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

Boat & Yacht 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.

The Seaspray is the perfect mid-sized party boat, ideal for family gatherings, bachelor and bachelorette parties, birthdays, gender reveal celebrations, and even sea burials. You’re welcome to bring your own food, or we can handle catering for you.
We also offer a pet-friendly experience, so feel free to bring your furry friends along! Enjoy the vibe with our Bluetooth stereo system, ensuring great tunes for every occasion.

United States

Seaspray

Freeport

Step aboard Seaspray, a beautifully restored 1992 SULLIVAN Chesapeake Deck boat, now updated in 2021 to ensure an exceptional cruising experience. Based in Freeport, this spacious vessel accommodates up to 30 guests, making it the perfect choice for group

We offer three time slots each day, each lasting 3 hours. I've included everything you need. We bring along a great selection of water toys for your group to enjoy—stand-up paddleboards, kayaks, a small speedboat for tubing or waterskiing, plus large 15-foot inflatable docks and floats for lounging and swimming.
We typically meet in Oyster Bay and cruise the local waters before anchoring to enjoy swimming, relaxing, and a variety of water sports.

Long Island Yacht Rentals – Tranquility

Yacht rental includes watersports. Step aboard Long Island Yacht Rentals, a luxurious 2001 Carver 466 Motor Yacht, beautifully restored in 2025 and based in scenic Oyster Bay. With room for up to 12 guests, this spacious vessel is perfect for unforgettabl

We offer private ash scattering ceremonies in the legal waters of the Atlantic, accommodating up to 6 passengers in accordance with state and federal regulations. The trip lasts approximately 2 hours and provides a peaceful setting to honor your loved one. Please message us to schedule a date and time that works best for you.

Carolann P Fishing Charters

Carolann P Fishing Charters is a beautifully restored 1998 Luhrs 31 Sportfishing vessel (restored in 2025), based in Freeport, offering an unforgettable maritime experience for up to six guests. Powered by twin 315 HP Yanmar diesel inboard engines, this b

Experience the magic of Northport Harbor with our 2-Hour Sunset Cruise, the perfect way to unwind as the sun dips below the horizon. Enjoy stunning coastal views, peaceful waters, and local landmarks on this unforgettable sunset cruise and sightseeing adventure.

Sea Dog Cruising

Northport

Experience unforgettable adventures aboard Sea Dog Cruising, a beautifully maintained 2006 Atlantic Boat Company Duffy 35 Downeast, proudly based in Northport. Perfectly designed for up to six guests, this elegant vessel combines classic charm with modern

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

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

Want a relaxing day with family? Book a beach day with us. We anchor up at a private beach(only accessible by boat). The captain sets up floating rafts, docks, and lounge chairs. Kids want to play in the sand?
We have you covered. We anchor close enough that the kids can walk through the water to get there. Looking for a day with your friends to let your hair down and party? We break the music out and run well into the night.

GO With The Flo Charters

Wantagh

GO With The Flo Charters is a beautifully restored 2001 Pursuit 3070 Offshore Center Console (refit in 2026), delivering the perfect mix of performance, comfort, and reliability. Departing from Seaford, this versatile vessel welcomes up to six guests and 

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

Enjoy a relaxed 2-hour sunset cruise through Norwalk Harbor and around the Norwalk Islands. Perfect for couples or small groups looking to unwind and take in the views as the sun sets over the Sound.
The trip runs on a classic SeaCraft center console with a smooth ride. Seating is casual, with comfortable bean bags on deck so you can stretch out and enjoy the cruise.
Coolers and water are provided. Feel free to bring your own drinks and snacks.

Private trip for up to 3 guests. Simple, easy, and great!

Viking Fly Charters

Norwalk

Viking Fly Charters is a classic 2008 SeaCraft center console based in Norwalk, offering private, customizable trips for up to 3 guests. Powered by a reliable 140 HP Suzuki outboard, the boat cruises comfortably up to 33 knots, making it perfect for explo

All aboard for 4 hours of calm waters, marshes, and waterfront home views. Captain Ryan will take you and your group on a relaxing cruise inside the bay. The boat will have a large cooler with ice on board and the speakers ready to connect via cable or Bluetooth. 

***START TIME CAN BE ADJUSTED AFTER BOOKING***

“Bring Your Own” - Canned Alcohol Allowed (No Glass, No Red Wine)

Trip time will begin and end at the dock. We will do a 4-hour cruise around Island Park, Long Beach, and Hewlett Area.

Cast Net Charters

Island Park

Step aboard &ldquo;GO FISH&rdquo;, a 1987 Pursuit 2550 Center Console Cuddy Cabin operated by Cast Net Charters and based out of Island Park&mdash;perfect for unforgettable days on the water for up to 6 guests. Powered by a reliable 300 HP Suzuki outboard

Enjoy a 4-hour boat tour from Port Washington, New York, with stunning views of the NYC skyline. Cruise past iconic landmarks including the Statue of Liberty, Ellis Island, Governors Island, the Brooklyn Bridge, and the Manhattan skyline. Relax on the water, take in unforgettable scenery, or anchor in a peaceful spot to swim, sunbathe, and enjoy quality time with family and friends. A perfect blend of sightseeing and relaxation on the water.
$875 per hour. 4-hour minimum. Departure times can be arranged.

Osca Yachting

Port Washington

Step aboard the 2025 Galeon 560 Fly and experience New York Harbor like never before. This 56-foot luxury flybridge yacht is designed for up to 13 guests, offering the perfect setting for private charters, sunset cruises, swimming trips, and unforgettable

Boat & Yacht Tours in Oyster Bay

Top Boat & Yacht Tours in Oyster Bay