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,
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,
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.
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.
Set sail on an unforgettable journey with Artemis Sailing Charters aboard the beautifully restored 1994 Sundeer Pilothouse 64 Sailing vessel, based out of Gloucester.
"Captain Rick and Deb were wonderful hosts aboard the Artemis." — Amy,
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.
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,
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,
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,
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.
