Top 10 Boat Tours & Water Sports in Greenport, New York (NY)

Yachting adventures on the water on a variety of fully crewed sailing and powerboats.

With the help of Shaka Flyboarding you can harness some serious water power to experience a flight like no other. Call or text today for more info ⚓️✌ Strap onto the board, fire up a 260 hp personal watercraft with a hose attached to it and a powerful stream of water propels you 50 feet into the air. “Being on a flyboard is the closest you’ll ever get to being Iron Man,”

Feel the thrill and adventure sailing on newly built 52’ Virgin Star USCG certified for 47 passengers. Virgin Star is a large spacious trimaran offering a comfortable stable sail out to to hidden coves and bays of North and South Forks. Sailing daily from Preston’s Wharf in Greenport, NY offering daily harbor sails, Romantic sunset sails, Private Half Day and Full Day Charters.

GLORY, an environmentally-friendly vessel, has delighted adults and children alike with whisper-quiet and fume-free tours of the nooks and crannies of the Peconic Bay since 1999. GLORY takes visitors back to a bygone era with its classic lines and elegant mahogany and gold-plated trim as it glides along the bay.

Join us for the best day of summer! Allow Layla's crew to take care of your every need as we sail through the bays surrounding Greenport. Captain Liz earned her captain's license sailing in the USVI, Hawaii and even across the Atlantic Ocean. She brings this experience back to her hometown, to share her love with the sea with guests of all experience levels.

Paddle with One Love Beach on the beautiful North Fork of Long Island! You may choose to join our weekly Tuesday meet-ups or come on a weekend tour! We offer lessons for beginners, tours through the marshes and advanced clinics for racers! Come join our community of paddlers and see what the North Fork has to offer!

For an authentic, memorable North Fork adventure, sail Deliverance of Greenport, with Greenport's original windjammer, Cap'n Dan (since 1972). With the wind in the sails, the warmth of the sun and serenity, enjoy the scenery and protected waters of Peconic & Gardiner's Bays. The Hallock Family has been sailing these waters since 1640. We are well seasoned with local sea salt! Captain Dan is an 11th generation and has kept this tradition alive by building and sailing 8 different passenger vessels from #greenport. Old time sailing the way it was done in the days of working sail!

Nautical Dreamer is a 50' Beneteau sail boat. There are two bathrooms, kitchen, fridge, freezer, AC/Heat. and out side shower. We do 2hr, 4hr, Fullday, 2 hr Sunset and over night charters. You can sail the boat or not, this is an easy going laid back cruise. Just tell us what you want to do. Sail, swim sail some more.