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

Sunset & Dinner Cruises 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.

Drift into a breathtaking afternoon cruise, where golden hues paint the sky and the sun melts into the horizon, creating an unforgettable sunset on the water.

United States

Rockaway Charters

New York City

Set sail on a luxurious and unforgettable adventure with Rockaway Charters, a 1999 Luhrs 36 Open Sportfishing boat that has been meticulously restored in 2024 for your comfort and enjoyment. Based out of vibrant New York City, this sleek vessel accommodat

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.

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

Enjoy a smooth and relaxing cruise through the calm, protected waters of Jones Inlet as you take in another breathtaking sunset. It's the perfect way to unwind and soak in the beauty of the evening.

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

Set sail on a 3-hour sunset tour and watch New York transform as day turns to night. Glide across the harbor past the Statue of Liberty and beneath the city skyline, glowing in golden light. Sip your favorite drink, feel the evening breeze, and take in panoramic views of iconic landmarks as the sun sets over the water — a perfect mix of relaxation, romance, and unforgettable scenery.

Karen Ann Charters

Karen Ann Charters offers an unforgettable on-the-water experience aboard a well-maintained 2000 Parker 28 Center Console, departing from the heart of New York City. Designed for comfort and performance, this spacious vessel accommodates up to six guests 

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

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

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

Sunset & Dinner Cruises in Oyster Bay

Top Sunset & Dinner Cruises in Oyster Bay