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

Sunset & Dinner Cruises 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 have a loved one’s ashes Scattered at sea. This is an Unattended trip, the Captain will perform the trip without guests onboard. The Captain will travel 3 miles offshore (per EPA regulations) & conduct a custom-tailored ceremony. Client will be provided photos & a Framed, Captain Endorsed Certificate of Service, documented with the deceased's name, the date of service, & coordinates of service. Ashes can be Mailed or Hand Delivered to the Captain in advance.

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

Enjoy a relaxing cruise through the scenic Annisquam River as you head out into Ipswich Bay for an absolutley breathtaking view of the sunset out on the water!

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

Departing from Fan Pier in Boston's Seaport, we'll embark on a scenic journey around the harbor and outer islands. Along the way, we'll pass three historic lighthouses, and I’ll share insights into the rich history of the islands and their landmarks. For those looking to step ashore, several islands offer docking opportunities to explore their natural beauty up close.

Boston Fish Charters

Boston Fish Charters invites you on an unforgettable adventure in Boston Harbor! Our 1988 Wellcraft V20 Steplift Cuddy Cabin, beautifully restored in 2023, offers an intimate and thrilling experience for up to three guests&mdash;but come mid-June 2025, ou

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

Hampton

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

Set sail from Scituate, MA, on a 3-hour adventure tailored to your schedule. Whether you’re looking for a relaxing boat tour, a vibrant booze cruise, a stunning sunset tour, or a fun-filled sandbar trip, we’ll make it an unforgettable experience. Hop aboard and let the beauty of the coast guide your day on the water!
Please note that the tour depends on my calendar availability.

After Hours Boat Tours

Scituate

After Hours Boat Tours offers unforgettable experiences aboard a Boston Whaler Conquest 255 Walkaround, departing from Scituate. Accommodating up to six guests, trips are fully flexible&mdash;choose your preferred time (subject to availability) and enjoy 

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 

Set out on a two‑hour sailing escape that reveals Gloucester Harbor from a fresh, adventurous perspective. Aboard our spacious, stable catamaran, you’ll explore the working waterfront, historic lighthouses, and the rugged edges of Cape Ann, all at an easy, unhurried pace with Capt. Lu at the helm, you’ll experience a calm, knowledgeable guide who brings local insight and a warm personal touch to every trip.

Private Catamaran Sailing Adventure

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. This private charter blends classic sailing charm with modern comfort, making it ideal for rela

Experience the magic of Boston from the water with our Harbor Glow Tour, a relaxing 2-hour sunset experience for up to 6 passengers. Sail past the stunning Boston skyline and the Harbor Islands as the city begins to glow at dusk. Bring your own snacks and drinks and enjoy the perfect outing for couples, families, or small groups looking to unwind and take in unforgettable views.

Boston Slainte Charters

Boston Slainte Charters is a 2005 Albin Tournament Cuddy based in Chelsea, offering an intimate and comfortable boating experience for up to 6 guests. Powered by a reliable 300 HP Yanmar diesel inboard engine, the vessel cruises smoothly at up to 30 knots

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

Sunset & Dinner Cruises in Gloucester

Top Sunset & Dinner Cruises in Gloucester