8 Picture-Perfect New England Cruise Ports You Don’t Want to Miss

Welcome to Part 2:  My favorite New England cruise ports.

While many of these cruise ports are included on a typical Canada / New England cruise, some cruise ships only visit these places on itineraries that are exclusively to New England.  All of these cruise ports will delight even the most jaded of cruisers.  From natural beauty and outdoorsy active excursions to great local food and quaint cafés, a voyage that includes any of these New England cruise ports, will be spectacular.

Here then are four more of my favorite New England cruise ports.  Use the link at the bottom to read about the first four cruise ports.

Photo credit: Eastport-me.gov – Don Dunbar Photography

Eastport, Maine

If you want to visit the easternmost city in the continental U.S., consider a cruise to Eastport.  It’s a destination entirely comprised of islands.

Eastport’s cruise port is located on Moose Island, the largest island in the archipelago.  Cruise ships dock in the heart of downtown, within walking distance to the town’s main street.

From there, explore the beautifully preserved 19th-century Italianate architecture, which is on the National Register of Historic Places.  Another must-see is to tour Roosevelt Campobello International Park and visit Franklin Delano Roosevelt’s beloved summer cottage.

Finally, for a memorable souvenir, pick up a jar of Raye’s mustard from the only remaining traditional stoneground mustard mill in North America.

Photo: Wiki-Commons

Gloucester, Massachusetts

Located just north of Boston, on the Cape Ann promontory, Gloucester is the oldest working seaport in America.  Enjoy a leisurely stroll along the 1.2 mile Harbor Walk before making your way downtown to embark on a self-guided historic and cultural tour of Gloucester.

Artists have been drawn to this iconic seaside town for decades, and the result is a thriving modern-day community.  The Rocky Neck Art Colony is the go-to place for handcrafted souvenirs, paintings and ceramics.

If there’s enough time, step aboard The Lannon, a 65-foot schooner, for a two-hour harbor cruise.  Cruise lines to Gloucester include American Cruise Lines, offering sailings to Gloucester on its New England itineraries.

Photo credit: Wiki-Commons; Hannahjones

Rockland, Maine

Nestled in Penobscot Bay, Rockland is nicknamed the Jewel of the Maine Coast.  And it’s about as charming a New England town as you can find.  Cruise lines such as Norwegian and American Cruise Lines offer itineraries to Rockland.

Historic landmarks abound, including nine schooners of the Maine Windjammer fleet, over a dozen lighthouses and the beautifully preserved Rockland Main Street.  Rockland’s most popular indoor attraction is the Farnsworth Art Museum and the Wyeth Center art collection.  These buildings house three generations of Wyeth artwork.  If you’re a car buff, visit nearby Owls Head Transportation Museum to check out the first aircraft and automobiles from the late 19th and early 20th centuries.

Marthas Vineyard on a New England cruise.
Photo credit: Martha’s Vineyard Chamber of Commerce/Mark Lovewell

Martha’s Vineyard, Massachusetts

Located seven miles off the coast of Cape Cod, Martha’s Vineyard is known for its stately lighthouses, gingerbread cottages and charming towns.  You’ll want to explore historic Edgartown before making your way to Oak Bluffs to admire Victorian cottages and take a spin on Flying Horses Carousel.  It’s the oldest continuously operating carousel in the country.

If you arrive hungry, rest assured.  The island offers everything from home-made honey-covered donuts to freshly steamed lobster and old-time ice cream parlors.

Of course, you won’t want to miss grabbing a bite at the legendary Black Dog Tavern in Vineyard Haven.

Read next: My other four favorite New England cruise ports.

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