Friday
Evening
Target practice before waterfront dining

Moments before rush hour in Portland, I make my way down the cobblestone streets of the Old Port in search of a cup of coffee. I stop in at The Crooked Mile Cafe on the corner of Milk and Silver Streets and order an almond milk latte with a dash of vanilla and extra whip.

My accommodations for the night are at Pomegranate Inn, nestled in the West End. With vibrant color, lively artwork, and historic architecture, this 1900s bed-and-breakfast tells a story in every room. The worn, checkered floors and a tower of perfectly arranged sweets in the dining room remind me of my favorite fairy tale, Alice in Wonderland.

After indulging in freshly baked lavender cookies, I meet my mom at The Axe Pit to burn off some energy. This new South Portland business brings out your competitive side. Our instructor and axe-throwing expert, Paul, guides us through the proper technique before we let fly.

Resting on the Maine Wharf, Scales is best known for its seafood dishes and raw bar. We cozy into a seat with a seaside view and sip on a dry chenin blanc. The menu is filled with local favorites and flavorful descriptions. We start with a cup of creamy lobster chowder and smoky grilled octopus smothered in a chorizo-hazelnut vinaigrette. For our entrees we order pan-roasted halibut brushed with brown butter over fingerling potatoes and a dish of seared scallops with smoked bacon and maitake mushrooms finished with a rich, sweet potato cream sauce. We tap out after a decadent baked Alaska: a pumpkin cake topped with frozen coffee custard, spiced caramel, and toasted meringue.

Saturday
Morning
Breathe and refuel

We start the morning with a 90-minute vinyasa yoga class at Lila East End Yoga—a small, intimate space. We set our daily intentions and are encouraged to focus on our breathing while engaging in both challenging and restorative poses. Our instructor, Danielle, concludes the class with a beautiful serenade and lavender-scented eye pillows.

Breakfast is waiting for us when we return to the Pomegranate Inn. We refuel with mini quiches, fresh yogurt and granola, and toast slathered in hummus.

Afternoon
Thrift finds and street eats

Portland is well known for its unique and creative art and artisans, so we make a trip down Congress Street to visit Maine Craft Portland, a hub where local artists can showcase their work. Portland’s Arts District is also home to several consignment and vintage shops, including Find, Moody Lords, and Haberdashery Resale Clothing Co., which lace the streets with character, displaying retro jackets and antique jewelry. My favorite of the bunch is Material Objects, where I purchase a caramel-colored velvet jacket with a shearling-lined collar.

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We drive up Forest Avenue to Maiz, a hole-in-the-wall spot specializing in Colombian street food. My mom and I share a garlic grilled chicken arepa (a stuffed corn pocket) with a spicy Greek yogurt sauce, and cazuela de frijoles, a rice and bean bowl topped with caramelized plantains and crispy pork skin.

Evening
Luxury digs

At Dobrá Tea, just a stone’s throw away from tonight’s accommodations, we share a cup of Dhara white tea and a bowl of vegan sweet rice. Our cozy nook in the corner is a special place to unwind and recap our journey together.

I say goodbye to my mom and make my way to The Press Hotel. My room offers complimentary chocolates and a view of the city lights. It’s both cozy and luxurious. As I tour my palace for the night I can’t help but notice the wood-carved text on the walls and the hanging vintage typewriters. Previously the home of the Portland Press Herald, the hotel is made unique by its preserved architectural details and salvaged artifacts from the building’s time as a newspaper headquarters.

Before dinner, I make a quick stop at Lazzari, a stylish and low-key restaurant known for its wood-oven pizza and other Italian fare, and order the Moral Support cocktail, made with cucumber gin, mescal, Green Chartreuse, lime, butterfly pea flower, and pine bitters. It’s a perfect balance between smoky and refreshing.

After finishing my cocktail, I head to BaoBao Dumpling House, accompanied by my foodie friend Kyle. We order an array of dumplings, our favorite being the pan-fried and melt-in-your-mouth kung pao chicken.

We end our night in the Old Port with an espresso martini and a slice of vanilla cheesecake drenched in raspberry sauce from The Bar of Chocolate.

Sunday
Morning
Coffee on the beach and brunch

A late rise calls for brunch and scenic drives. As I make my way to East End Beach I stop at Forage, a bakery and cafe with celebrated wood-fired bagels. The breakfast sandwiches are in high demand, so I opt for an easy cup of coffee and continue on my way. At East End Beach I find the perfect rock on which to perch and people-watch for the next half-hour. Boats bob over calm waves, and the soothing breeze and faint chatter make it easy to lose track of time.

I return to the West End for brunch at Hot Suppa. With one of the best brunches in Portland, it’s no surprise there’s a line. The diner occupies an 1860 Victorian building with vibrant colors and brick walls inside. I’m told the brie and prosciutto egg sandwich is the day’s best seller, so without hesitation I order the last meal on my journey through Portland.