Portland, Maine | City Guide


After a few years of being "up and coming", Portland has arguably found its sweet spot. In my very humble opinion, it is one of the best cities in the country. A bold statement, I realize, but also one that's hard to argue once you consider the food, beer, ocean views, close proximity to the beach, and all the #wicked nice people. It's also easy to get to, easy to navigate (it's very small), and just so cute (hiiiii cobblestone streets). I digress. Portland is great and you should go and these are things you should consider/do/eat/drink/revel over:

take note

  • Portland is Maine's largest city, but it's still pretty small. While you can walk the entire Old Port area in about 20 minutes, you can still enjoy many of the perks of a big city.

  • What's the Old Port, you say? It's the section of downtown Portland that runs along the waterfront. It's where most (all?) the fun stuff happens.

  • You can fly into PWM, which, if you’re used to larger transportation hubs, is truly a blessing of an airport. From there, it's about a 10-15 minute drive to the Old Port. If you're coming from Boston, you can also take the Amtrak up from North Station, or catch a bus from South Station.


Visit the Portland Headlight - A must see when in Maine, mecca of lighthouses. Visit the country’s most photographed, and the state’s oldest lighthouse (it’s been LIT since 1791). While it’s not technically in Portland, it’s just a quick drive away in the neighboring (and beautiful) town of Cape Elizabeth. The lighthouse is located in Fort Williams Park, and entrance is free. It’s open year round from sunrise to sunset.
Walk through Portland’s Arts District where you’ll find cultural spots like the Maine Historical Society, Museum of African Culture, Portland Museum of Art and the Children’s Museum and Theatre of Maine. The Arts District also houses the Maine College of Art (MECA) as well as attractions like the Salt Institute of Documentary Studies, Cross Insurance Arena, the renovated State Theatre, and the Portland Stage.
Take the ferry out to Casco Bay's islands - The Casco Bay Lines ferry regularly departs Portland throughout the year, and drops off at Peaks Island, Little Diamond Island, Great Diamond Island, Diamond Cove, Long Island, Chebeague Island, and Cliff Island. While each island is unique, they all offer beautiful coastal views and, for the most part, subscribe to a much slower pace than the already slow pace of Maine itself.
Go to the beach - There are some truly beautiful beaches within the Portland area. Some of my favorites include: Crescent Beach in Cape Elizabeth, Higgins Beach, Pine Point, Fort Williams Park, and Ferry State Beach.
Go shopping - The Old Port is filled with cute boutiques and artisan shops. You’ll find everything from locally crafted home goods and furniture to brand name stores. With unique finds on every corner, there’s something for everyone.

eat & drink

Eventide Oyster Company - First of all, it’s an aesthetic dream with beds of oysters lining the bar, a beautiful turquoise blue wall imitating the ocean. But the real show stopper is the food. Their eclectic menu changes frequently. Hopefully they’re still serving the roasted oysters when you go because they’re just about the best thing my tastebuds have ever known.
The Honeypaw - Owned and operated by the same team as Eventide, The Honeypaw brings a delicious and wildly creative asian fusion flair to Portland’s food scene. It’s been featured in the New York Times, and dubbed ‘Maine’s restaurant of the year’ by Eater, so you know it’s good. Grab a seat at one of the communal tables, and order the Vietnamese Masa Crepe (remember what I said about creative?).
Duckfat - It’s been featured all over the place, including The Zimmerman List and Chopped - and for good reason. It’s certainly on the smaller side, with 32 seats, and you can almost always count on there being a wait (they don’t take reservations). Don’t sleep on the cone of Belgian-style French fries cooked in duck fat and served with dipping sauces (my favorite is the truffle sauce).
J’s Oyster - Locally loved, with an ocean front view and buckets (BUCKETS!) of clams. PS. My mom claims she ate the best lobster roll of her life here (she’s eaten a lot of lobster rolls). I tasted it - I don’t disagree.
Standard Baking Co. - Family owned, and busy busy busy in the mornings (always a good sign) this bakery serves artisans baked goods and the best damn croissant outside of France that I’ve ever had.
High Roller Lobster Company - Not all lobster is created equal. I’m here to nudge you away from the sponsored Yelp restaurants, and towards places like High Roller. Their menu features everything from the classic roll to the lobster grilled cheese. It’s all delicious.
Empire Chinese Kitchen - There’s Chinese restaurants, and then there’s Empire. This place is next level with their lobster fried rice, edamame dumplings, and Chinese eggplant, and pretty much everything else on their menu. The drinks are fun too!


Portland Harbor Hotel - Nestled in the heart of the Old Port, Portland Harbor Hotel is beautiful and cozy and pretty much everything you’d want in a hotel.
Mercury Inn - A bed and breakfast in a historic Victorian home. It’s stylish, located in a beautiful neighborhood, and dedicated to sustainable living.
The Press Hotel - Located in the Portland Press Building, and just steps from the Old Port, The Press Hotel was Portland’s first boutique hotel. It features farm to table dining, a spa, complimentary bicycles during the summer months, an art gallery, and more.

Gina SpinelliComment