The Old Port in Portland, Maine is a quaint historic district with cobblestone streets and shops selling clothing, gourmet food and souvenirs. It’s also a hot spot for nightlife where pubs, breweries and bars draw the younger crowds. There is also a fesh and lively dining scene.

Casco Bay Lines (also known as the Casco Bay Island Transit District, CBITD) is a publicly run transportation company that services the residents of the islands of Casco Bay. These islands include Peaks Island, Little Diamond Island, Great Diamond Island, Diamond Cove, Long Island, Chebeague Island and Cliff Island.

Shipyard Brewing Company, founded in 1994 is a brewery and soft drink manufacturer in Portland, Maine. Shipyard is the largest brewer in Maine and is the fourth largest microbrewery in New England.

The Maine Narrow Gauge Railroad Co. & Museum is located and operates out of the former Portland Company Marine Complex, the organization was founded in 1993. The collection consists of passenger and freight equipment, as well as artifacts from the 2 ft (610 mm) narrow gauge railways that ran in the state of Maine in the late 19th century and early 20th century. The organization operates a 1 1⁄2-mile (2.4 km) long railroad that runs along the waterfront of Casco Bay and parallels Portland's Eastern Promenade. Historic steam and diesel locomotives and a variety of restored coaches are used to run passenger services on the railroad.

The Portland Observatory is a historic maritime signal tower at 138 Congress Street in the Munjoy Hill section of Portland, Maine. Built in 1807, it is the only known surviving tower of its type in the United States. Using both a telescope and signal flags, two-way communication between ship and shore was possible several hours before an incoming vessel reached the docks. The tower was designated a National Historic Landmark in 2006; it is now managed by a local nonprofit as a museum, and is open to the public. The Portland Observatory is the only remaining maritime signal station in the United States. Tower operations were paid with annual fees collected from shipping merchants, who purchased the right to have their flags stored in the building and hoisted up its flagstaffs when their ships were sighted. A telephone was eventually installed, extending the tower's function until 1923, when the reliability of engine powered vessels and communication by radio made it obsolete.

The Wadsworth-Longfellow House is a historic house and museum in Portland, Maine, United States. It is located at 489 Congress Street and is operated by the Maine Historical Society. It was designated a National Historic Landmark in 1962, and administratively added to the National Register of Historic Places in 1966.

The Portland Museum of Art, or PMA, is the largest and oldest public art institution in the U.S. state of Maine. Founded as the Portland Society of Art in 1882 It is located in the downtown area known area The Arts District in Portland, Maine.