Westbrook Boat Tours

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

Westbrook Boat Tours

16 boats available

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Top Boat Tours in Westbrook

Westbrook: 16 boats available

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Listing image
Sailing silhouette
36 ft
Up to 6 people
5.0
/5
(1 review)
5+ external reviews
Westbrook
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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Sportfishing silhouette
35 ft
Up to 6 people
5.0
/5
(201 external reviews)
Clinton (12 min drive from Westbrook)
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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Motor yacht silhouette
41 ft
Up to 6 people
Montauk (3 hr 33 min drive from Westbrook)
Experience timeless elegance and adventure aboard Montauk Venture Charters, a beautifully restored 1961 Hatteras Sportfish Motor Yacht, fully refreshed in 2020.
trips from
US $300
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Sportfishing silhouette
41 ft
Up to 6 people
4.9
/5
(12 external reviews)
Greenport (2 hr 4 min drive from Westbrook)
Step aboard The Blue Fin IV, a beautifully restored 1968 Custom Ray Chi Chi 41 Sportfish, expertly refurbished in 2019 and based in scenic Greenport.
trips from
US $750
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Cruiser silhouette
32 ft
Up to 6 people
Branford (25 min drive from Westbrook)
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
Listing image
Downeast silhouette
35 ft
Up to 6 people
Just listed
Groton (23.7 miles from Westbrook)
FV Kelly Marie Boat Cruises is a classic 2004 Terry Jason Lobster Downeast vessel, beautifully suited for comfortable and intimate private charters departing from Groton, Connecticut.
+2
trips from
US $400
Listing image
Center console silhouette
30 ft
Up to 6 people
5.0
/5
(19 external reviews)
Montauk (30.4 miles from Westbrook)
Experience Montauk from the water with a Grady-White 30 and enjoy a private charter designed entirely around your group.
trips from
US $600
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Cuddy cabin silhouette
28 ft
Up to 6 people
5.0
/5
(36 external reviews)
Montauk (3 hr 35 min drive from Westbrook)
Set sail with VitaminSea Voyages, a premium boating experience departing from the scenic shores of Montauk aboard a 2011 Steiger Craft Miami Cuddy Cabin.
trips from
US $450
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Motor yacht silhouette
53 ft
Up to 10 people
Sag Harbor (3 hr 5 min drive from Westbrook)
    Galeon 510 Sky Deck is a stunning 2019 Galeon 510 Sky Deck Motor Yacht (restored in 2025), available for unforgettable private charters from Sag Harbor.
trips from
US $3,200
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Headboat silhouette
50 ft
Up to 27 people
4.3
/5
(1 review)
Montauk (3 hr 34 min drive from Westbrook)
Step aboard CrunchTime Sport Fishing, a fully restored 1978 Rose Brothers Custom Charter Headboat, designed for comfort and performance.
trips from
US $750

Frequently Asked Questions about Boat Tours in Westbrook

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Boating in Westbrook

Discover Westbrook boating charters and explore a classic New England shoreline set along the tranquil waters of Long Island Sound. Westbrook is known for easy-going seas, scenic coves, and sheltered inlets that make it a welcoming destination for first-time boaters and seasoned captains alike. Launch into calm waters ideal for leisurely cruises, wildlife spotting, and relaxed days on the water with family and friends.

With a mix of open Sound and winding tidal channels, Westbrook offers variety in every itinerary. Glide past sandy beaches, quiet marshes, and picturesque waterfront homes, or chart a course to nearby islands and coastal landmarks for a memorable half-day or full-day outing. Anglers appreciate accessible nearshore grounds, while photographers and sunset seekers love the golden evening light over the Sound.

Westbrook boating charters range from intimate center consoles and sailboats to comfortable pontoons and spacious cruisers, making it simple to match your group size and style of adventure. Choose a captained charter to sit back and relax, or take the helm on a rental for a self-guided escape. Whether you’re planning a mellow beach hop, a scenic picnic at anchor, or a celebratory cruise, Westbrook delivers calm conditions, charming scenery, and effortless coastal vibes all season long.

What people said about boating in Westbrook

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