Portland, Maine Travel Guide: Where To Stay, Eat, and Drink

The city offers chill vibes, great food, and some jaw-dropping scenery.

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A trip to Portland, Maine, is much more than flannels and Subarus—although you'll come across plenty of those, too. Maine's largest city, surrounded by water, is as picturesque as they come, with quaint cobblestone passageways and Victorian dream homes. Breathe in the fresh New England air while exploring the Old Port, sift through treasures at the vintage shops, and eat your way through the city's award-winning restaurant scene. More oysters? Don't mind if I do.

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WHERE TO STAY

Attention history buffs (and those who just appreciate great hotels): In the very center of Portland lies The Press Hotel, once home to the printing plant of the Portland Press Herald. The building, which dates back to 1923, has been totally transformed into a modern 110-room boutique hotel. The decor's wood paneling and ambient lighting is a nod to a 1920s writer’s office. One of the hotel's coolest features? A permanent art gallery on the lower level featuring local Maine artists.

BOOK IT

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WHAT TO DO

FOR THE ART LOVER: For years, artists have flocked to Maine to harness the region's restorative powers, establishing artists’ colonies, schools, and an overall pretty rad creative scene. Visit the Portland Art Museum, home to an extensive collection of American, European, and contemporary works from greats, including Matisse, Picasso, and Edward Hopper. If the weather cooperates, take a day trip (about an hour's drive) to check out the Coastal Maine Botanical Garden's stunning grounds, decorated with sculptures (part of the garden's permanent art collection), or one of their seasonal exhibitions.

FOR THE OUTDOORSY TYPE, BY LAND: If you have a long weekend, designate one day to venture outside of Portland. Rent a car (to fit in, lock down a Subaru), and head 30-minutes north to the towns of Pownal or Freeport for an adventure with L.L. Bean’s Discovery School. Night-owls may find the the full-moon hiking tour enticing, while those looking for something a little more meditative may prefer a guided yoga hike, during which you’ll tackle a local trail, stopping at scenic locations along the way to practice a few asanas.

AND BY SEA:
One of the best ways to see Maine? By boat. If you’re there summer through early fall, try a whale watching excursion that will put you in the middle of the action. For non-peak months opt for a windjammer cruise. Bring your own wine and cheese, a wool blanket, and your friends and saddle up to the sea.

FOR THE VINTAGE VETERAN: Get your throwback fix at the Portland Flea-For-All or Moody Lords Vinyl and Vintage. For unique finds that also happen to be new, stop by non-vintage More & Co. which sells locally crafted artwork, kitchen wares, and clothing.

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WHERE TO EAT

FOR THE SEAFOOD LOVER: Is it really a trip to Maine, if you don't eat some sort of shellfish? We think not. Therefore, you must check out The Shop by Island Creek Oysters. Swing by the bar, have a chat with the knowledgeable “oystenders,” and order up a few dozen fresh mollusks, caviar (if you’re feeling fancy), and then wash it all down with a local beer, champagne, or wine on tap.

FOR THE FARM-TO-TABLE FAN: Another trendy option is Drifters Wife. The restaurant originally began as a natural wine shop in 2015, then started serving food to accompany (and soak up) the celebrated wine list. Now a full-scale restaurant (with the original wine shop just next store), the menu is small but mighty, and changes daily, featuring innovative dishes using fresh caught seafood, proteins, and local veggies.

FOR A CELEB SIGHTING: Boasting a buzzy atmosphere and a line out the door (it’s well worth the wait, trust), Izakaya Minato is a must-visit for some amazing Japanese food with a twist. Sample a little bit of everything from the shared plates menu, like the tuna poke with avocado, garlic, and sesame oil; Japanese fried chicken; beef short ribs; and the kimchi fried rice. Celebs you said? Regulars include Willem Dafoe.

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WHERE TO DRINK

BUCHA: Master kombucha brewer Reid Emmerich’s new kombuchery, Root Wild Kombuchery, specializes in kombucha (duh). Plus, they've partnered with the owners of Lone Pine Brewing, one of the fastest growing breweries in Maine, to add cool craft beers to their offerings.

BEER: If you haven't had enough of the fermented stuff already, head over to one of the MANY Maine brewery’s that have taken root in town. Better yet: Take a ride on the Maine Brew Bus. Oxbow Brewery, Bissell Brothers, Lone Pine Brewery, Allagash, and Maine Beer Company in Freeport are just a few spots that top my list.

SPIRITS: For a classic cocktail and a cool vibe, head over to Portland Hunt and Alpine Club. Cozy up to the bar and order the refreshing Lavender Collins made with lavender-caraway, lemon, and grenadine, followed by the ever-changing daily punch. When late-nite hunger strikes, choose something from the snacks menu—perhaps the house made soft pretzels and the popcorn sprinkled with green chile powder, butter, and parm?

Make sure to pencil in a stop at Blyth and Burrows, often I.D'd as one of the best cocktail bars in Maine. Their vintage-inspired bar is influenced by the region’s maritime history and their name pays tribute to two captains who captured the HMS Boxer off the coast of Maine in 1813. Order The High Priestess, with pineapple-chamomile pisco, pamplemousse, and lemon, or the innovative Walrus & The Carpenter, made with gin, kelp & oyster shell dry vermouth, and aquavit.

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