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The top boating charters in Gloucester

Gloucester

Activities

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Boat Types

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Step aboard Lyla Rose Fishing Charters, a beautifully restored 28’ BHM Downeast vessel, based in the historic fishing hub of Gloucester. 

Lyla Rose Charters

Step aboard Tuna Tail Charters for an unforgettable adventure out of Gloucester. 

Tuna Tail Charters

Set sail on a 1976 Harris Custom Sportboat, fully restored in 2023, and based out of Gloucester. 

10 Point Charters

Set sail on an unforgettable journey with Artemis Sailing Charters aboard the beautifully restored 1994 Sundeer Pilothouse 64 Sailing vessel, based out of Gloucester. 

Artemis Sailing Charters

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. 

Cape Ann Cruises

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. 

Trinacria Cruising Boston

Climb aboard Agawam Boat & Fishing Charters, a sleek 2015 Parker 2510 Sportfish Walkaround ready to take you on an unforgettable adventure from Essex! 

Agawam Boat & Fishing Charters

Set sail with 30 Fathom Charters aboard a beautifully restored 1999 Stamas Tarpon 29 Center Console, docked in scenic Newburyport. 

30 Fathom Charters

Step aboard Keepin It Reel Charters for an unforgettable day on the water. 

Keepin It Reel Charters

Set sail on an unforgettable adventure with Reel Balance Charters, a premium 2021 Blackfin 252CC Center Console, based out of Hampton. 

Gloucester: 18 boats available

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Gloucester: 18 boats available