Luxe Weekend Getaways: Portland, Maine


Portland, Maine is where you go to get away from big city life. Time slows down. The coastal air is fresher, cleaner, and brighter. The perfect blend of stylish and sophisticated, you can find something to do for everyone. One of the largest towns in Maine, Portland sits on the edge of Casco Bay, and the population is just under 70,000.


Portland Harbor Hotel is a classic in the heart of the Old Port district. After a quick taxi ride from the airport, everything you need is within walking distance from the AAA-Four Diamond property. The Old Port District is the perfect place to stay, with glamorous 19th-century architecture, galleries, shops, nightlife, breweries and restaurants.

The hotel itself has been renovated and has a quaint yet upscale cozy feel. Fireplaces in the lobby make for the perfect area to chill with a glass of wine, and the courtyard is not only a gorgeous view from the inside rooms, but a central meeting point for guests around the fire pit in the early evenings.

Each guestroom is outfitted with lustrous dark wood floors, local artwork and coastal colors, and several room options are available.


Portland is home to almost 400 different restaurants and ranks among the top cities in the US for restaurants and bars per capita. Portland was named “Foodiest Small Town in America” by Bon Apétit Magazine in 2009 and was named “Restaurant City of the Year” in 2018.

In Portland you can find microbreweries and brewpubs, the historic Portland Farmers Market (in existence since 1768), high-end restaurants, casual eats and everything in between. The food focal point is based on local, organic, farm to table and plant-based foods. Portland has also been noted as one of the most Vegan and Vegetarian-friendly cities in American.

Where to go?  

J`s Oyster is a family-owned eatery that has been opened since 1977, and is still run by the family heirs. Situated steps from the water, J’s is popular with locals and tourists alike, and conversations overheard at the bar span from who is dating who in town to best reductions for short ribs. This no-frills diner serves up local brews (like Allagash, Gritty’s Seasonal and Geary’s Seasonal) along with fresh local seafood. Not to miss: The Lobster Stew.

Blue Fin

A timeless upscale dining experience, Blue Fin has the ambiance of a swanky New England home, creating comfort chic with contemporary fireplaces, book stacks, rustic touches and muted, dark colors. Chef Tim Labonte is a Maine native, and the Maine staples are reflected in his menu; fresh lobster rolls, local bread, artisan cheeses, seasonal fruits and vegetables paired with classic cocktails and a pleasant wine list.

Hot Suppa is located in a Victorian building dating back to 1860, and you can’t miss it with the usual long lines outside. Known for their fresh ingredients, this happening brunch spot only has 10 tables and 5 bar seats, so come early (No reservations are accepted). Original recipes are made from scratch, inspired from a road trip by the owner brothers that took them across the US, sampling barbeque, drive-ins and more.

 The Holy Donut

A unique take on the classic donut, these tasty treats are made with mashed potatoes and local ingredients. Even though there is usually a line, it moves fast. Favorites include the cheddar bacon, cinnamon sugar and coconut.

Portland Hunt & Alpine Club

For a chic weekend cocktail, head to the Portland Hunt & Alpine Club on Market Street. An extensive cocktail list greets you, divided up into classics, refreshing, adventurous and wild card. Guests love the small bites, especially the popcorn with green Chile powder, butter and Parmesan, daily selection of deviled eggs and Smorgasbord.


Portland Museum of Art

Founded in 1882 as Portland Society of Art, The Portland Museum of Art is one of the only museums to be founded by artists themselves. The museum houses a significant collection of 19thand 20thcentury art from American and Europe, as well as highlighting Maine artists. Over 18,000 pieces can be found including Andy Warhol, Jasper Johns, Monet and Pierre-Auguste Renoir.  

Different structures make up the museum, including an 1801 Federal-Style Mansion, 1911 Beaux-arts style building and a modern building designed by Henry Nicolas Cobb, which opened in 1983.

Sweetgrass Winery & Distillery is a local distillery serving up homemade gin, hard apple cider, rum, apple brandy, vermouth, whiskey, wines and bitters made from Maine-grown fruits and grains. For only $5, try a flight of your choosing.

The Arts District located on Congress Street is the perfect place to spend the afternoon wandering. Home to the Portland Museum of Art, Portland Stage Company, Maine College of Art, Maine Historical Society and many other small galleries.


Dean’s Chocolate Shop

Bring back a sweet treat of artisan chocolates from Dean’s. These small batch chocolates use organic maple tapped from Madison, Maine, salt from the coastal Marshfield region and butter from Kate’s Homemade in Old Orchard Beach. Over 30 decadent varieties are available including truffles, caramels, buttercreams and chocolates.


Stop by family-owned Skordo (Greek for Garlic), and check out cooking inspiration for the whole family. From boutique spices and herbs, cookbooks, specialty kitchen tools, recipe kits and delicate glassware, the unique, beautiful items will inspire you to spend some time in the kitchen.

Peyote Moon

A sustainable fashion store located on Exchange Street, Peyote Moon supports artisans, small businesses and the slow fashion. Each carefully curated piece is made to be kept year after year, and is high quality, durable and timeless. Brands include Mara Hoffman, Micaela Greg and The Wild Unknown.

Kimberly Fisher

Kimberly Fisher is a Freelance Writer and On-Camera Host based in New York City. Kimberly's work has appeared in over 45 publications including Huffington Post, JustLuxe, Luxe Beat Magazine, Luxury Lifestyle Magazine, Ocean View Magazine, Pursuitist, Sherman's Travel, Sunset Magazine,, and USAToday. Her travels have taken her to sip champagne cliffside in Portofino, shark feedi...(Read More)

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