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

Sunset & Dinner Cruises in Stratford, CT- BoatBooker

Stratford

Stratford, United States

stratford

Discover Stratford Boating Charters in a coastal town perfectly positioned for days on the water. Set where a major New England river meets Long Island Sound, Stratford offers a blend of calm, scenic waterways and open‑sound horizons that suit relaxed cruises, family outings, and adventure‑ready trips alike.Protected river channels are ideal for first‑timers and casual sightseeing, with winding coves, broad tidal flats, and salt‑marsh backdrops that often reward guests with coastal bird and wildlife sightings. Move seaward and you’ll find gentle reaches of Long Island Sound that are great for half‑day escapes, sandbar stops, and sunset cruises, plus wider routes for longer day trips along Connecticut’s shoreline.Anglers book Stratford boating charters for seasonal runs of inshore gamefish and the flexibility to switch between river and nearshore grounds as conditions change. Sightseers love the mix of historic waterfronts, classic New England vistas, and photogenic navigational landmarks. Kayak and paddleboard‑friendly coves, swim spots, and picnic‑ready beaches round out the options for groups seeking variety without long travel times.Whether you’re planning a private tour, a hands‑on sailing or powerboat lesson, or a full‑day exploration of nearby coastal towns, Stratford boating charters deliver smooth access, diverse itineraries, and memorable views throughout the season. Arrive with a sense of adventure, and let your captain tailor the route to the tides, the weather, and your crew’s pace.

Evening trip to the Thimble Islands to enjoy the Sunset!  (Grill, utensils, pans, two burner stove provided - you provide the food and cooking expertise!)

United States

Nightjack

Branford

Discover the perfect getaway on the water aboard Nightjack, a 2002 Levy 32sc Cruiser docked in Branford. This beautiful vessel offers ample space for up to six guests, making it an ideal choice for a day out with friends or family. Powered by a 330 HP Cum

We will head out about an hour before sunset on one of our local Rivers which will give us a chance to see some beautiful wildlife and scenic backdrops as we make our way into Long Island Sound where we will travel down the coastline and enjoy nature's beauty.

Rising Tide

Step aboard Rising Tide, a sleek 2017 Mako 21 LTS Center Console, perfect for an unforgettable day on the water. Based out of Milford, this well-equipped vessel accommodates up to three guests for a premium, personalized adventure. Powered by a 150 HP Mer

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

Oyster Bay

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

Unwind on a peaceful 2-hour Sunset Sail departing from Westbrook, CT, and experience the magic of golden hour on the water. As the sun dips below the horizon, enjoy stunning views of the coastline bathed in warm light and the gentle rhythm of the sailboat. It’s the perfect way to end your day on the Sound.

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

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

Enjoy a luxurious 4-hour yacht escape in Croton-Harmon NY, dinner prepared by a private chef and a customizable menu you choose before your trip. Sit back, cruise in style, and savor a freshly prepared meal while taking in the scenic coastline.

Dinner on a Yacht - the Hudson River

Croton-on-Hudson

Step aboard Gypsy Rose Yacht, a beautifully restored 1981 Cruisers Yachts VillaVee 288 Cruiser (fully renovated in 2025), and experience the thrill on The Hudson River. Designed for intimate outings of up to six guests, this classic cruiser blends timeles

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

Want to get out on the water? Come sail away!
Custom plans can be arranged; just ask.

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

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