Taking a Cruise in New England on a Small Ship

By taking a New England cruise on a small ship, instead of  a large vessel, your access to New England just got greater. You and only a few hundred passengers will sail through inland rivers and tighter coastlines with ease, and still experience top ports in Maine (Bar Harbor and Portland), Rhode Island (Newport) and Massachusetts (Boston). Timing for these itineraries might feature a shorter window than the Caribbean. You’ll be treated to fall foliage or the glory of a New England summer (hello, lobster!) at its prime.

The following are some of the best small ship New England cruises and tips on when to go:

1. Windstar Cruises

Spanning both New England and eastern Canada, Windstar Cruises’ itineraries in late September and early October easily whisk you from Montreal to Boston on the 10-night “Southeast Canada Explorations” sail on board Star Pride. Fan of “Anne of Green Gables?” ShoreTrips’ Island Drive and Anne of Green Gables tour in Charlottetown, Prince Edward Island, Canada, takes you to the famed Green Gables homestead. Windstar’s 12-night “Maritimes & Manhattan” Montreal-bound cruise (also on Star Pride) out of New York City (September and October) steeps you in local royalty via Newport, Rhode Island’s mansions but also affords opportunities to spot Beluga whales off the Gaspé Peninsula—while also folding in a trip to Charlottetown.

2. Maine Windjammer Association

For the sailing enthusiast with dreams of circumnavigating the globe, this Maine-based association operates the largest traditional-schooner fleet in North America (eight total). No more than 20 to 40 guests sail for between three and four nights. It’s no problem if you want to take the wheel (under guidance, of course) or help raise and lower sails. Seeking some Zen? There are two three “yoga, health & wellness” cruises, in August and September, as well as dedicated stargazing, photography/art/film, mixology and music cruises. Five cruises sale this summer and fall to Acadia National Park. Get away from the crowds with ShoreTrips’ The Quiet Side of Acadia tour. Lobsters are included in two ShoreTrips’ tours—Mount Desert Island, Mansions & Finger-Lickin’ Lobster Lunch and Western Acadia Park, Antique Cars and Lobster Combo so you don’t board the ship without having tasted Maine’s most famous food.

3. Alexander + Roberts

Departing from Boston in September and October, Alexander + Roberts’ newest ship—mv Victory II, built for 202 passengers—travels on the “Historic New England” itinerary to lesser-trodden ports in Massachusetts, including Provincetown (history buffs will love the Mayflower Compact) and Martha’s Vineyard (summer playground for many Northeasterners, sprinkled with gingerbread cottages and charming lighthouses); as well as Maine’s Kennebunkport (home to shipbuilding traditions). In Newport, Rhode Island, take ShoreTrips’ Ocean Drive and the Newport Mansions tour—prepare to be wowed. Or, literally Eat Your Way through Portland via ShoreTrips. 

4. American Cruise Lines

No more than 100 guests are onboard each American Cruise Lines voyage. Departing from Boston; Portland, Maine; New York City; and Providence, Rhode Island; each New England itinerary spans between eight and 11 days, allowing ample time for lobster feasts, marveling at fall foliage and strolling down cobblestone streets. While dates vary for each itinerary, the cruise line’s New England season runs from June to mid-October, with sails on American Constitution, American Star and Independence. Two ShoreTrips walking tours in Boston explore Freedom Trail and the North End for a deeper dive into New England history.

5. Blount Small Ship Adventures

Sailing on two 83-passenger ships (The Grand Caribe and The Grande Mariner), Blount Small Ship Adventures keeps things simple with just one departure port for its New England sails (Warren, Rhode Island). Next year’s cruises sail out of New York City. Before boarding, take a ShoreTrips’ food tour of the Big Apple, such as the “Eat Your Way Through Manhattan” or “A Taste of Brooklyn” tours. Between June and August, a six-night “Islands of New England” sail travels to seven ports, including Block Island, Rhode Island (home to the stunning clay cliffs of Mohegan Bluffs); and Cuttyhunk Island (just off Cape Cod, it’s the first English settlement of New England and the outermost of the Elizabeth Islands).

6. Pearl Seas Cruises

New to Pearl Sea Cruises is its “Maine Coast and Canadian Harbors” cruise, a seven-night journey each May and October on the 210-passenger Pearl Mist up Portland, Maine’s postcard-perfect coast into New Brunswick, Canada (St. Andrews and St. John). Stops off the beaten path include Campobello Island, the former summer retreat for President Franklin D. Roosevelt and his family. Or, book the 10-night “Canada and New England Fall Foliage” sail—also on Pearl Mist—where you’ll swear you’re surrounded by calendar images as the leaves are that stunning. The final two days of the sail, departing from Quebec City, are spent in Maine’s Bar Harbor and Portland where, with ShoreTrips, a private Meander the Southern Maine Coast tour for your group is at your own pace and taps into your personal interests for a highly customized experience.

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