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Sailing lessons offered at Oakcliff of Oyster Bay

Oakcliff Sailing Center is an elite training center for athletes who wish to compete in the Olympics, the America's Cup and other competitions. But the center also trains local people to sail, as demonstrated on June 29, 2016. (Credit: Newsday / Chris Ware)

Hobie Ponting spends most Tuesday, Wednesday and Thursday nights shouting at sea. The seemingly peculiar pastime is actually a requirement of his job and one revered by the mostly rookie sailors aboard his vessel.

Perched on the side of a Match 40 racing boat one Wednesday evening in late June, Ponting yells a warning:  “We’re about 10 seconds from a jibe,” he says, referring to a sailing maneuver used to turn the stern so the wind direction shifts from one side of a boat to the other.

Moments later, Ponting instructs his team to “prepare to tack” or align with the wind.

Susan Fredericks and Eric Roth are among five students who rush forward to the bow of the boat. Fredericks and Roth represent the diverse student body at Oakcliff Sailing in Oyster Bay, where many say they have gained an appreciation for, and greater understanding of, a water sport they long admired. Fredericks and Roth are supporters of the school, which qualifies them for once-a-week sailing lessons aimed at helping former landlubbers get their sea legs.

Fredericks, of Northport, enrolled in Oakcliff’s sailing program three years ago and never looked back — unless it was to track her competition during an evening race. Roth, meanwhile, has sailed for 30 years, but only joined Oakcliff in 2015.

“What’s attractive about sailing is it’s an extreme challenge that you’re never going to perfect,” says Roth, 52, of Plainview.


It is common practice for students to compete against each other while taking instruction from a coach during a sailing lesson. A Long Island native, Fredericks grew up riding on sailing vessels, but never learned how to steer or work the lines.

“I’m making the transition from cruising to racing,” says Fredericks, 65. “It can be terrifying at times, but when you come off the boat, it’s rewarding when you’re able to say, ‘I did that.’ ”

Oakcliff’s students are given access to the training course after making a minimum donation of $500 to the nonprofit school. Its high-performance training center includes intense on-the-water drills and a boat shop apprenticeship. Enrollees learn and assume all the roles aboard a ship. Students are trained by coaches and competitive sailors like Ponting, who has raced in several high-profile offshore events in the transatlantic. Ponting was once an Oakcliff student himself, having completed the Sapling program for advanced sailors in which he learned how to compete on high-performance racing boats and yachts such as 49ers, Nacra 17s and 470s. The Sapling program comes with the opportunity to compete in the Newport-Bermuda race.

Oakcliff is no stranger to sailing standouts. Its executive director, Dawn Riley, was the first woman to manage an America’s Cup sailing team in the head-to-head race dating back to the 1850s where crews battle for an international sporting trophy.

Oakcliff’s primary focus is to advance American sailing programs, according to Scott Guinn, the school’s public relations director. Despite their recommendation that students have some sailing experience before taking a course, students say between the one-on-one mentoring and support from shipmates, there is no shortage of information readily available.

Says Guinn, “Anyone can be a sailor in this program, as long as you like water.”


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