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Popular Sailing, Catamaran & Gulet Tours Charters in Long Island  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sailing, Catamaran & Gulet Tours in Long Island- BoatBooker

Long Island

Long Island, United States

long-island

The world’s fastest sailing catamarans (F50s) are descending on New York Harbor, flying over the water at speeds exceeding 60 mph. While thousands fight for a glimpse from crowded shorelines, you could be sitting in the front row.
Why take a Private Boat Charter to SailGP?
Front-Row Access, No Crowds: Skip the packed spectator ferries and grandstands. Our private boat positions you at the innermost edge of the public boating boundary, offering unparalleled views of the race.

United States

Eva Grace: Bachelorette Party, Sunset Cruise

Middletown Township

Experience luxury and adventure aboard the stunning Eva Grace, a 2015 Jupiter 30&rsquo; Center Console, offering the perfect blend of performance and comfort. Based out of Middletown Township, this vessel comfortably accommodates up to six guests, making 

Set sail on a 2-hour eco-friendly sailing adventure from Westbrook, CT, where the scenic Long Island Sound becomes your playground. Glide silently across the water as you learn about local marine life and coastal ecosystems, with the chance to spot seabirds, seals, and more.

Joyride Charters

Westbrook

Come Sail with Captain Joy! Looking for an unforgettable experience on the water? Step aboard with Captain Joy &mdash; a USCG Master Captain with 40+ years of sailing adventures across the globe. Now docked in Westbrook, CT, she&rsquo;s ready to share the

Sail Long Island's Gold Coast on WINDSWEPT, a beautifully kept Jeanneau 36i! Private sailing charters can accommodate up to 6 guests. Departure times are flexible - select a start time that works best for your group!

Two-hour charters allow enough time to sail to the mouth of Oyster Bay Harbor and back. Perfect for catching a sunset or for touring the harbor, you'll have great views of the sandy bluffs and waterfront mansions that line the bay.

Windward Sailing Charters

Oyster Bay

Sail Long Island&#039;s Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i. Moored in Oyster Bay Harbor, she features a large shaded cockpit with cushions and ample room for 6, a secured deck with double lifelines and USCG-approved s

Set sail on an unforgettable 8-hour Mamaroneck adventure, where your departure time is completely up to you. Enjoy a relaxing sailing tour filled with scenic coastal views, a fresh sea breeze, and plenty of time to unwind or explore at your own pace. Whether you’re looking to soak up the sun or simply cruise in style, this flexible experience is tailored to your perfect day on the water.

Charter Nirvana

Mamaroneck

Step aboard Nirvana, a timeless 38&rsquo; Pearson 386 sailing yacht, and experience the beauty of Long Island Sound without the crowds, just you, your guests, and the open water. Departing from scenic Mamaroneck Harbor, your private charter is fully custo

All our trips can be customized! The base price is $200/hr with a 3-hour minimum. If you'd like to sail for longer or start at a different time, just let us know.
Enjoy sailing through New York City waters with stunning skyline views of Manhattan, the Statue of Liberty, and the Brooklyn Bridge. Perfect for sunset cruises (depending on timing), swimming stops, relaxing sails, and unforgettable proposal & engagement trips. Bring your own vibe- romantic, fun, or chill- and we’ll make it happen on the water.

North River Sailing –  Tantara

New York City

We&rsquo;re setting sail across Long Island Sound this season from our home base on historic City Island. With its network of islands, lighthouses, sheltered harbors, and classic coastal towns, this area offers one of the most scenic and rewarding sailing

Set sail with us on your two-hour private sailing charter of New York Harbor. Your boat tour will take in the sights of the Statue of Liberty, Ellis Island, Governors Island, and the Freedom Tower, to name a few. Our daytime boat tour is ideal for visitors to NY, friends to enjoy an outing, or families looking for something off the beaten path to enjoy in New York City.

Tribeca Sailing

Step aboard Tribeca Sailing, a beautifully restored 1964 Hinckley Pilot 35, and experience New York City from the water aboard a true classic. Combining timeless craftsmanship with modern comfort, this elegant sailboat accommodates up to six guests and of

Sunsets,  celebrations,  or just a get away.
USCG Licensed Captain with a lifetime of sailing experience and  local knowledge to plan a great trip from Stamford, CT.

Want to get out on the water? 

Custom arrangements can be made - just ask. 

?Come sail away!?

Gypsy Soul Tours

Stamford

Gypsy Soul Tours offers private, custom sailing charters from Stamford, Connecticut, delivering unforgettable experiences on the scenic Long Island Sound. Step aboard a beautifully maintained 2005 Beneteau Oceanis 373, a comfortable and spacious sailing y

Sailing, Catamaran & Gulet Tours in Long Island

Top Sailing, Catamaran & Gulet Tours in Long Island