While Portland is a great destination regardless of where you live, I especially love that it’s such a short trip from Boston. A city that’s so close (an hour and a half or so by car) and can actually feel like you’re a flight away is the most ideal feeling for a weekend getaway. I can’t help but think of Portland as Maine’s version of Newport: there’s a lot of history and charm, with enough small shops and award-winning restaurants to keep you here for weeks—all located directly on the water. My favorite parts? The abundance of fresh oysters and lobster and the encouraged happy hours!
To Eat
- Drifter’s Wife – A current hot spot for a truly delicious meal. While you’re there check out the restaurant’s sister wine shop, Maine & Loire.
- Fore Street – A must! Reservations book up very far in advance but I think this is the best pick for quintessential Portland — farm to table ingredients, rotational offerings and a cozy, upscale vibe.
- Eventide – It’s worth the wait for this lobster roll alone! Trust me — the constant crowds of people don’t lie.
- Duckfat – Although deemed a tourist hotspot, the poutine at this quaint, yet well-known spot is really (really) great.
- Blythe and Burrows – The best craft cocktail bar I might have ever been too. You know those places where the bartenders are like artists? Like that, in a super cool speakeasy atmosphere.
- The Shop – Only the best oysters from the well-known Island Creek Oysters. Sit out on their open patio located up a few blocks from the bustle of downtown.
- Scales – Great location and views and a fantastic menu.
- The Holy Donut – Another Portland must! The Maine Blueberry is my favorite.
- Sur Lie – Great for happy hour and tapas.
To Stay
- Press Hotel
- The Danforth
- Portland Harbor Hotel
- Airbnbs – There’s a lot of great Airbnb options for Portland, including Airbnb Plus offerings. I suggest staying in walking distance to the Old Port, like here or here.
To Do
Wine Tasting – Portland may be known for its craft beer, but at the city’s newest wine bar, Grippy Tannins, you can enjoy a number of wines in an ultra chic and comfy setting.
Portland Museum of Art
The Portland Observatory
Boat Rides and Whale Watches – While there’s too many to list here, Portland offers many boat cruises and whale watches, if you’re interested in soaking up as much ocean-time as possible.
Live Music – My favorites were the Thirsty Pig and Portland Lobster Co.
Perkins Cove – A short drive out of the city will bring you to Ogunquit, Maine, home of Perkins Cove. Go here for a stroll along the cliff walk (also very Newport-esque), cute shops and multiple restaurants to indulge in casual summer food from whole lobsters to burgers.
Shopping
Flea-for-All – A large vintage market, fun to treasure hunt through.
Exchange Street – From clothing to souvenirs, ceramics and stationary, this busy little street has something for everyone. And when shopping gets exhausting, head into the Thirsty Pig or Blythe and Burrows for a craft beer or cocktail.
Pinecone and Chickadee – This fun-to-explore shop offers a variety of fun items, including VHS and Polaroid cameras!
Strata – Walk up a few blocks from the bustle of Old Port to the ‘Black Boxes’, where you’ll find this shop, a dream come true for the home chef in your life. The craftsmanship of this culinary knife shop and whetstone sharpening service is pretty impressive, even if you aren’t going home with a hefty Japanese knife.
Mulxiply x Campfire Studios – Located in the micro space next door to Strata, this space offering jewelry and leather goods from Mulxiply and ceramics from local brand Campfire Studios is bound to be the perfect spot to pick up something for a loved one, or yourself, on your trip.
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