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Popular Sailing, Catamaran & Gulet Tours Charters in Massachusetts  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sailing, Catamaran & Gulet Tours in Massachusetts, MA- BoatBooker

Massachusetts

Massachusetts, United States

Discover why Massachusetts Boating Charters are a favorite for coastal getaways. With a rugged Atlantic shoreline, picturesque islands, and storybook harbors, Massachusetts delivers a blend of scenic cruising, wildlife encounters, and classic New England maritime charm. From calm, family-friendly bays to invigorating open-water passages, you’ll find waterways suited to sailing, powerboating, and everything in between.Set a course along Boston Harbor for skyline views and historic waterfronts, then trace the North Shore for rocky headlands and iconic lighthouses. South of the city, protected inlets and sandy beaches lead you toward Cape Cod, where broad horizons, tidal flats, and postcard towns invite easy day trips and longer adventures. The Cape’s waterways connect you to island escapes, with harbors known for quaint villages, beachy anchorages, and lively summer scenes.Nature lovers can time outings for peak marine life seasons, scan for seabirds along the shoals, or plot a relaxed hop between coves at golden hour. Anglers, sunset cruisers, and sightseers alike appreciate the variety—harbor tours, island shuttles, sailing excursions, and customizable itineraries that match your pace and interests.Whether you’re charting a weekend with friends or introducing family to life on the water, Massachusetts offers reliable winds, well-serviced marinas, and welcoming harbor towns. Book a vessel that fits your crew, pick a launch point, and experience a classic New England coastline designed for memorable days under way.

Experience the breathtaking beauty of Massachusetts from a unique perspective with Massachusetts Boat Tours. This stunning coastal state offers an array of exciting boating experiences that cater to all tastes. From the historic waters of Boston Harbor, where you can explore iconic landmarks like the USS Constitution and the Boston Tea Party Ships, to the majestic vistas of Cape Cod, there’s no shortage of adventure.

Enjoy a Boston Duck Boat Tour that seamlessly combines land and water exploration, offering a fun and educational journey. For nature lovers, the Boston Whale Watching Cruise is a must, taking you to the renowned Stellwagen Bank National Marine Sanctuary to see humpback whales and more. Alternatively, unwind on a Sunset Cruise around Boston Harbor, offering spectacular views of the city skyline.

Outside of Boston, destinations like Salem offer captivating harbor tours, allowing you to immerse yourself in the rich maritime history of the region. Whether you’re interested in sailing, cruising, or simply enjoying the scenic beauty of Massachusetts, there’s a boat tour designed just for you. So, set sail and discover why Massachusetts boat tours are a must-do experience for anyone visiting this incredible state.

Enjoy a 3-hour sailing adventure aboard Tandemeer, our 60-foot luxury Ketch, exploring Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound. Feel the wind in your hair, take in stunning views, and dive in for a swim whenever you like.

Charters can start at any time between 10 AM and 4 PM—just give us a call to schedule your preferred departure.

United States

Island Sailing Tours

Martha's Vineyard

Set sail on the beautifully restored 1980 Nautical Development 56 Sailing yacht, refreshed in 2024, and based out of picturesque Martha&#039;s Vineyard. Accommodating up to six guests, this classic sailing vessel combines timeless charm with modern comfor

This is a four-hour sail around the bay. This will allow ample time for a mix of sailing, swimming, exploring, and byob/food dining. We can cater to your desires and make a custom itinerary that 

works for you and your guests.

Martha’s Vineyard Charter Company

Set sail around the scenic waters of Martha&rsquo;s Vineyard aboard Our Passion, a beautifully maintained 1983 Pearson 422 Sailing Yacht operated by Martha&rsquo;s Vineyard Charter Company. Departing from charming Vineyard Haven, this classic sailing vess

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

Gloucester

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

Enjoy the world-class sailing grounds of Buzzards Bay and the picturesque coastlines of Dartmouth, New Bedford, and Fairhaven, Massachusetts. Whether you want to hoist the sails and take a turn at the wheel, or simply sit back, relax, and enjoy the harmony of sail and sea, an excursion on Omoo will be the highlight of your day.

Buzzards Bay Yacht Charters – Pearson 35

New Bedford

Buzzards Bay Yacht Charters offers unforgettable private day sails aboard a beautifully maintained 1979 Pearson 35 sailboat, based in New Bedford, MA. Perfect for couples, families, or small groups, this classic sailing yacht accommodates up to 6 guests, 

We depart from Falmouth Harbor and, depending on wind and tide, sail toward Nobska Lighthouse, Martha’s Vineyard, or Falmouth Heights, offering a unique experience every time on the water. Enjoy spacious decks with comfortable seating for up to 49 passengers, music onboard, and a full bar available throughout the trip (no BYOB allowed). Children are welcome, and for private charters you may bring light snacks or catering.

Schooner Liberté

Falmouth

Schooner Libert&eacute; is a beautifully maintained 2002 sailing vessel (Deadly Dix 77) based in Falmouth, offering an unforgettable on-the-water experience for up to 49 guests. Powered by a 130 HP diesel inboard engine with a cruising speed of up to 8 kn

Sailing, Catamaran & Gulet Tours in Massachusetts

Top Sailing, Catamaran & Gulet Tours in Massachusetts