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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

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.

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!

United States

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

Experience the beauty and history of Boston with a captivating harbor boat cruise! 
Glide across the sparkling waters and enjoy stunning views of the skyline, including landmarks like the USS Constitution and the Charlestown Navy Yard. Knowledgeable guides will share fascinating stories of the city’s maritime heritage, from the Boston Tea Party to the American Revolution.

With comfortable seating and fresh sea breezes, this cruise is perfect for couples, families, and history buffs alike. 

Jimmy Rig Charters

Boston

Set sail on a memorable adventure with Jimmy Rig Charters aboard the sleek and powerful 2021 Cobia 262 CC Center Console, docked in vibrant Boston. Perfect for up to 4 guests, this boat is designed for comfort, speed, and versatility. Powered by two 200 H

Set sail on a 4-hour Atlantic boat trip from Hampton, where the beauty of the coastline meets the vast ocean. Enjoy breathtaking views, explore hidden coves, and relax with a cool ocean breeze. With flexible departure times, you can tailor the trip to fit your schedule. Whether soaking in the sun or taking in the serene surroundings, this is an experience you'll treasure forever.

Reel Balance Fishing Charters

Hampton

Set sail on an unforgettable adventure with Reel Balance Charters, a premium 2021 Blackfin 252CC Center Console, based out of Hampton. Designed for up to six guests, this exceptional vessel combines comfort, speed, and power for a memorable day on the wat

We do it all—and some activities just take a little more time than others. With years of experience (longer than it takes whale bones to decompose!), we’ll tailor your trip exactly to what you want to do. Trips are a la carte at $180/hr—contact us to plan your adventure!

Central NH Guides

Experience the ultimate boating adventure with Central NH Guides, a 2017 Duffy Downeast based in Hampton. Perfect for up to six guests, this powerful vessel is equipped with a 650 HP diesel inboard Mack engine, reaching speeds up to 35 knots, ensuring bot

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.

30 Fathom Charters

Newburyport

Set sail with 30 Fathom Charters aboard a beautifully restored 1999 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 outboar

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 

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