By Jamie Edwards, award-winning travel writer who’s visited 70+ countries on all 7 continents
There’s something about a small city with a big soul. And wow, does Portland, Maine, have soul to spare. And lobsters to spare… but I’ll get to that later. With salty sea breezes along the wharf, where the city’s maritime vibe comes to life, and a dining scene anchored in seafood, Portland has become one of my favorite summer weekend getaways. I mean, where else can a grown woman eat a world-class meal wearing a bib? Portland, you’re my kind of town.
The wharves and docks in Portland aren’t just scenic backdrops—they’re living, working places that hum with history. Weathered wooden piers jut into Casco Bay where lobstermen haul traps at dawn. Stacks of colorful buoys are waiting to be tossed into the sea. Seagulls swoop and whoop overhead, fishing boats bob in the harbor, and there’s always the faint scent of salt and diesel in the air.
Ready to spend an unforgettable summer weekend in Portland, Maine? Let’s go!
A Waterfront City That Shines in Summer
So, what to do in Portland, Maine? This waterfront city is known for many things: lobsters, lighthouses, and lantern-lit piers among them. And while Portland shines year-round, summer is when it really thrives. The harbor bustles with working boats, outdoor patios brim with locals sipping cocktails under fairy lights, and the weather is, in a word, divine.
Expect summer highs in the 70s and 80s, with cool mornings and nights. In the summer, the sun lingers well into the evening, so there’s no reason not to stroll along the pier and indulge in a post-dinner scoop of mint chocolate chip.
Historically, Portland’s waterfront was the beating heart of the city’s economy. A hub for shipping, fishing, and later, railroads. Portland built its fortune on the back of the Atlantic Ocean and the humble lobster. The city’s crustacean obsession isn’t a tourist trap—it’s an institution. Lobster boats still chug into the harbor each morning, and what they haul in ends up on your plate by dinner. That’s worth a summer weekend in Portland, Maine, in and of itself.
Portland Always Accommodates
Portland has accommodations to suit all budgets, travel styles, and needs. But the Press Hotel is a noteworthy standout. Housed in a former newspaper building, this 110-room hotel in the Old Port District brilliantly honors the traditional craft of typesetting and old-school journalism. Clunky, black typewriters and letterpress wood blocks are treated as modern art. Your kids won’t believe these relics were the precursors to Apple and Dell.
The Longfellow Hotel is one of Portland’s newer boutique hotels. An SLH property located in the historic West End, it’s refined without being pretentious (despite its plush mattresses and down comforters). Don’t miss Five of Clubs, their lobby cocktail bar, for a plate of oysters or caviar service. The Longfellow may be a bit further away from the urban buzz, but guests are welcome to take advantage of a complimentary luxury car service to take them downtown. A cushy hotel perk, indeed!
If you’re looking for a place that feels like staying with your most fabulous friend—the one who you go to for fashion recs and advice—try The Blind Tiger Guest House. Blind Tiger puts you in the heart of the city with locations on both Carleton and Danforth Streets. Think B&B meets private club, with hip art and one-of-a-kind furnishings that ooze style. Grab your fabulous friend and spend a summer weekend in Portland, that you’ll both remember.
Portland’s Waterfront, A Weekend Must
There’s no better way to start your Portland weekend adventure than by heading to the waterfront. Commercial Street is the city’s nautical backbone. Watch fishing boats unload their daily catch and embrace the harbor air. It’s filled with the kind of energy that’s quintessentially Maine.
Portland’s shopping scene is compact but curated. Independent stores showcase everything from handmade jewelry and housewares to vinyl records and vintage jeans. Wander cobbled Exchange Street, where the boutiques and galleries will make you want to redecorate your home in navy blue and white. You may not need a sea salt candle or a ceramic coaster—but I’ll bet you a 3 pound lobster you’ll end up taking them home (along with lobster-patterned socks, lobster salt and pepper shakers, and lobster trivets). The lobster craze is no joke. Be warned.
Drift towards Middle Street, where high-end fashion and local art live side by side. Then tackle Congress Street, where things get a little off-beat. Here you’ll find used bookstores, vintage records, and eccentric boutiques.
Some other Portland favorites? Ember is on the outskirts of town but a must-visit for beautifully designed home goods and handmade ceramics from the husband and wife team behind Campfire Pottery. The Sea Bags Flagship store, on Commercial Street, is a visual delight. Its bold and colorful totes are made from recycled sails. No two are exactly alike.
For kitchen gadget lovers like me, Le Roux is a dangerous stop. Sample a few of their flavorful olive oils and vinegars. I don’t even cook, and walked out with four bottles. Browne Trading Company deserves a mention, too. It’s part gourmet shop and part seafood market, so if you’re looking to bring a taste of Maine home, this is the place to visit.
Dining In Portland Isn’t Only About Lobster (But It Can Be)
One weekend in Portland is enough to fall in love with the food scene, but not nearly enough to eat your way through it. That said, book a table at Fore Street, one of the city’s finest dining spots. It’s a place where the ingredients are local and the open kitchen buzzes with activity. The bread is insanely good, and the mussels are a must. Fore Street hits all the marks for a fabulous dining experience in Portland.
For something more playful, Crown Jewel on Great Diamond Island has the summer vibe nailed. Take a scenic 30-minute ferry ride (or even shorter water taxi ride) to Crown Jewel. It’s bright and breezy, with tropical energy, fresh oysters, and lobster tails. The theme is decidedly flamingo pink. So order a sparkling rosé to go with that lobster tail and enjoy a Portland island escape.
Interested in something more casual? Head to Duckfat, most famous for its crispy Belgian fries cooked in (you guessed it) duck fat. According to the website, ‘Duckfat has been serving cones of hot, golden, crispy duck fat-fried Belgian frites in downtown Portland, Maine since 2005.’ Duckfat, you had me at golden. Tiny, unpretentious, and utterly addictive, don’t leave without ordering a famous milkshake to go with those fries. As I always say, vacation calories don’t count.
Union, at The Press Hotel, is an elevated, elegant restaurant rooted in local flavors. It’s refined without being fussy, and showcases Maine’s best ingredients. Highlights include “Chicken Fried” Sole with asparagus and rhubarb velouté, and Maine Lobster Bucatini with chicory, local pasta, and green garlic. The honey they use is harvested from their rooftop. Rooftop honey? You can’t get more locally sourced than that.
In the mood for oysters? Eventide Oyster Co. is a modern revival of the great American oyster bar. It serves impeccably fresh shellfish and reimagined takes on classic New England fare—thanks in part to its enviable proximity to the Gulf of Maine. Expect an expertly curated wine list designed to complement the briny flavors, craft cocktails with character, and coastal indulgence done right in the heart of Portland’s Old Port.
Lobstah, Lobstah
Let’s spend a little more time on lobster, shall we? This is Maine, after all—where crustacean is king and melted butter flows like wine. If you visit Portland and don’t indulge in a lobster roll, were you even there?
At The Highroller Lobster Co., the lobster is fresh off the boat, and the options go gloriously off-script. Aside from traditional rolls, try a Lobster grilled cheese or a lobster taco. Choose your own sauce—like charred pineapple mayo or jalapeño lime butter. Highroller is hip and unapologetically loud, so be prepared.
Bite Into Maine is less a restaurant and more of a pilgrimage. One of their many food trucks is parked at Fort Williams Park, a scenic bluff overlooking the ocean and the iconic Portland Head Light. Sit on a bench, lobster roll in hand, seagulls circling, and ponder the reasons why you don’t live in Maine.
Their rolls come in six styles, from buttery Connecticut to herby picnic-style, and if you can’t decide, you’re not alone. Order two and call it ‘research.’ There’s something about the lighthouse setting and ocean air that makes these lobster rolls taste better.
Remember, you didn’t come to Portland for the salads. Portland lobster is the undisputed main event. Whether piled high on a toasted split bun or layered into a gooey grilled cheese, it’s a rite of passage—and totally worth the buttery mess.
On the off chance you’ve had your fill of lobster, Mr. Tuna will satisfy any other seafood cravings, especially the tuna-related ones. What was once a humble food truck in Portland is now a full-service restaurant serving all things toro. According to The New York Times, the ‘Tuna de Tigre’ is one of their best bites. This delectable combo of diced tuna, coconut, avocado, fresh cilantro, red onion, and crispy shallots have helped this seafood haven earn multiple culinary awards. But yes, they also have lobster.
Summer Weekend Nights in Portland, Maine
Portland nightlife is completely on trend. At The Portland Hunt + Alpine Club, the cocktails are as thoughtful as the Scandinavian-inspired interior. With intriguing names like Pepper Smash, Remember the Maine, and the Vacation Old-Fashioned, you may need to stay a bit longer for more ‘research.’
Papi is a lively Latin restaurant and bar with a magnetic aura. The Beverage Director’s Puerto Rican influences light fire to the cocktail menu with standouts like the Lost My Mojo Martini and the Boriken Gold. It’s fun, energetic, and the kind of place where the second round comes before you realize you’ve finished the first.
If you want to end the night with something a little quirky, pop into Room for Improvement. This brick-faced bar on Wharf Street is known for playful updates on classic cocktails. Add a shot of Portland eccentricity and a low-key menu that will have you settling in for the night.
Portland, Maine Attractions Worth Highlighting
No visit to Portland is complete without a trip to Fort Williams Park, home of the picture-postcard Portland Head Light. Even if you think you’ve seen enough lighthouses in your lifetime, this one will impress you. Perched on dramatic cliffs with the ocean crashing against the rocks behind it, there’s perhaps no better Instagrammable lighthouse in the country. Don’t forget to leave room for a lobster roll from the Bite Into Maine food truck while there.
Back in town, make time for the Portland Museum of Art. It’s small and thoughtfully curated. You’ll find a mix of American masters (like Winslow Homer and Andrew Wyeth), European pieces, and contemporary exhibitions. The space is airy and beautifully lit. If you’ve been out in the hot sun all day, the air conditioning alone might be a reason to pop in. And since it’s located in the Arts District, you can also explore galleries, shops (Ember is around the corner), and cafés nearby.
Portland Has Soul To Spare
What starts as a simple summer weekend in Portland becomes a series of colorful picture-postcard moments (or, dare I say, Instagrammable ones): lobster rolls with a lighthouse view, bespoke cocktails with a backstory, flamingo-themed restaurants, and harbor vistas that stop you in your tracks. Portland’s soul can be found behind old-weathered shingles and inside red-brick cocktail bars. It can be found on its cobbled streets and in mural-filled back alleys. Even when you’re not looking for a little soul, you’ll no doubt stumble into it.
Portland, Maine has soul to spare. And lobsters to spare… in case I didn’t already make that clear.
Want more Maine? Check out our tips for The Perfect Summer Weekend in Kennebunkport, Maine. (And a winter visit to Kennebunkport ain’t too shabby either!)
Jamie Edwards is an avid traveler, travel writer, and photographer. After 25 years of living and traveling around the globe, she launched I am Lost and Found, her adventure/luxury travel website. Jamie’s goal is simple: to inspire travel.
CIRE Travel is a full-service travel agency headquartered in New York, NY. Our expert corporate travel planners, honeymoon travel agents, and luxury travel planners support clients across the country and around the world.
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