Where to sail in New York City

Is your sailing knowledge limited to Popeye and Gilligan's Island? Join us for a firsthand account of sailing the Hudson blue.

Photographs: Roxana Marroquin

What drew me to sailing is probably the same thing that draws Jewish men toward golden shiksas—the mystic appeal of the WASP. The sport so beloved by preppies the world over has fascinated me for years. But like Woody Allen in Broadway Danny Rose, I’m something of a “landlocked Hebrew”: feeble muscle structure, a lack of expensive white linen clothing in my closet and an undeniably Semitic ancestry.

Even so, I decided to sign up for a basic keelboat course with the Manhattan Sailing School, which is the largest and most respected such organization operating in the New York Harbor. The course ($690 for either one weekend or five weeknights of instruction) runs out of the North Cove in Battery Park City.

Pre-sailing lecture
Boarding the Mermaid (MSS’s floating classroom and the location of a two-hour Friday evening beginners’ lecture), it became apparent that my vision of sailing—informed by Gorton’s fish stick commercials and Ralph Lauren ads—was a bit distorted. MSS likens its keelboat course to learning a language via immersive instruction, and it’s an apt metaphor. There’s a lot to take in, and the instruction may flow over you like ancient Greek. Happily, another MSS claim—everything will soon click into focus—is also true.

On the water
I arrived at 9am on Saturday morning and was introduced to Andrew Sarfaty, my skipper for the weekend, and the rest of our crew. MSS’s fleet consists of mostly J/24s (24-foot keelboats) named for historic ships. Ours, called the Swordfish, was out of the marina by 10:30am.

We spent the afternoon learning to tack (turning the bow through the eye of the wind), jibe (turning the stern through the wind), and man both the sheets (the lines that control the shape of the sail in relation to the wind) and the tiller (the wooden steering device that attaches to the boat’s rudder).

Instincts play a role, as does concentration on the shifting wind patterns. My hold on the latter was derailed as I scoped the view of Manhattan. This resulted in more than a few heels (a sharp but thrilling tipping of the vessel). We came in at 6pm and learned how to secure the boat in the port.

Day two was less rigorous, and my crewmates and I tested our new knowledge. Sarfaty proved a patient instructor, even as I pumped him for salty sailorspeak. Among the gems I picked up: Sailors call powerboats “stinkpots”; Sarfaty also praised the “gentlemanly breeze” (the opposite of a “stiff breeze”).

We spent a brisk late afternoon trading turns at the tiller. The weekend felt wonderfully long, and as healthy as a yoga retreat.

It wasn’t until we docked for the last time that Sarfaty revealed that I was the only student he’s had who wore a dress during on-water instruction. And I thought my Jewish mien would make me stand out.

Sail away

Strap on a life jacket and check out these other urban sailing schools.

Manhattan Sailing School (385 South End Ave #7G, 212-786-0400; sailmanhattan.com)
For serious city sailors, all roads lead to MSS. After basic sailing (see left), try a more intensive class like the overnight coastal cruising in the Atlantic Highlands ($690), or join the club for unlimited seasonal access to the fleet. Before pushing off, fuel up with a croque-monsieur ($8.50) at Financier Patisserie (World Financial Center, 3--4 World Financial Center between North End Ave and West St, 212-786-3220).

Hudson River Community Sailing (Pier 66 Boathouse, W 25th St at the Hudson River; 212-924-1920, hudsonsailing.org)
If you’re not all-in for a weekend course, HRCS offers a quickie alternative. The $60 Taste of Sailing seminar claims to cover boating basics in just two hours on the water. Postsail, walk east to the bar at the Red Cat (227 Tenth Ave between 23rd and 24th Sts, 212-242-1122) for a fried oyster salad ($14) and a cold Allagash White ale ($9).

Offshore Sailing School (Chelsea Piers, Twelfth Ave at 23rd St; 212-336-6666, offshore-sailing.com)
’Round the marina, we heard this club referred to as the “ivy league of sailing schools.” If that doesn’t activate your gag reflex, pop that polo collar and sign up: The three-day Learn to Sail course costs $895, but through August 1, the school is offering a special discounted rate of $590 for new bookings. Go modest come lunchtime, and try the goat-cheese sandwich ($8.95) at the nearby ’wichcraft (269 Eleventh Ave between 27th and 28th Sts; 212-780-0577, wichcraftnyc.com).

South Street Seaport Museum (12 Fulton St between South and Water Sts; 212-748-8786, southstreetseaportmuseum.org)
More experienced sailors can volunteer as active crew members aboard one of the South Street Seaport museum’s historic vessels, like the Pioneer. SSSM provides free, on-water training sessions for its crew, but there is a trade-off: a Coast Guard--mandated drug test, plus close proximity to tourists. On the weekend, gather some rations at the new Fulton Stall Market, located in the former fish stalls along South Street (fultonstallmarket.com).

Sail NY (Lincoln Harbor Marina, 1500 Harbor Blvd at Riverview Dr, Weehawken, New Jersey; 212-222-1406, sailny.org)
Seriously cut-rate alternatives to Manhattan’s costly sailing clubs come with some unfortunate fine print at Sail NY: The fleet is berthed in Weehawken—mere minutes from Manhattan, but located in New Jersey nonetheless. Low prices (basic sailing costs $325 and membership to the club is just $350 May through October) make trekking to the Garden State much easier to swallow. Pack a lunch at the Port Authority greenmarket (Thursdays 8am--6pm) before boarding the 156, 158 or 159 bus, which all stop in front of the marina.

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