Your Itinerary

1 Boston, MA
Welcome aboard the American Constitution!

2Portland, ME
Maine's most historic seaport overlooks beautiful Casco Bay. Spend your visit exploring its gallant 360-year history or check out its amazing cultural scene. Big-city excitement blends delightfully with small-town charm here as fishing vessels bustle in the harbor and Victorian-era buildings still line cobblestone streets.

3Rockland, ME
Full of classic schooners, this charming village is considered the "Tall Ship Capital of Maine." Enjoy the summer sun and refreshing sea breezes as you watch beautiful ships sail into the harbor or browse the quaint shops and art galleries.

4Bar Harbor, ME
The natural beauty that surrounds Bar Harbor is accented with ocean cliffs, glacier‐formed lakes and valleys, stunning mountain vistas, and pine forest. This beauty has been captured in the works of Thomas Cole, Frederic Edwin Church, and many other great artists. Lobstering is a centuries‐old industry that continues to thrive in Bar Harbor as well as boat building, another traditional business that is an important part of the economy. Though Bar Harbor region is best known for its outdoor activities, it is also home to small museums, cultural attractions, and historically significant landmarks.

5Boothbay Harbor, ME
This lovely, historic town is lined with shops, boutiques, and picture-perfect harbors dotted with lobster boats, pleasure crafts, and windjammers. Boothbay is the largest boating harbor north of Boston, earning the moniker of "Boating Capital of New England."

6Bath, ME
Long known as the "City of Ships," Bath finds its identity in shipbuilding. From its architecture and cultural offerings to its urban downtown, Bath's shipbuilding roots define its character. Walk Bath's streets and admire the seaport's tree-lined avenues, graced with classic examples of American architecture. Or explore the nationally acclaimed Maine Maritime Museum, which offers a variety of exhibits about Maine's nautical history.

7Gloucester, MA
Located a few miles from Boston, Gloucester is the home to America's original seaport and the oldest working art colony in North America. The town’s picturesque waterfront has drawn fishermen, artists, and visitors for over four hundred years. With over 60 miles of coastline, there is a wealth of stunning views to enjoy and plenty of fresh seafood to savor.

8Day of Cruising
As you cruise from Gloucester to Newport, indulge yourself in the awe-inspiring New England landscapes that stretch out before you. Treat yourself to a day of pure relaxation on your private balcony or on the sun deck. Or, enjoy an engaging presentation by our onboard expert.

9Newport, RI
Nestled within Narragansett Bay is Newport, the yachting capital of the world. As you stroll along the beautiful beaches, historic neighborhoods, bustling wharves, and scenic waterfront, you will find Newport offers something for everyone. Visit the Herreshoff Marine Museum and America's Cup Hall of Fame. Explore Newport's fabled past with glimpses of opulent seaside estates along the "Avenue of the Mansions."

10Martha's Vineyard, MA
During the 18th and 19th centuries, Martha's Vineyard was a hub for merchant ships carrying exotic cargo from the far corners of the world. Today, the island is one of the most popular vacation spots in New England, comprised of six distinct towns. Historic Edgartown is the most genteel town on the island, featuring freshly painted white clapboard colonial homes and manicured gardens.

11Boston, MA
Welcome back to the historic city of Boston, best known for its famous baked beans, Fenway Park, The Boston Marathon, and the bar from the '80s sitcom Cheers. Let us help you to plan your journey home, or stay to explore this vibrant city further.