Massachusetts Cruise from Boston — 16 Days

Boston, USA

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, USA

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.

Bath ME, USA

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.

Boothbay Harbor ME, USA

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.

Bar Harbor, USA

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.

Bangor ME, USA

Bangor sits on the Penobscot River, where Maine’s lumber boom once made it a major seaport. Today, its brick downtown, riverfront paths and historic homes reveal a quieter side of Maine. The Bangor Public Library is a striking landmark; Stephen King fans may recognize locations tied to his work. For a full day beyond town, drive to Acadia National Park, where granite coastlines and carriage roads reward unhurried exploration.

Rockland ME, USA

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.

Portsmouth NH, USA

Portsmouth is a New England port with a long maritime history and a lively, walkable center. From the waterfront, follow the streets to Market Square, where brick sidewalks, independent shops and cafés anchor downtown. At Strawbery Banke Museum, preserved homes trace four centuries of life in this former seaport. Across the Piscataqua River, the Portsmouth Naval Shipyard sits in Kittery, Maine—a reminder that this harbor remains working water.

Gloucester MA, USA

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.

Provincetown MA, USA

At Cape Cod’s outermost tip, Provincetown rewards a leisurely day ashore with sea air, history and a lively main street. Climb the Pilgrim Monument for a sweeping view, then explore Commercial Street’s galleries, cafés and independent shops. Whale-watching boats leave the harbor for waters frequented by humpbacks, while nearby dunes offer a quieter side of the Cape. Allow time for seafood and the town’s Portuguese-influenced culture; Provincetown is best enjoyed without rushing.

Newport RI, USA

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, USA

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.

Nantucket MA, USA

Nantucket is a small island 30 miles south of Cape Cod, where maritime history remains part of daily life. From the harbor, head for cobbled streets and handsome gray-shingled houses. The Whaling Museum traces the 19th-century trade that once made Nantucket one of America’s richest towns. Beyond town, lighthouses and broad Atlantic beaches reward a bicycle ride or a slower afternoon.

Martha's Vineyard Island, USA

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.

Cape Cod Canal, USA

Transit the Cape Cod Canal and watch New England’s coast redraw itself. This 17.4-mile waterway cuts across Cape Cod’s narrow neck. It links Cape Cod Bay with Buzzards Bay, avoiding the longer route around the peninsula. Opened in 1914, it remains one of the region’s defining engineering works. From the deck, look for the Bourne and Sagamore bridges, shore paths, and tidal currents that shape every passage.

• Land Tour (Land Tour)
• Land Tour (Land Tour)

Plymouth MA, USA

Plymouth rewards visitors who look beyond the famous rock to a town shaped by sea and history. At Plimoth Patuxet Museums, recreated seventeenth-century settings and Wampanoag-led interpretation offer a fuller account of colonial beginnings. On the waterfront, Mayflower II recalls the 1620 voyage, while nearby streets lead to independent shops and harbor views. Allow time for Burial Hill and the town’s seafood restaurants; Plymouth’s compact center makes an easy day ashore.

Boston, USA

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.