Old Port - The Old Port in Portland, Maine is a charming historic area with cobblestone streets and shops offering clothing, gourmet food, and souvenirs. It’s also a popular nightlife destination with pubs, breweries, and bars attracting younger crowds. The dining scene is fresh and vibrant.

Casco Bay Lines Ferry Terminal - Casco Bay Lines, also known as the Casco Bay Island Transit District (CBITD), is a public transportation company serving the residents of the Casco Bay islands. These islands include Peaks Island, Little Diamond Island, Great Diamond Island, Diamond Cove, Long Island, Chebeague Island, and Cliff Island.

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

Maine Narrow Gauge Railroad Company and Museum - Founded in 1993, the Maine Narrow Gauge Railroad Co. & Museum is located in the former Portland Company Marine Complex. The collection includes passenger and freight equipment, as well as artifacts from the 2 ft (610 mm) narrow gauge railways that operated in Maine in the late 19th and early 20th centuries. The organization runs a 1 1⁄2-mile (2.4 km) railroad along the Casco Bay waterfront, parallel to Portland’s Eastern Promenade, using historic steam and diesel locomotives and restored coaches for passenger services.

Portland Observatory - The Portland Observatory, a historic maritime signal tower at 138 Congress Street in Portland’s Munjoy Hill area, was built in 1807 and is the only known surviving tower of its kind in the United States. It enabled two-way communication between ship and shore using a telescope and signal flags, several hours before an incoming vessel reached the docks. Designated a National Historic Landmark in 2006, it is now a museum managed by a local nonprofit and open to the public. The tower’s operations were funded by annual fees from shipping merchants, who paid to have their flags stored and hoisted when their ships were sighted. A telephone was later installed, extending the tower’s use until 1923, when engine-powered vessels and radio communication made it obsolete.

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

Portland Museum of Art - The Portland Museum of Art (PMA), founded as the Portland Society of Art in 1882, is the largest and oldest public art institution in Maine. It is situated in the downtown Arts District of Portland.

Victoria Mansion - Also known as the Morse-Libby House or Morse-Libby Mansion, Victoria Mansion is a notable example of American residential architecture in downtown Portland. Its brownstone exterior, elaborate interior design, opulent furnishings, and early technological conveniences offer a detailed look at lavish 19th-century American living. It was declared a National Historic Landmark in 1971 for its architectural significance as a well-preserved Italianate mansion.

• Driver/guide
• Tour

• Food and beverages
• Gratuities (suggested)