Massachusetts Cruise from Boston — 12 Days

Boston, Massachusetts

Boston rewards visitors who like their history close at hand and their cities easy to explore. From the waterfront, follow the Freedom Trail to landmarks of the American Revolution, including Faneuil Hall. Beacon Hill’s brick streets, the Public Garden and North End cafés reveal distinct sides of the city. Make time for harbor views and New England seafood; Boston’s pleasures are as tangible as its past. Its museums and universities give the compact city a lively, modern edge.

• Land Tour (Land Tour)

Portland ME, Maine

Portland follows the Willamette River, with the Columbia to its north and Mount Hood on the eastern horizon. Begin downtown at Powell’s City of Books, a landmark independent bookstore spanning an entire city block. Visit the Japanese American Historical Plaza beside the waterfront, or head to Washington Park’s International Rose Test Garden. Food carts, craft breweries and seasonal produce give the city its distinctive taste. Allow time for the Columbia River Gorge, whose waterfalls and trails lie east of town.

Rockland ME, Maine

Rockland puts Maine’s working coast within easy reach, with lobster boats, granite piers and Penobscot Bay on its doorstep. At the Farnsworth Art Museum, paintings by Andrew Wyeth and other American artists offer a compelling counterpoint to the harbor. Walk the nearly mile-long Rockland Breakwater to its lighthouse, then return for fresh seafood along Main Street. Here, art and sea air give the day an unmistakably Maine character.

Bar Harbor, Maine

Bar Harbor is the gateway to Acadia National Park, where granite cliffs, spruce forests and coastal trails frame the Atlantic. Closer to town, the Shore Path follows the waterfront past elegant summer cottages and views across Frenchman Bay. Walkable streets lead to independent shops and restaurants serving Maine lobster and other local seafood. Take a boat trip for a different view of the islands, or explore Acadia’s carriage roads and mountain routes.

Boothbay Harbor ME, Maine

Boothbay Harbor puts Maine’s working coast within easy reach. Lobster boats share the water with schooners, excursion vessels and pleasure craft, while shops and seafood restaurants line the waterfront. Cross the 1901 footbridge for a quieter view of the harbor and its islands. In season, boat trips seek whales and seals; the Coastal Maine Botanical Gardens reward visitors ashore. Come for salt air, maritime history and a genuine small-town harbor.

Bath ME, Maine

Bath, Maine, sits on the Kennebec River, where shipbuilding has shaped this coastal city for generations. Its working waterfront and historic streets give the port a distinctly local character. Explore the Maine Maritime Museum for stories, vessels and skilled trades behind the state’s maritime heritage. Then stroll downtown, where independent shops, cafés and 19th-century architecture are close at hand. Bath suits travelers who prefer authentic history to a staged seaside scene.

Gloucester MA, Massachusetts

Gloucester is a working harbor with a history you can still see along its waterfront. Founded in 1623, this Cape Ann city built its fortunes on the sea, and fishing remains central to its identity. Visit Maritime Gloucester, watch boats return to port, or join a whale-watching trip into the Atlantic. Then explore nearby beaches, rocky headlands, and the artists’ colony of Rockport.

Coastal Cruising (Coastal Cruising)

Newport RI, Rhode Island

Newport rewards visitors who look beyond its famous mansions. This Rhode Island harbor town pairs Gilded Age grandeur with working waterfronts, historic lanes and Atlantic views. Tour The Breakers, the Vanderbilt summer home, then follow the Cliff Walk past oceanfront estates and crashing surf. Downtown, independent shops and seafood restaurants line streets shaped by centuries of seafaring trade. Allow time for a harbor sail or a visit to Fort Adams, where the coastline opens wide.

Martha's Vineyard Island, Oak Bluffs, Massachusetts

Martha’s Vineyard is more than a summer address. Its six distinct towns are reached by ferry from mainland Massachusetts. In Edgartown, white Greek Revival houses recall the whaling era. Oak Bluffs adds painted gingerbread cottages and a lively harborfront. On the western shore, Aquinnah’s clay cliffs frame broad Atlantic views. Make room for fresh seafood, independent shops, and the island’s easy pace.

Boston, Massachusetts

Boston rewards visitors who like their history close at hand and their cities easy to explore. From the waterfront, follow the Freedom Trail to landmarks of the American Revolution, including Faneuil Hall. Beacon Hill’s brick streets, the Public Garden and North End cafés reveal distinct sides of the city. Make time for harbor views and New England seafood; Boston’s pleasures are as tangible as its past. Its museums and universities give the compact city a lively, modern edge.