the stern of the boat through the eye of the wind, and trimming, or adjusting the sails. Once the boat reared into the Sound she took charge of the some of the steering. She said the last leg of the course, a 30-mile stretch to the yacht club, was the most challenging, taking 17 and a half hours.

Samantha first learned that there might be a delay on Saturday morning. Emerging from below deck she was told that the Nanette had been stuck in the same spot since 2 a.m. “The wind was just dead the entire day,” she recalled. “It was so frustrating just not moving anywhere.” After sitting in no wind for 24 hours, the anticipation of crossing the finish line in Hempstead Harbor was something Samantha would never forget.

“Since I’ve never done the regatta, I never had this feeling,” she said. “The accomplishment was just great.”

Although this was her first year competing in ALIR, Samantha has raced in events sponsored by the Junior Sailing Association of Long Island Sound, which supports its member sailing programs through leadership, training, and programming. She admitted she finds greater difficulty sailing in the shorter races, which take place over the course of a few hours rather than a few days.

“With the races I do on my laser, I’m thinking every single second, like ‘where are the puffs of wind?,’ ‘where exactly can I go?,’ ‘how am I going to get around this mark?’” she said. “I’m constantly thinking about what I’m going to do on the course. The ALIR was shocking to me because you’re still always thinking, but it’s a slower process.”

Fostering an appreciation for the sport is part of Bass’s mission, and getting young sailors like Samantha out on the water “delivers on that mission all the way around,” he said.

For Samantha, sailing is her first love, and the yacht club is her “second home.” “Every single summer since I was seven I’ve been waking up, going to swim practice and then sailing all day long,” she said. “It’s been so nice. They teach us very well here.”

“It makes me a little more confident about what I can do in the future,” she added. Samantha hopes to pursue a dual career as a naval engineer and a patent lawyer so she can create unique inventions for boats and help the sailing community.

Wahoo added its name to the list of Naval Academy sailboats that posted impressive accomplishments this summer.

Skipper Matthew McClelland and his crew aboard the Ker 50-footer secured overall victory in the 43rd Around Long Island Regatta, which began on July 25. Wahoo wound up with a corrected time of 1 day, 13 hours, 12 minutes and 35 seconds – just over an hour better than a 39-foot entry fielded by the United States Merchant Marine Academy.

“We were ecstatic about the result. To end our month of sailing on a high note was very rewarding,” said McClelland, a Georgia native who also led Wahoo to second place in class for the Marblehead-to-Halifax Race.

The Around Long Island Regatta starts off the Statue of Liberty in the Hudson River then proceeds south through the Verrazano Bridge into the Atlantic Ocean and east along the south shore of Long Island. After rounding Montauk Point, the fleet heads westward into Long Island Sound to the finish inside Hempstead Harbor.

It is a 205-nautical mile passage featuring numerous challenges, including brisk tidal currents, hazardous shoals and often fickle winds.

As often occurs in this race, the wind shut off in the middle of the first night and competitors were forced to choose between staying offshore or hugging the beach in search of breeze. Wahoo opted to stay further offshore and was becalmed for a while.

Wahoo was one of two entries fielded by the Naval Academy Varsity Offshore Sailing Team along with the Reichel-Pugh 66 Zaraffa, which captured line honors with an elapsed time of 1 day, 8 hours, 42 minutes and 40 seconds.

Zaraffa led the fleet the entire way, but didn’t have as much wind as the trailing boats and therefore was not able to extend. A critical juncture of the race takes place around the midway mark when the fleet rounds Montauk Point.

Zaraffa skipper Sean Caraher chose to stay outside of the various land masses located in Long Island Sound in order to avoid foul current. Wahoo rounded Montauk Point about an hour later and elected to sail through what is known as Plum Gut.

“We hit the current just right and were able to sail a shorter distance than Zaraffa, which ultimately made a big difference,” McClelland said. “That was one important decision we got right.”

Winds became fluky upon approach to Oyster Bay and the Wahoo crew worked hard changing and trimming sails in order to make headway. Zaraffa crossed the finish line just after 2 a.m. on Saturday with Wahoo coming home about an hour and a half later. The Reichel Pugh 66 owed the Ker 50 almost four hours on handicap so that competition was easily decided.

“There were three times during the race when there was basically no wind so finding a way to keep the boat moving was crucial,” McClelland said.

Nick Walden served as navigator while Jonathan Hitt was executive officer on Wahoo, which had an elapsed time of 34 hours. Hitt and Katie Boyle were the primary drivers on their respective watches.

“Perseverance was the key when the wind shut off at the western end of Long Island Sound during the middle of night,” said Jahn Tihansky, head coach of the Navy offshore sailing program. “Those last 12 miles took about three hours, but the Wahoo crew pushed hard, changed sails as needed and kept their foot on gas pedal.”

McClelland and company had to wait until Saturday evening when several smaller boats finished to find out if their corrected time held up. M.A.T. 1180, a Mark Mills-designed 39-footer crewed entirely by Merchant Marine Academy midshipmen, was runner-up in fleet.

It was a banner summer season for the Naval Academy Varsity Offshore Sailing team, which also notched class victories in the Annapolis-to-Newport Race, Marion-to-Bermuda Race and Block Island Race Week. Zaraffa was previously overall winner of the Marblehead-to-Halifax Race.

“I’m proud as heck of the whole team across the board. Every crew brought home at least one trophy, which speaks to the depth of talent and quality of the program we have,” Tihansky said.

About ALIR

The Around Long Island Regatta, first run in 1977, covers a 205 nautical mile course combining ocean, harbor and open sound racing. The race’s 10+ divisions include sailboats 24 feet or longer and sailors at all levels who typically finish in one to three days. This unique race is for everyone – weekend cruisers, serious blue-water competitors, double-handers, academy sailing teams, even junior sailors. Racing yachtsmen earn points for the Northern Ocean Racing Trophy and other IRC distance trophies.

Considered Long Island's premier sailing race, the annual Around Long Island Regatta starts on a Thursday near the end of July just off Ellis Island in New York Harbor. The challenging harbor start and prevailing southerlies sets the boats tacking towards the Narrows and out into the Atlantic. The ocean leg parallels Long Island's south shore along Long Beach, Jones Beach, Fire Island, the Hamptons and on to Montauk. Some boats choose the shortest distance hugging the shore while others opt for deeper water in search of better wind.

After rounding Montauk Point, sailors must judge wind, tides and current as they head northwest to Plum Gut, where they hope a favorable current will flush them into the Long Island Sound. The final westerly leg is all about reading wind shifts and working currents to their advantage along Long Island’s north shore or the southern shore of Connecticut. The race ends in beautiful Hempstead Harbor at the Glen Cove breakwater.

The weekend concludes with the ALIR Awards Ceremony and Beach Party hosted by the Sea Cliff Yacht Club on Sunday afternoon. Trophies are awarded for the first three finishers in each division, with many additional awards for various categories. There is always music, food and drink, a welcoming Yacht Club crowd, and great sailing tales – some of which might even be true!

Contact Us

For More Information about the Around Long Island Regatta please send your inquiries to:


Sea Cliff Yacht Club Office - 516-671-7374
Regatta Desk 516-945-9209 (While Race In Progress)