Westbrook Boat Tours
The best out of 16 boat tours in Westbrook - enter dates to check availability
36 ft
Up to 6 people
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.
trips from
US $540
35 ft
Up to 6 people
5.0
/5
(185 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
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
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
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
25 ft
Up to 6 people
5+ external reviews
Southold (1 hr 58 min drive from Westbrook)
Set sail with North Fork Adventures Charters, a 2001 Parker 2510 Pilothouse offering unforgettable boating experiences from Southold! With room for up to six guests, this sturdy and well-equipped vessel is powered by twin 150 HP Yamaha outboard engines, c
trips from
US $500
30 ft
Up to 6 people
5.0
/5
(18 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
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
28 ft
Up to 6 people
5.0
/5
(33 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
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