Long Island Sailing and Boat Tours to Greenport, Oyster Bay, Oakdale and Montauk

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

Here’s how to taste cruising the waters of Long Island, whether it’s for a swimming hole or just a photo-worthy sunset on a summer’s day.


A BOARD Layla, a 45ft sailboat moored in Greenport

NEWS 631-319-0161, laylasailing.com

Captain Liz Gillooly leads up to six passengers on private cruises from Greenport that explore the waters around Shelter Island. Options include shorter morning and sunset sails (from $700) in addition to traditional half-day charters. Customers can bring their own snacks and drinks.


Passengers board the oyster sloop Christeen from the Waterfront Center for the sunset cruise to Oyster Bay.
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A BOARD Christen, a restored oyster sloop from the WaterFront Center in Oyster Bay

WHEN | OR 6 p.m. most nights through Labor Day ($45 pp) from 1 West End Ave., Oyster Bay, reserve online. The center offers other boating experiences, including a two-hour harbor tour. Private charters available ($985).

NEWS 516-922-7245, thewaterfrontcenter.org

The view includes Gold Coast mansions lining Tony Center Island when cruising aboard the 40ft sailboat. A United States Coast Guard-certified captain leads the ride through Oyster Bay Harbor and Cold Spring Harbor. Learn about the history of Christen, a National Historic Landmark built in 1883 at Glenwood Landing.


A BOARD The Mon Tiki catamaran fleet in Montauk

NEWS 631-668-2826, voilemontauk.com

The 65ft Mon Tiki Largo, 40ft Mon Tiki and 26ft 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, Captain David Ryan, says the cruises explore a world beyond the currently posh resort community. “It all goes away when you’re out on the water with the sounds of the wind, the waves, and the natural beauty,” which sometimes includes dolphin sightings, Ryan says. Passengers can bring their own lunch and drinks on a two- to three-hour private cruise (from $250) through early October, and there’s plenty of time to dive into the water from the ramp boat and the ship’s paddle boards (life jackets provided).


Cruises are available on the Priscilla sailboat in West Sayville.

Cruises are available on the Priscilla sailboat in West Sayville.
Credit: Benjamin Petit

A BOARD Priscilla, a restored 1888 oyster sloop from the West Sayville Maritime Museum

WHEN | OR 4 p.m. Tuesday-Thursday, $45 ($20 for children) or dinner at 4 p.m. Friday, 1 and 4 p.m. Saturday-Sunday ($75 includes a $30 food voucher), reserve online . Arrive 30 minutes prior to departure time at the dock behind The Snapper Inn Restaurant, 500 Shore Drive, Oakdale.

NEWS 631-854-4974, www.limaritime.org

Priscilla, the Long Island Maritime Museum’s historic oyster sloop, hosts two hours cruises on the Great Southern Bay. Some cruises have included options for lunch or dinner at the Snapper Inn restaurant in Oakdale. The sails include many narratives that cover the ship’s history among a fleet of 500 boats that plied the bays on the south shore for oysters. The ship was retired in the 1960s and restored in 2002.

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