City Guide: Things to do While Boating in Portland, Maine

Located between Bar Harbor and Kennebunkport, Portland offers a scenic setting of lobster boats, lighthouses, long strands of sandy beaches and stunning views of Casco Bay and the Atlantic Ocean. Whether you’re in town for a day, a long weekend or an extended stay at a private boat lift rental, there’s bound to be something to entertain the whole crew.

A historic fishing and commercial shipping port, the Port of Portland is the second-largest tonnage port in New England. Old Port, popular for nightlife and its 19th-century architecture and cobblestone streets, offers restaurants, bars and boutiques. The Portland Waterfront Historic District is on the National Register of Historic Places and overlooks the Fore River.

Let’s get started exploring Portland!

Lighthouses

Photo: Portland Head Light / Wikimedia

If you’re a fan of nautical beacons, you’ll love the lighthouses of Portland. Spend a day exploring the area from a private boat dock for rent. The 1791 Portland Head Light (located in Fort Williams Park) is 102 feet tall and the oldest in Maine. It makes a striking selfie spot with its white conical tower and black gallery and cupola set against the rocky shores of the Atlantic. That red roof on the keeper's house makes the whole scene pop. 

The 30-foot-tall Portland Breakwater Light, also called Bug Light is located in Bug Light Park. It was first built in 1855 and then a new one was built in 1875. The conical granite block caisson-style structure features Greek Revival architecture and intricate detail.

The sparkplug-style Spring Point Ledge Lighthouse was built in 1897. It’s 54 feet tall and the only one of its type that visitors can walk to. Private tours are available by reservation.

Two Lights State Park

Photo: Wikimedia

Visit Two Lights State Park for fishing, picnicking and hiking along the shoreline, rocky cliffs and impressive headlands. The park has 41 acres with views of the Atlantic Ocean and Casco Bay. Two lighthouses, built in 1828, made a unique addition to the area. One had a flashing beam and one had a fixed beam to warn boaters of the rocky shores. One of the lighthouses, the Cape Elizabeth Light Station, is still active and in service. The other is a private home. Edward Hopper’s “Lighthouse at Two Lights” painting is based on the area. Check out the view from a private boat lift for rent.

Victoria Mansion

Photo: Wikimedia

Victoria Mansion, a National Historic Landmark, is an excellent example of Italian villa-style architecture. Also known as the Morse-Libby House, it was built from 1858 to 1860. The mansion features the 19th-century opulence of Italian trompe l’oeil murals, gilded accents, intricate woodwork and original furniture. It was the home of luxury hotel operator Ruggles Sylvester Morse and his wife Olive. Take tours and attend events like ballet performances and historic storytelling. Don’t miss the Carriage House Museum and Shop.

Portland Museum of Art

Photo: Flickr/Paul VanDerWer

Founded in 1882, the Portland Museum of Art is located in the downtown arts district. Spend a day away from the private boat lift rental viewing contemporary art, photography, sculptures, German expressionist prints and an outdoor sculpture park. The museum’s collection includes more than 18,000 pieces of artwork from artists such as Claude Monet, Andy Warhol, Mary Cassatt, Renoir, John Singer Sargent and Winslow Homer.

Peaks Island

Photo: Wikimedia

An island in the middle of the bay? Yes, please! Peaks Island is a quick ferry ride from the Portland waterfront. The small 740-acre island in the middle of Casco Bay offers beaches, cafés and the Fifth Maine Regiment Museum, which gives a look into island history from early settlement to its role in WW II in an 1888 building. Once called the Coney Island of Maine, the island is a popular leisure destination and residential area for artists and retirees. Take a golf cart tour, ride a bike, go kayaking or just enjoy the views from the WW II fort at Battery Steele.

Maine Narrow Gauge Railroad

Photo: Wikimedia

Get to know the local scenery on a train ride along the Portland coast. The Maine Narrow Gauge Railroad is a historic train that rolls along a two-foot-wide track. On this three-mile 40-minute ride, you’ll learn about railroad and local history. The kids will love this fun adventure from a private boat dock rental.

International Cryptozoology Museum

Photo: International Cryptozoology Museum (Facebook)

Calling all Bigfoot fanatics. The International Cryptozoology Museum explores the mysteries of mermaids, the Loch Ness Monster, the Abominable Snowman, Bigfoot and more. Founded in 2003, it overlooks the Fore River and makes a unique excursion from a private boat slip for rent.

Peruse displays on native art, scientific specimens, folk traditions, artifacts and oddities Check out the Sasquatch Revealed exhibit and the 5.5-foot long coelacanth “living fossil” fish. Cryptozoology is the study of hidden, unknown and odd animals, in case you hadn’t already figured that out.

We hope you’ve found a few new addresses to add to your Portland itinerary. Let us know what you find fascinating!