Portland, ME: The Perfect Weekend Getaway

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Advisor - Maggie Pecorino
Curated By

Maggie Pecorino

  • Portland, Maine

  • Digital Nomad Travel

  • City Travel

  • Nature Escapes

  • Outdoors

  • Sightseeing

  • Local Food

road through fall foliage
Curator’s statement

Portland is such an underrated city. Its manageable size and quaint, laidback vibes make it a wonderful escape for anyone looking to slow down, take a breath, and enjoy some fresh ocean air — plus tons of yummy food & drink, of course. Clocking in at a six-hour drive from New York, and only two hours from Boston, Portland makes a perfect choice for your next lowkey weekend getaway.

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Where to stay in Portland, Maine

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Things to do in Portland, Maine

Rocky beach view

Get out on the water:

No shortage of boat tours and excursions to choose from in this historic port city! Some offer local/historical insights, while others are designed for pure leisure and coastal views. (Contact me for a list of of detailed options.)

For a very Maine time:

Lucky Catch Cruises’ 90-minute tours offer an authentic, hands-on look at one of New England's most important industries: lobstering. This fun & fascinating educational journey into the heart of Maine culture is run by a company of legit lobstermen — when not entertaining passengers, they're out on the water, reeling in their own traps.


Portland’s small size (< 70,000 people!) means thrift shops are ripe with hidden gems. I also found shopping to be quite affordable when compared with larger cities. Check out: Weekend Vintage (I adore this place), Portland Flea-for-All (10,000+ sq. Feet), Moody Lord Vinyl/Vintage, Little Ghost

Weird Museums:

Put your hunting caps on and check out the International Cryptzoology Museum in dedication to hidden/questionable animals such as Bigfoot, the Yeti, etc.. Then make your way to the Umbrella Cover Museum, with exhibitions dedicated to the appreciation of the mundane in everyday life.

Wander around Old Port:

This area of downtown is filled with cobblestone streets and 19th-century brick buildings. Bring your camera! You’ll also find some of the city’s best shopping and bar-hopping options.

Portland Farmers’ Market:

Local agriculture is a key part of the Maine way of life. Here you will find 40+ farmers, cheesemakers, beekeepers, bakers, florists, etc.. set up in Deering Oaks Park. (Weds & Saturdays in summer; Saturday only in winter.)

Enjoy the Eastern Promenade at Sunset: 68-acre public historic park with backdrops of the harbor and Casco Bay. Super clean. An easy walk from Old Port.

Day Trips:

Peaks Island is a 720-acre oasis of peace just a 15-minute ferry ride away from the Portland Harbor. There’s not much to do but enjoy the fresh air and ocean breeze — and that’s how the island’s 1,000 residents like it. Most visitors get around by foot or bike, though you can also rent a golf cart upon arrival.

Places to eat & drink in Portland, Maine

A red lobster on a plate in Maine.


Becky’s Diner:

A Portland waterfront staple since 1991. Cozy old-school diner vibes. Very affordable. Family-run. Loved by locals and tourists alike.


Belgian-style frites fried in duck fat. Crispy on the outside. Creamy inside. Try all the sauces… and get a milkshake to dip into while you’re at it. (Popular tourist spot — expect a short wait.)

Hot Suppa:

Really dank Southern Comfort food. Small joint — expect a bit of a wait on weekends. Perfect for a cold, sleepy brunch.

The Holy Donut:

Mashed potato donuts, mashed potato donuts, mashed potato donuts. Trust.

Highroller Lobster Co:

Famous, unpretentious lobster joint dishing out fresh rolls and other yummy goodness like lobster Mac & Cheese.

Fore Street Restaurant:

Upscale New American fare cooked over an open wood-fire grill & spit. The house-made sourdough steals the show. I enjoyed a solo birthday dinner here four years back, and I still recall that meal with pleasure. (Reservations required.)



BREWERY ALERT. This one’s for fellow fans of barrel-aged ales and funky brews. Oxbow is heaven. I’d make the 6-hour drive up to Portland just to buy bottles.

Root Wild:

Seriously delicious hard kombucha in an array of creative flavors. Bright and clean space.


Portland’s craft beer scene would be different without Allagash and their huge space just outside the city center. This one is definitely worth a tour! Expect food trucks and something tasty to sip for everyone. (Tip: Don’t skip their brewery neighbors.)

Cocktail Mary:

LGBTQ+ community hub chock full of great vibes and unique cocktails. Check out their Instagram for updated events like DJ sets, drag shows, pop-up shops, and more.

Need to Know

This guide is part of our ongoing series on travel to Portland.

Advisor - Maggie Pecorino

Travel Advisor

Maggie Pecorino

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