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Popular Island Hopping Charters in Massachusetts  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Island Hopping 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.

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

All the same beautiful scenery of our 2 hour Harbor and Seal tours with the added benefit of being able to go a little further!

Circumnavigating around the breathtaking, 8-mile-long,7900 acres of scenic Monomoy Island is a bucket list trip for sightseers, lighthouse enthusiasts, and bird watchers as well. Bring the camera and binoculars because Monomoy never disappoints!

Along with sightseeing, we can do secluded sand bar drop-offs, offshore whale watching, and Pleasant Bay tours.

Got Stryper’s Chatham Eco Tours

Chatham

Did you know that the world-famous &ldquo;Elbow of Cape Cod&rdquo; has three lighthouses, over 60 miles of shoreline, acres of pristine sand bars to explore or relax on, and is home to the largest grey seal colony in New England? Did you also know that Ch

Spend a few hours touring Chatham’s stunning sights. Stage Harbor Lighthouse, the Chatham Fish Pier, Coast Guard Light, Morris Island, Oyster River, Oyster Pond, Monomoy’s north end and clam flats, Tern Island, and the world-renowned Chatham Outer Bars are all within a short boat ride. Along the way, enjoy breathtaking scenery and incredible wildlife. Chatham’s inner waterways are alive with birds, fish, and seals, making this an unforgettable Cape Cod experience.

Got Stryper’s Chatham Adventure Tours

Did you know that Chatham, located on Cape Cod&rsquo;s famous &ldquo;Elbow,&rdquo; is home to three iconic lighthouses, over 60 miles of breathtaking shoreline, and expansive sandbars perfect for exploring or relaxing? It&rsquo;s also home to New England&

The 4 hour trip leaves out of the Bass River and you choose your adventure.  We can cruise the Bass River and anchor for you to swim and enjoy fun in the sun, or head down the coast to Monomoy Island for seal and bird watching, or head up to Lewis Bay and Hyannis inner harbor to see the sights. 
 This trip is customizable and Captain Jim will work with you laying out your options for your 4 hour trip to maximize your experience.   You point we drive!

Bass River Cruise, Harbor & Island Cruises

Dennis

Step aboard the Krista Mari, a 26&prime; Steigercraft Miami with Captain Jim, for a private 2-hour cruise along Bass River. (We also offer extended 4, 6, and 8 hour cruises) Departing from Bass River Marina, this exclusive experience is perfect for up to 

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

Watch the sky ignite aboard ON THE EDGE! Slip out of historic Fairhaven harbor, cruising past iconic lighthouses as the sun melts into Buzzards Bay in a blaze of pink and gold. BYOB, premium sound system & ice-cold storage ready. Perfect for couples, families, or friends (up to 6). 2hr private sunset cruise with Captain Rick. Add charcuterie & drinks for pure magic. Book now – the best sunsets are ON THE EDGE, not from shore! Departure times change with sunset times!

ON THE EDGE

Fairhaven

ON THE EDGE &ndash; Your Ultimate Luxury Family Adventure Machine, Fully-Restored Grady-White Gulfstream 232 Walkaround. Step aboard the stunning ON THE EDGE, a pristine Grady-White 232 Gulfstream that blends classic New England lines with cutting-edge pe

Do what you want, we’ll work with you to create exactly the experience you’re looking for.

Take a private cruise through Boston Harbor and its islands, with stunning skyline and landmark views. Relax and enjoy the city from the water.
Customize your cruise and bring your own snacks and drinks, or upgrade to our stocked cooler package. Choose from 2, 4, or 6-hour options. Book 4 or 6 hours for island excursions, swimming, or lighthouse tours.

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

Cruise over to Martha’s Vineyard and have lunch in either Oak Bluffs or Edgartown Harbor while your captain waits with the boat.

In The Net Sportfishing

Barnstable

Step aboard In The Net Sportfishing, a 2021 Grady-White Fisherman 257 center console designed for speed, comfort, and serious on-the-water adventure out of Barnstable. Powered by twin 200 HP Yamaha outboards, this high-performance vessel reaches up to 45 

Cruise through the scenic waters of Waquoit Bay and experience one of Cape Cod's most beautiful and ecologically significant coastal environments. This relaxing boat tour showcases expansive salt marshes, barrier beaches, pristine shoreline habitats, and abundant wildlife, offering a unique perspective on the region's natural beauty and maritime heritage. 
Perfect for families, couples, nature enthusiasts, and anyone looking to experience Cape Cod from the water. We can pick up from private area docks.

Waquoit Bay & Washburn Island Boat Cruises

Mashpee

Discover the natural beauty and rich coastal heritage of Waquoit Bay on one of our relaxing boat tours and sunset cruises in Mashpee, Massachusetts. Explore the calm waters of this protected estuary as you cruise past salt marshes, barrier beaches, and sc

Beach and boat day with family and friends! Spend the day cruising around in the boat and anchoring at a beach or island. Who doesn’t like jumping off a boat and enjoying a few drinks on a sandbar!

Fishy Business Sportfishing

Plymouth

Summers on Cape Cod and in Plymouth, MA, are made for unforgettable days on the water with family and friends. Join Fishy Business Sportfishing for a fully customizable private boating experience designed around your ideal day at sea. Our 1997 Contender C

Island Hopping in Massachusetts

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Island Hopping

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