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

Sailing, Catamaran & Gulet Tours in Oyster Bay, NY- BoatBooker

Oyster Bay

Oyster Bay, United States

oyster-bay

Discover why Oyster Bay, New York is a favorite for boaters seeking calm, scenic waters along the North Shore of Long Island. Sheltered coves and broad stretches of the Sound create ideal conditions for relaxed cruising, easy anchoring, and smooth sightseeing. With tree-lined shorelines, classic waterfront homes, and gentle breezes, it’s a picturesque setting for both first-time guests and seasoned captains.Oyster Bay boating charters offer a versatile way to experience the area. Choose a comfortable motor yacht for effortless coastal exploring, a nimble sailboat to catch the afternoon wind, or a center-console for a day of light tackle and on-the-water adventure. Families enjoy leisurely picnics on deck and swim stops in protected inlets, while couples love golden-hour cruises with sweeping views.Wildlife watchers often spot seabirds riding the thermals and occasional marine life in the quieter backwaters. Kayaks, paddleboards, and tenders add fun at anchor, turning serene bays into your private playground. On longer outings, skippers can follow the shoreline to discover new vistas and neighboring harbors, then return to Oyster Bay’s welcoming moorings before dusk.Whether you’re planning a half-day escape or a full-day charter, the combination of gentle seas, varied vessel options, and postcard-worthy scenery makes Oyster Bay boating charters a standout choice. Come aboard, set a relaxed course, and enjoy an easygoing Long Island adventure from the best seat in the house—the water.

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.

United States

Windward Sailing Charters

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 Oyster Bay

Top Sailing, Catamaran & Gulet Tours in Oyster Bay