Stratford Boat Tours

The best out of 16 boat tours in Stratford - enter dates to check availability

Stratford Boat Tours

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Top Boat Tours in Stratford

Stratford: 16 boats available

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21 ft
Up to 3 people
Rising Tide
Stratford
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.
trips from
US $200
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20 ft
Up to 3 people
Viking Fly Charters
5.0
/5
(5 external reviews)
Norwalk (15.4 miles from Stratford)
Viking Fly Charters is a classic 2008 SeaCraft center console based in Norwalk, offering private, customizable trips for up to 3 guests.
+1
trips from
US $295
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32 ft
Up to 6 people
Nightjack
Branford (26 min drive from Stratford)
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.
+1
trips from
US $550
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36 ft
Up to 6 people
Windward Sailing Charters
5.0
/5
(3 reviews)
Oyster Bay (1 hr 29 min drive from Stratford)
Sail Long Island's Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i.

"From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain." —⁠ Todd,
+5
trips from
US $525
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50 ft
Up to 13 people
Long Island Yacht Rentals – Tranquility
5.0
/5
(1 review)
Oyster Bay (1 hr 27 min drive from Stratford)
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.

"Captain Jeff was great, the boat was great, the water activities activities were great." —⁠ Joyce,
+1
trips from
US $1,800
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35 ft
Up to 6 people
One More Drift Charters
5.0
/5
(217 external reviews)
Clinton (41 min drive from Stratford)
Embark on a luxurious and unforgettable journey with One More Drift Charters, operating a beautifully restored 1989 Viking Convertible Sportfish, based in scenic Clinton.
trips from
US $795
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36 ft
Up to 6 people
Joyride Charters
5.0
/5
(1 review)
Westbrook (46 min drive from Stratford)
Come Sail with Captain Joy! Looking for an unforgettable experience on the water? Step aboard with Captain Joy — a USCG Master Captain with 40+ years of sailing adventures across the globe.

"Joy was an incredible captain for our fathers day evening sail." —⁠ Amy,
trips from
US $540
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37 ft
Up to 6 people
Gypsy Soul Tours
New
5.0
/5
(1 review)
Stamford (23.2 miles from Stratford)
Gypsy Soul Tours offers private, custom sailing charters from Stamford, Connecticut, delivering unforgettable experiences on the scenic Long Island Sound.

"We sailed with him out of Stamford on an unexpectedly windy day." —⁠ Kevin,
+2
trips from
US $750
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25 ft
Up to 6 people
Fire Island Fishing Charters
5.0
/5
(30 external reviews)
Ocean Beach (2 hr 33 min drive from Stratford)
Experience the ultimate day on the water with Fire Island Fishing Charters, a sleek and reliable 2017 Robalo 242 Center Console based in picturesque Ocean Beach.
trips from
US $650
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56 ft
Up to 13 people
Osca Yachting
New
Port Washington (38.5 miles from Stratford)
Step aboard the 2025 Galeon 560 Fly and experience New York Harbor like never before.
+1
trips from
US $3,750

Frequently Asked Questions about Boat Tours in Stratford

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Boating in 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.

What people said about boating in Stratford

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