Passengers get on board on the Waterfront Center’s oyster sloop...

Passengers get on board on the Waterfront Center’s oyster sloop Christeen for the sunset cruise in Oyster Bay. Credit: Marisol Diaz

On sailboat cruises from Oyster Bay to 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 in Oakdale. 

Here's how to get a taste of cruising on Long Island's waters, whether destined for a swimming hole or merely a photo-worthy sunset.


ABOARD Layla, a 45-foot sailboat docked in Greenport

WHEN May 15 to Oct. 15 

INFO 631-319-0161,

Capt. Liz Gillooly leads up to six passengers on private sails from Greenport that explore the waters around Shelter Island. Options include shorter morning and sunset sails (from $750) and traditional half-day charters. Guests may bring their own snacks and drinks.


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

WHEN | WHERE 6 p.m. most days through Labor Day ($55-$75 a person) from 1 West End Ave., Oyster Bay, reserve online. The center offers other sailing experiences, including a two-hour harbor tour ($45-$65 a person), marine ecology cruises ($50 a person). Private charters available (starting at $1,250).

INFO 516-922-7245,

The view includes Gold Coast mansions lining tony Centre Island on cruises aboard the 40-foot sailboat. A U.S. Coast Guard-certified captain helms the ride through Oyster Bay Harbor and Cold Spring Harbor. You’ll learn about the history of Christeen, built in 1883 in Glenwood Landing and a National Historic Landmark since 1992.


ABOARD The Mon Tiki fleet of catamarans in Montauk 

INFO 631-668-2826, 

The 65-foot Mon Tiki Largo, the 40-foot Mon Tiki and the 26-foot Mon Tiki 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 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 on a two- to three-hour private sail (starting $250) through early October, and there's plenty of time to take a plunge into the water from the vessel's swim ramp and paddleboards (life jackets provided).


ABOARD Priscilla, a restored 1888 oyster sloop from the Long Island Maritime Museum in West Sayville

WHEN | WHERE 4 p.m. Tuesdays-Thursdays, $45 ($20 kids) or dinner sail 4 p.m. Fridays, 1 and 4 p.m. Saturdays-Sundays ($75 includes $30 food voucher), reserve online. Arrive 30 minutes before sail time at the dock behind The Snapper Inn restaurant, 500 Shore Dr., Oakdale.

INFO 631-854-4974,

The Long Island Maritime Museum's historic oyster sloop Priscilla hosts two-hour cruises on the Great South Bay. Some sails have included options for lunch or dinner at The Snapper Inn restaurant in Oakdale. Sails include plenty of narration that covers the ship's history among a 500-boat fleet that plied the South Shore bays for oysters. The vessel was retired in the 1960s and restored in 2002. It became a National Historic Landmark in 2006.


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