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Popular Boat & Yacht Tours Charters in Gloucester  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Boat & Yacht Tours in Gloucester, MA- BoatBooker

Gloucester

Gloucester, United States

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.

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.

This trip is for clients wishing to scatter a loved one’s ashes at sea. Guests can join the ceremony, or the captain and crew can perform and document it without guests. Trinacria will travel 3 miles offshore (per EPA regulations). The crew will conduct a custom-tailored ceremony, and clients will receive photos and a Certificate of Service, including the deceased's name, date, and coordinates, signed by the captain and suitable for framing. The start time is flexible and can often be adjusted.

United States

Trinacria Cruising Boston

Boston

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. Aboard the luxurious 38&rsquo; Stamas yacht, you&#039;ll be guided by Captain Riccardo, a seasoned

Embark on a breathtaking 3-hour sightseeing cruise from Cripple Cove Landing in historic Gloucester! Glide through scenic waters, taking in stunning coastal views, lighthouses, and abundant marine life. Spot playful seals, seabirds, and maybe even a majestic whale! Relax, unwind, and enjoy the calming sounds of the ocean. Beer and wine are welcome, but hard liquor is not. Breathe in the salty air, capture unforgettable memories, and book your unforgettable voyage today!

Tuna Tail Charters

Step aboard Tuna Tail Charters for an unforgettable adventure out of Gloucester. This beautiful 2008 Duffy 35 Downeast cruiser comfortably accommodates up to six guests, making it perfect for intimate whale watching trips, scenic eco tours, or relaxing bo

On this trip, you will set out to enjoy one of Gloucester’s many beautiful beaches. Wingearsheek Beach in the Annisquam River is an excellent destination for families, and friends to enjoy some fun in the sun. Your boat will anchor up just off of the beach, where your captain will shuttle you in aboard the zodiac inflatable tender. Optional beach toys, beach chairs, a cooler, a children’s kayak, and a 20’ lily pad floating mat can be provided at no additional cost. Flexible departure time if necessary.

Lyla Rose Charters

Step aboard Lyla Rose Fishing Charters, a beautifully restored 28&rsquo; BHM Downeast vessel, based in the historic fishing hub of Gloucester. With a 2022 restoration, this 1987 classic blends vintage charm with modern amenities, providing an unforgettabl

We cruise along the Annisquam River from Gloucester Harbor to Ipswich Bay and back, offering a beautiful and enjoyable experience. It’s a fun-filled trip with stunning scenery!

10 Point Charters

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. Powered by twin 400 HP Caterpillar diesel inboard engines, it boasts a cruisin

Enjoy an unforgettable experience aboard the WeJack with Cape Ann Cruises, perfect for groups from 2 to 46. Cruise America’s oldest seaport in Gloucester, MA, is just steps from the train station and offers easy access to Boston. From fishing trips to milestone birthdays, weddings, reunions, music cruises, private whale watching, and celebrations of life, we offer it all. See castles, mansions, lighthouses, fishing vessels, and stunning nature. A unique way to gather, celebrate, and enjoy the ocean!

Cape Ann Cruises

Step aboard Cape Ann Cruises&mdash;a beautifully restored 1967 Royal Lowell-designed Phil Fessenden Custom Headboat, now modernized in 2023 for comfort, charm, and performance. Departing from Gloucester, this spacious vessel welcomes up to 46 guests, maki

Sunset cruise on the beautiful Merrimack River. Relax in comfort as we cruise the Newburyport waterfront and explore upriver to Amesbury and West Newbury. Times can be customized if needed

30 Fathom Charters

Newburyport

Set sail with 30 Fathom Charters aboard a beautifully restored Stamas Tarpon 29 Center Console, docked in scenic Newburyport. Fully refurbished in 2023, this vessel blends classic reliability with modern comfort, powered by twin 300 HP Suzuki outboards fo

Departure times are flexible between 8 AM - 6 PM.
Cruise down the Essex River, travel through the Great Salt Marsh estuary, where you will likely encounter wildlife up close on your private cruise for up to 6 passengers.  Pass scenic Cross Island, Conomo Point, Hog Island, and see the gulls over Crane Beach in Ipswich. You may encounter clammers, colorful kayaks, or sailboats in the Essex River or bay. Bring your own food, appetizers, beer, wine, or soft drinks.  Captain Ted will provide coolers and ice.

Agawam Boat & Fishing Charters

Essex

Climb aboard Agawam Boat &amp; 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 

Tour the beautiful harbors of Marblehead, Salem, Manchester, and Beverly. Then head out for some sightseeing around the picturesque islands all around the north shore!

Keepin It Reel Charters

Marblehead

Step aboard Keepin It Reel Charters for an unforgettable day on the water. This sleek 2015 Sea Hunt Gamefish 25 Center Console, based out of scenic Marblehead, is the perfect choice for up to six guests looking to explore in comfort and style. Powered by 

Spend 8 unforgettable hours whale watching offshore in Massachusetts—experience the beauty of the open ocean and encounter majestic whales in their natural habitat.

Solitude Fishing Charters

Beverly

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. Based in Beverly, MA, she comfortably accommodates up to 6 guests, ideal for pr

Our private charters in Gloucester are fully customizable to your specific requests or expertly arranged by Captain Gregory. Enjoy scenic sightseeing, unwind on the water, and experience the very best of the Massachusetts coast at your own pace.

Cape Ann Harbor Tours – King Eider

Experience authentic Gloucester from the water aboard Cape Ann Harbor Tours, a classic 1980 North Carolina&ndash;built wood hull walkaround vessel, offering a truly local and memorable boating experience. Departing from Gloucester, this spacious boat acco

Boat & Yacht Tours in Gloucester

Top Boat & Yacht Tours in Gloucester