Gloucester Boat Tours

The best out of 29 boat tours in Gloucester - enter dates to check availability

Gloucester Boat Tours

29 boats available

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Top Boat Tours in Gloucester

Gloucester: 29 boats available

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Listing image
Downeast silhouette
35 ft
Up to 6 people
5.0
/5
(1 review)
88 external reviews
Gloucester
Step aboard Tuna Tail Charters for an unforgettable adventure out of Gloucester.

"What an AMAZING day out on the water! From start to finish, this fishing charter exceeded my expectations." —⁠ Heather,
trips from
US $579
Listing image
Downeast silhouette
28 ft
Up to 6 people
4.8
/5
(2 reviews)
365 external reviews
Gloucester
Step aboard Lyla Rose Fishing Charters, a beautifully restored 28’ BHM Downeast vessel, based in the historic fishing hub of Gloucester.

"We went on a 4 hour whale watching trip with captain Matt and it was wonderful." —⁠ Deanna,
+1
trips from
US $500
Listing image
Walkaround silhouette
40 ft
Up to 34 people
Just listed
5+ external reviews
Gloucester
Experience authentic Gloucester from the water aboard Cape Ann Harbor Tours, a classic 1980 North Carolina–built wood hull walkaround vessel, offering a truly local and memorable boating experience.
trips from
US $960
Listing image
Sportfishing silhouette
36 ft
Up to 6 people
Gloucester
Set sail on a 1976 Harris Custom Sportboat, fully restored in 2023, and based out of Gloucester. This sleek, powerful vessel offers a thrilling experience for up to six guests.
trips from
US $600
Listing image
Headboat silhouette
53 ft
Up to 46 people
4.8
/5
(2 external reviews)
Gloucester
Step aboard Cape Ann Cruises—a beautifully restored 1967 Royal Lowell-designed Phil Fessenden Custom Headboat, now modernized in 2023 for comfort, charm, and performance.
+1
trips from
US $1,400
Listing image
Catamaran silhouette
43 ft
Up to 6 people
Gloucester
Step aboard a beautifully restored 1993 Allure Marine Privilege 43 Catamaran (refit 2023), offering a smooth, spacious, and intimate sailing experience for up to 6 guests out of Gloucester.
+1
trips from
US $650
Listing image
Downeast silhouette
31 ft
Up to 6 people
4.7
/5
(2 external reviews)
Beverly (12.5 miles from Gloucester)
Solitude Fishing Charters is a beautifully restored 1982 BHM 31 Downeast vessel (refitted in 2020), offering the perfect blend of classic New England charm and modern comfort.
trips from
US $850
Listing image
Center console silhouette
31 ft
Up to 6 people
5.0
/5
(2 reviews)
28 external reviews
Newburyport (42 min drive from Gloucester)
Set sail with 30 Fathom Charters aboard a beautifully restored 1999 Stamas Tarpon 29 Center Console, docked in scenic Newburyport.

"What a great experience and would highly recommend this experience to anyone." —⁠ John,
trips from
US $300
Listing image
Walkaround silhouette
25 ft
Up to 6 people
4.9
/5
(82 external reviews)
Essex (12 min drive from Gloucester)
Climb aboard Agawam Boat & Fishing Charters, a sleek 2015 Parker 2510 Sportfish Walkaround ready to take you on an unforgettable adventure from Essex! Designed for comfort and performance, this vessel accommodates up to six guests and is powered by a
+3
trips from
US $225
Listing image
Cruiser silhouette
38 ft
Up to 6 people
5.0
/5
(13 reviews)
Boston (48 min drive from Gloucester)
Take a Cruise with Trinacria Cruising Boston for an unforgettable adventure through the scenic waters of Boston Harbor, the Gulf of Maine, and Cape Cod Bay.

" We had an incredible time on our boat excursion with Riccardo and Rachel!" —⁠ Erin,
+2
trips from
US $300

Frequently Asked Questions about Boat Tours in Gloucester

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Boating in Gloucester

Experience the charm of Gloucester, a picturesque coastal town in Massachusetts, with our exceptional Gloucester Boat Tours. Located on historic Cape Ann, Gloucester offers a blend of maritime heritage, stunning natural beauty, and vibrant culture. Whether you're interested in exploring the bustling harbor, witnessing majestic lighthouses, or enjoying the thrill of lobstering, Gloucester has something for everyone.

Choose from a variety of tours that cater to different interests. Take a Lighthouse Cruise to admire six iconic lighthouses, including those at Eastern Point, and enjoy the scenic views of Cape Ann's rugged coastline. Alternatively, join a Harbor Tour to discover the famous fishing fleet, historic landmarks like Stage Fort Park and Norman's Woe, and artistic hotspots like Rocky Neck Art Colony.

For a more leisurely experience, opt for a Sunset Cruise aboard unique boats like the Friki Tiki, offering an "island vibe" amidst Gloucester Harbor's stunning scenery. If you prefer a more traditional sailing experience, board the Schooner Thomas E. Lannon and enjoy a relaxing sail while absorbing the rich maritime history of the area.

No matter which tour you choose, you'll be surrounded by the beauty of Gloucester's shores, rich history, and vibrant community. Let your Gloucester boat tour be an unforgettable adventure amidst New England's most captivating coastal scenery.

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