Cruising Portland, Maine

All of the wonderful reasons why Maine is known as “Vacationland” are on full display in picturesque Portland. Cruisers will find breathtaking natural beauty, fun cruising grounds, fascinating maritime history, a lively arts district, and a nationally acclaimed culinary and craft-beer scene.

Things to Do

Casco Bay is a superb cruising ground, with more than 200 islands to explore. Great Diamond Island is a favorite among local boaters. Other popular stops include Harpswell Neck, Peak Island and Chebeague Island, where visitors can play nine holes at the historic and scenic Great Chebeague Golf Club. The bay itself is home to around 150 varieties of water birds and 850 species of marine life, including harbor seals, dolphins, porpoises and several whale species.

Numerous Portland-area landmarks are on the National Register of Historic Places. The 78-acre Eastern Promenade, designed by Frederick Law Olmsted, provides gorgeous views of the bay, especially at sunset. Dive into the area’s maritime history in nearby Cape Elizabeth at the Portland Head Light and museum. Commissioned by George Washington and first lit in 1791, it’s the oldest lighthouse in Maine. The 86-foot-tall Portland Observatory, built in 1807, provides stunning panoramas and insightful docent tours. A few blocks south, explore the 19th-century brick buildings along the cobblestone streets of the Old Port district.

Nearby is the Arts District, where creative energy abounds in numerous galleries, working artists’ studios and the renowned Portland Museum of Art. The First Friday Art Walk and accompanying live music series in Monument Square are a big draw from July through October.

Food and Drink

Portland has an outsize reputation as a foodie haven. Among its more than 60 breweries, Allagash Brewing Company is the most well-known for its Belgian-style ales, the Bite Into Maine food truck that serves mouthwatering lobster rolls, and the company’s James Beard Award-winning founder, Rob Tod.

Fellow winners Andrew Taylor and Mike Wiley helm Eventide Oyster Company, a refined restaurant serving 14 varieties of oysters daily, a delectable brown-butter lobster roll as well as other seafood dishes. Fore Street is a farm-to-table institution that books up two months in advance, changing its menu daily to capitalize on the freshest ingredients possible. Chaval brasserie pairs an exceptional vermouth selection with Spanish and French fare.

For more casual options, there is pizza with water views at Flatbread Company. Duckfat is popular for its poutine, frites and sandwiches. Becky’s Diner is a solid bet any time of day. And indulge in whoopie pie and wild Maine blueberry pie—two classic Maine desserts—at Two Fat Cats Bakery.  

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