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Five Sailing Excursions to Take on Long Island

Book a fun day on a sailboat on the waters around Long Island.

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The Ginny Marie Schooner. Photo: The Ginny Marie Schooner Facebook page.

Most people think of sailing excursions when they’re vacationing on a tropical island somewhere but there are plenty of places to hop aboard a sailboat to enjoy a day on the water right here on Long Island. Below we found just five of the many sailing charters you can book close to home.


Nautical Dreamer Sailing Charters - The Nautical Dreamer II is a Beneteau 50 sailing yacht that leaves out of Greenport Harbor. Choose from full day to 2-hour cruises. Overnight stays, weekends, and custom trips are also available. Location: Brewer Yacht Yard, Greenport Harbor, (631)767-0149.


Sailacat - A catamaran, Sailacat's charter boat offers private sail charters, sunset sails and boat tours in Historic Sag Harbor. Available for 4-hour sails with a beach break and swim time on weekends. They offer 2-4 hour sails midweek. Location: Sag Harbor, (631) 682-8288.


The Ginny Marie Schooner - The Ginny Marie is a 38’ wooden schooner that goes out of Port Jefferson Harbor. It’s historic, old world sailing that is a little romantic and a lot of fun. She can take up to 6 people on private charters that run 10am, 1pm, 4pm, and 6pm daily. Location: Harborfront Park, Port Jefferson, (631) 223-9180.


MTK Cruises - Offering three different vessels, MTK Cruises has Tomoka, a 40’ pontoon boat and two 27’ sailing catamarans, the Eleanor’s Pearl and the Calvin John. The pontoon can accommodate up to 33 people and the catamarans up to six. Each vessel can go to their 20’ water trampoline for a private gathering on the water or just cruise and relax. Location: 59 Star Island Road, Montauk, (631) 668-8079.


Layla Sailing - A 45’ sailing yacht available to take private charters of up to six people at a time. They offer morning, half-day, full-day, and sunset sails. The Layla is female owned and operated by Captain Liz. Location: 1410 Manhanset Ave, Dock H4, Greenport, (631) 319-0161.