Portland Head Light
Portland Head Light / iStock.com / fotoguy22
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Lobster roll
Lobster roll / iStock.com / rez-art
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Exchange Street
Exchange Street / Greater Portland Convention & Visitors Bureau
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Old Port
Old Port / Chris Lawrence
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Harvest on the Harbor
Harvest on the Harbor / Greater Portland Convention & Visitors Bureau
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Portland, Maine
Port
Deal Expert / Travel Blogger

Portland’s cool factor has grown in recent years, with many chefs, plus brewers and distillers, starting new businesses in and around the picturesque port town. The cruise ship terminal puts you within walking distance of its hippest neighborhoods. Actually, you’ll be within walking distance of most everything — the city of less than 65,000 people is pleasingly compact.

What We Love

The Old Port: This area, with its cobblestone streets and well-preserved Victorian buildings, has been beautifully restored and has everything from souvenir shops to indie boutiques to trendy watering holes.

Farmers Market: Held Wednesdays in the Old Port and Saturdays in Deering Oaks Park, the market has stands packed with local bounty. In late summer, find the cherry tomato bar, where the farmer lets you sample before building your own pint.

Best Known For

Lobster: The beloved crustacean might as well be the city’s mascot. You’ll see the traps along the waterfront and very likely eat a lot of it.

Portland Head Light: Built in 1791, the lighthouse in Portland Harbor was the first in the United States (and said to be the most photographed in the world). Take the pretty cliff walk that meanders along the sea.

Who It's Best For

Foodies: Portland has the second highest number of restaurants per capita (after San Francisco), ranging from vegan Thai to burgers and duck-fat fries to classic seafood dishes.

Craft Beer Aficionados: There are 39 breweries in Portland (plus dozens more in the rest of Maine) with many tasting rooms and beer gardens in town. Try the Maine Brew Bus if you want more structure to your tastings — and a designated driver.

Don't Say We Didn't Warn You

Cloudy Skies: New England’s weather can be unpredictable, with chilly, misty days during prime summer months that could thwart dreams of coastal hikes.

Reservations Required: Even with so many restaurants, tables fill up fast. It’s not uncommon to arrive for dinner at 9 and be told there’s still an hour-long wait.