Portland Vacations

The largest city in Maine is a gateway for island hopping in summer, skiing in winter and a thriving cultural center year-round.

Renowned for the many outdoor adventures that are nearby, Portland, Maine, also offers visitors a large downtown arts district and a vibrant food culture.

Kick off your exploration in the Old Port. This historic district with cobblestone streets and converted Victorian warehouses contains many boutiques, galleries and restaurants. Visit the late 18th-century Portland Head Light lighthouse. Although the tower isn’t open to the public, you can still explore the small museum in the former Keepers’ Quarters, which is open seasonally. 

Portland’s creative side is seen in its many downtown museums and galleries. Discover three centuries of American and European fine and decorative art at the Portland Museum of Art. For music, dance and drama, visit the Merrill Auditorium and the Portland Stage theater.

After a tour of the town and its museums, go kayaking or take a boat cruise to explore coastal and inland waterways. On a warm day, swim in a clear lake, relax on the beach or go whitewater rafting down the Kennebec River. Take a short ferry ride out to the Casco Bay Islands, an archipelago off Portland’s coast. Visit the islands’ beaches, woods and villages. Peaks Island is the bay’s most populated island and has an artistic community. Walk its 4-mile (6.4-kilometer) Peaks Island Loop. In winter, go skiing in Sunday River and Sugarloaf, two skiing resorts within driving distance of the city.

Compact Portland is easy to navigate by car and public transport and on foot. There is a fee for parking in the downtown area, except on Sundays. In winter, check the nightly parking ban to avoid blocking snow plows.

The city is 310 miles (499 kilometers) from New York City and daily flights from there and Washington D.C. go into Portland International Jetport. As the city has a working port and cruise terminals, you can also get there and away by ship.

Guide to Exploring Portland

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