Frequently-departing commuter ferry run by Casco Bay Lines. Departs from the Old Port and trip takes about 20min each way. Beautiful views of Portland, the Island, and decommissioned Fort Gorges that sits in between.
Museum of Art
Large museum steps from the Westin hotel. Great collection spanning the ages.
Eastern Cemetery
Small historical cemetery running along Congress Street at Washington in the East End. Beautiful and quiet.
Wadsworth-Longfellow House
The historical home of Longfellow. Sits on Congress Street next to the Time & Temperature Building. Very well preserved and insightful tour. Includes admission to a historical museum attached to the home.
Deering Oaks Park
On the northwest corner of the peninsula sits Deering Oaks Park, a large open public park. Great for wandering and taking in the fall colo(u)rs.
Portland Head Light
A bit outside downtown Portland, you would likely need to rent a car, bike, or taxi. This historic lighthouse protrudes from South Portland and includes great views of Casco Bay. It's the most photographed lighthouse in America.
The Old Port
Interesting shops line Commercial, Fore, and Middle Street in the Old Port. Spend the morning wandering around the area to buy clothes, gifts, books, trinkets, etc.
State Theatre
Historic theater, opening in 2010 as a performing arts center - check the calendar of events to see who's coming to town!
Mackworth Island
Small island and bird sanctuary located just north of Portland accessible via causeway that connects to Falmouth. Great for a short hike if the weather's nice!