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Gloucester Boat Tours

The best out of 30 boat tours in Gloucester - enter dates to check availability

Gloucester Boat Tours

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Top Boat Tours in Gloucester

Gloucester: 30 boats available

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Listing image
28 ft
Up to 6 people
Lyla Rose Charters
4.8
/5
(2 reviews)
411 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
35 ft
Up to 6 people
Tuna Tail Charters
5.0
/5
(1 review)
105 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
40 ft
Up to 34 people
Cape Ann Harbor Tours – King Eider
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
36 ft
Up to 6 people
10 Point Charters
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
53 ft
Up to 46 people
Cape Ann Cruises
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
64 ft
Up to 6 people
Artemis Sailing Charters
5.0
/5
(1 review)
Gloucester
Set sail on an unforgettable journey with Artemis Sailing Charters aboard the beautifully restored 1994 Sundeer Pilothouse 64 Sailing vessel, based out of Gloucester.

"The family and I had an amazing time on Artemis sailing with Captain Rick and his wife Deb." —⁠ Patrixk,
+2
trips from
US $450
Listing image
36 ft
Up to 6 people
Private Catamaran Sailing Adventure
5.0
/5
(1 review)
Gloucester
Step aboard a beautifully 2010 Mahe 36 Evolution Catamaran , offering a smooth, spacious, and intimate sailing experience for up to 6 guests out of Gloucester.

"THANK you, Captain Lu and his first mate! The boat was awesome too." —⁠ Elinor,
+1
trips from
US $650
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38 ft
Up to 6 people
Trinacria Cruising Boston
5.0
/5
(28 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 thought we knew Boston, but seeing it from the water with Captain Riccardo and Rachel was an entirely different experience!" —⁠ Victoria,
+10
trips from
US $300
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31 ft
Up to 6 people
Solitude Fishing Charters
4.8
/5
(7 external reviews)
Beverly (25 min drive 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
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31 ft
Up to 6 people
30 Fathom Charters - Private Boat Cruises
5.0
/5
(9 reviews)
Newburyport (42 min drive from Gloucester)
Experience the beauty of the New England coast aboard 30 Fathom Charters, a beautifully restored Stamas Tarpon 29 Center Console departing from historic Newburyport, Massachusetts.

"I booked a last minute afternoon cruise with Kristian and Anna, and it was the best thing I’ve done all summer!" —⁠ Sabrina,
trips from
US $300

Frequently Asked Questions about Boat Tours in Gloucester

According to customer reviews, some of the most popular boat tours in Gloucester, Massachusetts are:
Full list of top boat tours in Gloucester
According to customer reviews, some of the most popular boat tours in Gloucester, Massachusetts are:
Full list of top boat tours in Gloucester
The average Gloucester boat trip price for a 4 hour private trip is US $831 based on prices on BoatBooker.com.
The average Gloucester boat trip price for a 4 hour private trip is US $831 based on prices on BoatBooker.com.
The top 5 most popular boat types you can rent in Gloucester, by number of boats available are:
The top 5 most popular boat types you can rent in Gloucester, by number of boats available are:
The top 5 most popular boat categories you can rent in Gloucester, by number of boats available are:
The top 5 most popular boat categories you can rent in Gloucester, by number of boats available are:
According to customer reviews on BoatBooker.com, some of the best rated boat tours in Gloucester are:
According to customer reviews on BoatBooker.com, some of the best rated boat tours in Gloucester are:
The average price of boat tours in Gloucester is:
  • 1-hour boating trips – US $705
  • 2-hour boating trips – US $1,239
  • 3-hour boating trips – US $1,216
  • 4-hour boating trips – US $1,900
  • 5-hour boating trips – US $1,250
  • 6-hour boating trips – US $2,825
  • 8-hour boating trips – US $3,175
  • 10-hour boating trips – US $6,400
  • 12-hour boating trips – US $7,500
  • 18-hour boating trips – US $1,958
The average price of boat tours in Gloucester is:
  • 1-hour boating trips – US $705
  • 2-hour boating trips – US $1,239
  • 3-hour boating trips – US $1,216
  • 4-hour boating trips – US $1,900
  • 5-hour boating trips – US $1,250
  • 6-hour boating trips – US $2,825
  • 8-hour boating trips – US $3,175
  • 10-hour boating trips – US $6,400
  • 12-hour boating trips – US $7,500
  • 18-hour boating trips – US $1,958
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Boating in Gloucester

Discover Gloucester, Massachusetts, United States—an authentic New England harbor where working waterfronts meet dramatic Atlantic scenery. Known for its proud maritime heritage and easy access to Cape Ann's rugged coastline, Gloucester boating charters connect you with rocky headlands, pristine beaches, and wildlife-rich waters ideal for sightseeing and adventure.

Launch from Gloucester Harbor to explore sheltered coves, classic lighthouses, and island-dotted passages perfect for leisurely cruising or photography. In season, charters often venture toward productive offshore grounds for memorable wildlife spotting, while inshore routes reveal calm bays suited to family-friendly outings and relaxed sunset trips.

Anglers will find varied opportunities around reefs and rips, while sailing enthusiasts enjoy steady coastal breezes and panoramic views of historic shorelines. Kayak- and paddle-friendly inlets offer a slower pace, and flexible itineraries make it easy to combine harbor touring with beach landings or lighthouse viewing.

With convenient marina facilities, knowledgeable local captains, and options ranging from private powerboats to classic sailboats, Gloucester boating charters make it simple to tailor your time on the water. Whether you're planning a half-day harbor cruise or a full-day coastal exploration, this Cape Ann destination delivers quintessential New England character, sea air, and unforgettable horizons.

What people said about boating in Gloucester

  • 5.0
    /5
    (4 hour sailing trip for Pat B)

    Amazing Experience!!!

    If this is your first time boating you’re in for a treat. It’s an amazing experience to view the legendary harbor at the oldest working harbor in the US. You owe it to yourself to get out there and see what Gloucester and Cape Ann have to offer!
    Patrixk B.
    Patrixk B.
    Reviewed on September 1, 2025

How people rated boat trips in Gloucester

  • Artemis Sailing Charters
    Artemis Sailing Charters
    Boat rentals in Gloucester
    5.0
    /5
    (4 hour sailing trip for Pat B)

    Amazing Experience!!!

    The family and I had an amazing time on Artemis sailing with Captain Rick and his wife Deb. What an amazing experience to sail on such a beautiful yacht and with such wonderful people. If you've never sailed or are an experienced sailor, you will truly enjoy this great experience and discover Gloucester and the surrounding area. This sailing yacht is super stable, fast and fun. Make new friends, new experiences and amazing memories to last a lifetime! Sail Artemis!
    Patrixk B.
    Patrixk B.
    Reviewed on Sep 1, 2025
  • Lyla Rose Charters
    Lyla Rose Charters
    Boat rentals in Gloucester
    5.0
    /5
    (5 Hour Trip – Whale Watching (AM))

    Wonderful experience!

    We went on a 4 hour whale watching trip with captain Matt and it was wonderful. The whales were hiding from us that day but captain Matt made sure we had a great time nonetheless! We had 3 kids with us and we stoped several time to catch fish, saw dozens of sea lions and fed them! The boat was very comfortable with seating out side and inside out of the wind and sun. 10/10 would recommend and do again. Thank you captain Matt
    Deanna S.
    Deanna S.
    Reviewed on Jun 11, 2025