Portland of the east

Portland Maine Harbor

If you’re anything like me, you’re already planning your travel for the year. And if you are, better add Portland, Maine, to your list.

I picked Portland because it seemed to have the best of both worlds – idyllic, water-front lighthouses and small town vibes + culture like art galleries, live music and top notch food. When I learned my mom had always wanted to go to Maine, too, it was settled!

Before we had even booked plane tickets (fyi flying to Maine is crazy expensive; Boston is way cheaper and just an hour and a half drive away!), I locked down our stay at The Mercury Inn. I fell in love with the mid-century modern and cozy place while researching, and in person the beautiful rooms, charming neighborhood, amazing hosts, and delicious food did not disappoint. The location was also amazing – one direction and we’re at a farmer’s market, the other and walking around downtown Portland. All of these superlatives do not even do it justice; just go there.

One thing that surprised me was how artsy the town was. I had pictured Maine to be a Life-Size Ralph Lauren catalogue, but it turns out Portland is home to art and film schools…so creativity abounds! Definitely nothing cookie cutter or preppy about the places and people, which I loved. Everywhere we went, friendly locals like a neurosurgeon on a Tinder date and a bartender who skis to work in the winter openly chatted with us about their lives and favorite places. Here’s what we did, with my favorites linked below!

Mercury Inn Bed and Breakfast Portland Maine



Eventide Portland Maine Seafood Restaurant

Lobster Roll Maine Food Truck


  • Oysters, Tuna Tartare and Cucumber Gimlet at Eventide
  • Fish tacos at El Rayo – I was suspicious about their “authentic Mexican” claim, but these are now my #2 favorite fish tacos (#1 goes to Duke’s in Malibu).
  • Gluten-free, dairy-free pizza at Otto (Yes, my mom is quite the trooper.)
  • Lobster Roll at the Bite Into Maine food truck – with gluten-free buns!
  • Bam Bam Bakery for Earl Grey Cake. Gluten-free and vegan, of course.
  • Duckfat for…duckfat fries.
  • Holy Donut


Tandem Coffee Portland Maine


  • Bard Coffee. My favorite! Seriously regretting not buying their beans.
  • Tandem Coffee. Cool space; acidic coffee, though – not my thing.


Maine Craft Distilling Portland Liquor

Fizz House Portland Maine

Portland Maine Breweries Bayside

Rising Tide Brewery Portland Maine


  • Vena’s Fizz House (non-alcoholic)
  • Bearded Lady’s Jewel Box. As recommended by Otto’s bartender. Really cool, slightly hidden space with speakeasy vibes (you have to be looking for it, or, like my mom, curiously peering inside every dark door with music playing inside). Here we met another loverly bartender who was actually Zach Galifianakis. I swear.
  • Breweries. Maine Craft Distilling (the best!), Rising Tide (Maine’s beers have a grassy taste, if you’re into that sort of thing), and Urban Farm Fermentary are all within walking distance of each other.


Imagine Maine Portland Shopping



Portland Maine Sailing

Sailing Portland Maine

Paddleboarding Portland Maine Beach


  • Walk around Downtown Portland
  • Ride bikes (from Gorham Bike & Ski) around Back Cove, stopping at the beach for reading and shell picking in the sand.
  • Portland Museum of Art – Free Admission Friday!
  • Farmer’s Market
  • Explore lighthouses in South Portland
  • Sailing at sunset. Freezing and worth it! If you can book one of the yoga or live music sails, too, do it.


thank you maine portland documentary school poster

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