Copy My Trip: 3 days in Portland, Maine

Lonely Planet’s senior social media manager, Rachel Lewis, recently returned from a weekend with her wife in Portland, Maine. Here she shares her trip highlights and what to prepare for before you go.

I’ve always had a clear picture in my head of what visiting Portland, Maine would be like, and, honestly, it was pretty stereotypical: buttery lobster, stripes and linen, setting sail from the Old Port and thumbing through pottery at local shops. I’d never been to Maine, period, but when I told my grandmother (who’s from Massachusetts) that I was planning a long-weekend trip with my wife, she had two recommendations: eat as much as you can manage, and go to the locally owned Cool As A Moose (and buy her a mug for Christmas – on it, Gramma). My wife and I landed with empty tums and space in our luggage for goodies, and hit it.

I want to help you do the same. Here are a few things that made my weekend in Portland so memorable.

Where did you stay? What was the vibe?

The Longfellow Hotel in the West End is a newly opened boutique hotel with a heart for sustainability. On our first morning in Portland, we tested out room service with a breakfast order of an iced oat milk latte. I got just what I was craving, and my wife couldn’t stop raving over her breakfast sandwich – baked egg, spicy mayo and pepper jack on an English muffin.

I was particularly impressed with the creative mocktail menu at its dinner and drinks venue, Five of Clubs. Finding good alcohol-free drinks when traveling sober (or sober curious, in my case) can be tricky, but the “functional cocktails” are stunning. I had a Rosarium – bitter orange, earl grey, pomegranate – and a Vacationland Refresher – wild Maine blueberry, cardamom, lemon soda. The earl grey was a great intro to the -ber months.

The spa, Astraea, has an infrared sauna (reserve it in advance!), and you can get your very own space with a bathroom, rain shower and sauna. There are a few different massage options. We chose Mindful Dreams, a meditative, rhythmic full body massage ($145/person for 60 minutes). Sip peppermint tea and feel wonderful as you lounge about in your new skin (okay, I know that’s not how it works, but it’s how it feels).

What was the best thing you ate or drank?

I'm not even going to attempt to single out a "best" meal in Portland, but with its foodie reputation, you can expect to dine well. These are the dishes, snacks and flavors that stood out for us.

Brickyard Hollow Brewing Company is a local chain that makes gourmet pizza from Freeport to Yarmouth (the original) and beyond. We went with cheese pizza, and it was beautiful in its simplicity: 12 inches of cheesy goodness with an olive oil base. Next time, though, I’d grab something more experimental, like its blueberry pizza with Maine blueberries, rosemary ricotta, roasted shallots and lemon zest.

Green Elephant, a vegetarian bistro, does not take reservations, so get there at 11:30am when it opens for lunch. Grab yourself some deep-fried vegetarian spring rolls and king oyster mushroom tempura. If you’re a vegetarian like me, you’ll appreciate a space where you can eat literally anything without having to triple-check that the allegedly vegetarian pseudo-meat you’re taking a bite of is 100% not meat. Go for the ginger noodles and appreciate the spice (make it vegan by skipping the egg).

Another tasty lunch option includes Benkay, a Japanese restaurant and sushi bar. Consider the teriyaki tofu; it’s fast, hot and surrounded by colorful veggies. For a filling dinner, we hit Black Cow, a burger joint. I got a veggie burger with a mushroom lentil patty, iceberg, pickled red onion, radish and black garlic mayonnaise on its signature black cow bun.

When you need a break during your Portland wanders, grab a donut at Holy Donut (consider the blueberry glaze). Navis Café on Thames Street – about a block from the water – serves great egg-white bagels and iced decaf vanilla lattes for breakfast on the move.

What was the most touristy thing you did?

We wrapped up our final day by hopping on a sunset cruise. Portland has quite a few options, but no matter what you pick, book in advance. We saw many excited tourists get turned away when they tried to buy tickets just before sailing. We chose the Casco Bay Sunset and Lighthouse Cruise ($52/person) to see Diamond Pass and the Calendar Islands and were glad we arrived early – we snagged stellar seats on the upper deck.

Where is the best place to shop?

In Maine’s historic Arts District, swing by Soleil, a gift shop where you’ll want pretty much everything, especially if you’re the sort of traveler who wishes they had a cuter key chain (how about a dog wearing a sweater?), an adorable lobster toiletry bag or a notebook with a metallic croissant on the cover.

Cross the street and make your way to Loquat. It’s alive with design, literally, considering that you can see artists working in the back. Stock up on shea butter or grab a Shirt of the Week. If all this color makes your artsy heart grow three sizes, consider swinging by any of the galleries along the way or nearby. The Portland Museum of Art is the obvious choice, and it’s free on Fridays (otherwise it’s $20 per adult). You’re almost certainly going to run into spaces showcasing student work from the Maine College of Art & Design, so keep your eyes peeled as you stroll.

What essential items did you pack?

The name of the game is layers and comfy, grippy sneakers for lots of strolls on cobblestone streets and stepping onto a sailboat. Portland is pretty chill. We saw loads of people in sneakers and jeans, and quite a few people in all black. I packed a pair of jeans that could be dressed up or down, a light sweater and a linen chore jacket for layering, and a baseball cap in case of rain. Accessories are handy for nicer restaurants where you want to feel like you dressed up without dressing up.

What other tips do you have for someone planning a similar trip?

• When to arrive: Give yourself at least three days – we arrived Friday evening and left late Monday afternoon, and were glad we had time to laze about in between activities.

• How to get from the airport: For ease, fly into the Portland International Jetport, just 2 miles from downtown Portland. From there, hop in a rideshare. Our Uber was $12 and took less than 20 minutes. Or, if you live within a few hours of Portland, consider taking the train; prices are reasonable, and bonus: you can get in views of foliage if you come during fall.

• Getting around town: Portland is walkable as long as you choose accomodations near the hub where you want to explore. We zeroed in on the West End and Old Port.