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Long Island sailing tours in Oyster Bay, Oakdale and Montauk

The executive director of the Waterfront Center in Oyster Bay, David Waldo, talks on July 14, 2015, about the sunset sail offered on the historic sloop Christeen, where its captain, Pete Macandrew, discusses the boat's history. (Credit: Newsday / Chris Ware)

On sailboat cruises from Oyster Bay, Oakdale and Montauk, you can relax on deck, cooled by sea spray and a glass of wine. Or you can get up off your cushion and join the hands on deck.

Here are three ways to sail into the sunset, to a swimming hole or a waterfront restaurant on a Long Island summer day.


ABOARD Priscilla, a restored oyster sloop from the Maritime Museum

WHEN | WHERE 1 and 4 p.m. Fridays, Saturdays and Sundays, $75 (includes $30 voucher for a meal at the Snapper Inn), $20 ages 12 and younger. Sailing only tour 4 p.m. Tuesdays-Thursdays, $45 ($20 kids). Arrive 30 minutes before sail time at the dock behind The Snapper Inn Restaurant, 500 Shore Drive, Oakdale.

INFO 631-854-4974,

Steering the oyster sloop Priscilla through choppy Great South Bay waters was a sea change for retired science teacher John Pesek, 68, of Mount Sinai. Pesek, who volunteers with the United States Coast Guard Auxiliary in Port Jefferson, was among the passengers who accepted Capt. Jim Romaine’s invitation to take the wheel and steer the Priscilla on a recent two-hour cruise.

“You’re much more in tune with the wind, the waves, and you’re much more affected by things like the current,” Pesek said after his turn at the wheel.

After running the engine from Oakdale to the mouth of the Connetquot River, the crew switched to wind power by raising the canvas. Romaine stood on deck and talked about the Priscilla’s past — illustrated with props such as a giant Blue Point oyster.

Until the Hurricane of 1938 led to the destruction of the local industry, “this boat was part of a 500-boat fleet that plied the South Shore bays for oysters” and sent such juicy bivalves across the Pond to customers such as British monarch Queen Victoria, Romaine said. After retired from oystering in the 1960s, the Priscilla was donated to the museum and restored in 2002, he said.

Linda Orlando, 65, of Mount Sinai, a retired Selden middle school teacher who also took the wheel, declared, “I never realized how difficult it is to sail a ship.”


ABOARD Christeen, a restored oyster sloop from The WaterFront Center in Oyster Bay

WHEN | WHERE 6 to 7:45 p.m. select Tuesdays, Wednesdays and Thursdays through Aug. 29 ($35 a person) from 1 West End Ave., Oyster Bay. The center offers other sailing experiences, including a two-hour harbor tour on select weekends

INFO 516-922-7245,

The view includes Gold Coast mansions lining the tony Centre Island on cruises aboard the 40-foot sailboat. A United States Coast Guard-certified captain helms the ride through Oyster Bay Harbor and Cold Spring Harbor, said David L. Waldo, executive director of the WaterFront Center. “You can help hoist the sails” or “ask to drive the boat,” Waldo says. You’ll also learn about the floating, National Historic Landmark built in 1883 in Glenwood Landing.


ABOARD The Mon Tiki fleet of catamarans in Montauk 

WHEN | WHERE Daily trips include a three-hour (11 a.m.-2 p.m.) sail and swim trip ($95-$105/adults, $65-$80/younger than 12) from Gurney’s Star Island Resort & Marina, 32 Star Island Rd., Montauk

INFO 631-886-4645,

The 65-foot Mon Tiki Largo, the 40-foot Mon Tiki and the 26-foot Montiki Mini — all catamarans — are playfully named after explorer Thor Heyerdahl’’s Kon-Tiki.

Amelia Ryan, who owns and operates the line with her husband, Capt. David Ryan, says the cruises explore a world beyond the currently chic resort community. “All of that falls away when you are out on the water with the sounds of the wind, the waves and the natural beauty,” which occasionally includes dolphin sightings, Ryan says. Passengers can bring their own lunch and beverages and there's plenty of time to take a plunge into the water from the vessel's swim ramp (life jackets provided).


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