Follow My Journey: 3 Days in Portland, Maine

Rachel Lewis, Dinogo Planet’s senior social media manager, recently enjoyed a weekend getaway with her wife in Portland, Maine. Here, she shares her favorite moments and what to consider before your visit.

I’ve always envisioned what a trip to Portland, Maine would be like, and it lived up to the classic image: rich lobster, coastal vibes, setting sail from the Old Port, and exploring local pottery shops. Though I had never been to Maine, my grandmother from Massachusetts had two pieces of advice for my long weekend with my wife: indulge in as much food as possible, and visit the beloved Cool As A Moose (and get her a mug for Christmas – you got it, Gramma). We arrived hungry and ready for souvenirs, and off we went.

I’m here to help you experience the same joy. Here are a few highlights from my unforgettable weekend in Portland.

What was your accommodation like? How was the atmosphere?

Located in the West End, The Longfellow Hotel is a recently opened boutique hotel committed to sustainability. On our first morning in Portland, we decided to try room service, ordering an iced oat milk latte for myself. It hit the spot, while my wife couldn't stop praising her breakfast sandwich—baked egg, spicy mayo, and pepper jack on an English muffin.

I was especially taken by the inventive mocktail menu at their dining spot, Five of Clubs. Finding enjoyable alcohol-free options while traveling sober (or sober curious, like me) can be challenging, but their 'functional cocktails' are remarkable. I enjoyed a Rosarium—bitter orange, earl grey, pomegranate—and a Vacationland Refresher—wild Maine blueberry, cardamom, lemon soda. The earl grey was a delightful welcome to the cooler months. 

The spa, Astraea, offers an infrared sauna (be sure to book it ahead of time!), providing a private space complete with a bathroom, rain shower, and sauna. They have various massage treatments available. We opted for Mindful Dreams, a soothing, rhythmic full-body massage ($145/person for 60 minutes). Enjoy a cup of peppermint tea and relish the blissful sensation as you unwind in your rejuvenated skin (I know that’s not exactly how it works, but that’s how it feels).

What was your favorite dish or drink?

I won’t even try to choose a single 'best' meal in Portland, but given its foodie reputation, you can count on a fantastic dining experience. Here are the standout dishes, snacks, and flavors we encountered.

Brickyard Hollow Brewing Company is a local favorite known for its gourmet pizzas, with locations from Freeport to Yarmouth (the original spot) and beyond. We opted for the cheese pizza, which was wonderfully simple: a 12-inch delight featuring a rich olive oil base. Next time, though, I’d like to try something more adventurous, like the blueberry pizza topped with Maine blueberries, rosemary ricotta, roasted shallots, and lemon zest.

Green Elephant, a vegetarian bistro, doesn’t accept reservations, so make sure to arrive at 11:30am when lunch begins. Treat yourself to deep-fried vegetarian spring rolls and king oyster mushroom tempura. If you're a vegetarian like me, you'll love dining in a place where you can confidently choose anything from the menu without worrying if the supposedly vegetarian option is truly meat-free. Be sure to try the ginger noodles for a flavorful kick (you can make it vegan by omitting the egg).

Another delicious lunch spot is Benkay, a Japanese restaurant and sushi bar. Try the teriyaki tofu; it’s quick, hot, and comes with a vibrant assortment of vegetables. For a satisfying dinner, we visited Black Cow, a burger joint. I enjoyed a veggie burger featuring a mushroom lentil patty, iceberg lettuce, pickled red onion, radish, and black garlic mayonnaise on their distinctive black cow bun.

If you need a snack break during your explorations in Portland, grab a donut from Holy Donut (the blueberry glaze is a must-try). For a quick breakfast on the go, Navis Café on Thames Street—just a block from the waterfront—offers tasty egg-white bagels and iced decaf vanilla lattes.

What was the most touristy experience you had?

We concluded our final day with a sunset cruise. Portland offers several options, but make sure to book ahead. We witnessed many eager tourists being turned away when they tried to purchase tickets right before departure. We opted for the Casco Bay Sunset and Lighthouse Cruise ($52/person) to take in Diamond Pass and the Calendar Islands, and we were glad we arrived early—securing fantastic seats on the upper deck. 

Where’s the best shopping spot?

In Maine’s charming Arts District, stop by Soleil, a gift shop where you’ll want to grab almost everything, especially if you’re the kind of traveler in search of a cute keychain (how about a dog in a sweater?), an adorable lobster toiletry bag, or a notebook adorned with a metallic croissant on the cover.

Cross the street to visit Loquat. It buzzes with creativity, as you can even see artists at work in the back. Stock up on shea butter or pick up a Shirt of the Week. If the vibrant colors inspire your artistic side, consider exploring the nearby galleries. The Portland Museum of Art is a must-see, and it's free on Fridays (otherwise, it’s $20 per adult). Keep an eye out for spaces showcasing student work from the Maine College of Art & Design as you wander around.

What must-have items did you bring?

Layering is key, along with comfy, grippy sneakers for walking on cobblestone streets and boarding a sailboat. Portland has a laid-back vibe. We noticed many people in sneakers and jeans, with a fair number sporting all black. I packed versatile jeans, a light sweater, and a linen chore jacket for layering, plus a baseball cap for unexpected rain. Accessories are great for elevating your look at nicer restaurants without being overly formal.

What additional tips do you have for someone planning a similar adventure?

• When to arrive: Allow yourself at least three days – we arrived Friday evening and departed late Monday afternoon, and we appreciated having time to relax between activities.
• How to get from the airport: For convenience, fly into the Portland International Jetport, located just 2 miles from downtown. From there, you can take a rideshare; our Uber cost $12 and took under 20 minutes. Alternatively, if you live within a few hours of Portland, consider taking the train; fares are reasonable, and you’ll enjoy views of foliage if you visit in the fall.
• Getting around town: Portland is easily walkable, especially if you choose accommodations close to the areas you want to explore. We focused on the West End and Old Port.