If there’s one aesthetic that seems made for summer, it’s “coastal granddaughter.” Think linen button-ups tossed over swimsuits, sun-warmed lobster rolls eaten dockside, tote bags filled with boutique finds, and long evenings spent dancing with your best friends before heading home to a cozy seaside town. And nowhere is better for perfectly capturing this vibe than Maine.
When two of my friends and I packed up for a long weekend trip to visit our fourth friend, who currently lives in Maine, that’s exactly the energy we were chasing. We wanted four days of everything Maine has to offer. I’m talking small-town charm, beach walks, fresh seafood, and a night out in Portland’s bar scene. Having a local as our guide helped us uncover spots we might have otherwise missed.
Here’s everything we did on our weekend trip, day by day.
Day one: settling into Kennebunkport
The first day was a shorter one, mainly focused on getting settled in. Our first stop after the long drive into southern Maine was Arundel Wharf Restaurant. The nautical vibes and waterfront setting instantly made it feel like we’d stepped into a postcard. I went classic with fish and chips, which were crisp, golden, and generously portioned. Eating seafood this fresh, right by the water, feels like a rite of passage in Maine.
Naturally, dessert came next. Big Daddy’s Ice Cream is a local favorite. We couldn’t resist the s’mores flavor, a creamy, chocolatey blend complete with graham cracker crunch. It was pure summer nostalgia in a cup. The prices may seem a little steep at first but trust me when I say you get more than what you pay for. The name says it all.
The night ended at Garden Street Bowl, a mix of bowling alley, arcade, and bar. We ordered a flatbread pizza and fried Brussels sprouts, which were both absolutely delicious. It was a very cozy space with great staff, great food, and a ton of fun. It was the perfect lowkey first night to ease into the trip, and now I have a strip of goofy pictures from the photo booth to show for it.
Day two: shops, beaches, and Portland nightlife
Saturday was our most packed day. It captured the balance of cozy, cottagecore small-town Maine with the bigger city nightlife in Portland.
We started in downtown Kennebunkport at Mornings in Paris, a charming café that feels straight out of a European side street. Pastries and macarons filled the display cases, but we were there for the crepes.
I ordered the Blue Lemon Cheesecake Crepe, filled with lemon cream cheese and Maine blueberries and topped with graham cracker crumbs. It sounded dreamy but unfortunately fell a little flat since mine had barely any filling. My friends lucked out with their Nutella Fruit Crepes. Stuffed with strawberries and bananas, they did not have the same issue.
To drink, I had the Campfire Cold Brew, a decadent mix of cold brew with dark chocolate sauce, toasted marshmallow, cold foam, and graham cracker crumbs. It was hands-down delicious and easily the highlight of my stop there. If you go, I’d definitely recommend the drinks and pastries, and maybe stealing a bite of a friend’s Nutella crepe if you can.
From there, we hopped between adorable shops. Daytrip Society had posters and knickknacks that screamed coastal New England charm. Whimsy Shop lived up to its name with whimsical prints and homey touches. At Lobstore, we picked up unique stickers from a randomized sticker dispenser, and Saxony Imports was where I grabbed my go-to travel souvenirs: a shot glass and postcards.
By mid-afternoon we were ready for food and drinks, so we made our way to Pilot House. This boat-bar hybrid was peak Maine vibes. We ordered fried bites like coconut shrimp and haddock alongside our Aperol spritzes and piña coladas. We sat outside, sipping, laughing, and taking pictures, the exact kind of moment that makes a girls’ trip so memorable.
Later, we wandered to the beach. The air was brisk since we went around 5 p.m., but it turned into one of the trip’s most unexpectedly perfect stops. We sat in the sand playing some summertime classics on our speaker, chatting and petting dogs that came running over to us as their owners strolled the shoreline for their pets’ daily evening walks. It was calm and grounding, a reminder that you don’t always need to fill every hour with something “big.”
Dinner was at the iconic Clam Shack, where I had a $36 lobster roll. Pricey, yes, but honestly worth it. It was buttery and perfectly tender. It felt like a requirement to have one at least once during this trip, and I savored every bite.
The Clam Shack partnered with Aunt Marie’s, a cute little ice cream shop a short walk away, to provide a buy-one-get-one ice cream deal to their customers. So, for dessert, we made our way over and went classic with s’mores again (a flavor trend of the weekend).
That night, we drove half an hour into Portland to check out the nightlife. Amigos was our first stop, a lively bar with Jell-O shots and a live band. Then we headed to Oasis, a club with an upstairs dance floor, an outdoor patio, and one of the best DJs of the trip.
Cheese Louise, a local favorite, satiated our post-bar cravings. This late-night spot was perfect, as it was open until 2 a.m. and provided all the carbs we needed. Cheese Louise takes the comfort food classic to another level with melty, over-the-top combinations. It was the perfect way to end a night out.
Day three: breakfast, mini golf, and another Portland night
Sunday kicked off with a hearty breakfast at Mike’s All Day Breakfast. I went for a western omelet while my friends grabbed breakfast sandwiches. The service was slow, but the food was good. It was the kind of casual, slightly understaffed diner that adds to the authenticity of traveling through smaller towns.
Afterwards, we wandered through an artisan craft fair. We picked up charming bookmarks, stickers, and art as souvenirs before heading to Raptor Falls Mini Golf. The course is dotted with animatronic dinosaurs, making it both kitschy and genuinely fun.
It’s not something you’d typically classify as “coastal granddaughter.” But honestly, that balance between aesthetic Instagram moments and goofy fun made for some unforgettable memories.
Next we stopped at Rococo, a dessert bar that specializes in making innovative desserts and craft cocktails. I split the chocolate chip cookie royale with a friend, which had a quirky flavor combination that worked surprisingly well.
For $16, you get a chocolate chunk cookie and salty sweet cream ice cream topped with sea salt caramel, black tahini whipped cream, and sesame brittle. It was a little small for the price, but absolutely delicious and totally worth trying. They also had plenty of unique takes on milkshakes, ice cream flavors, affogatos, espresso martinis, and plenty of other dessert and cocktail classics.
That evening, we made the drive back into Portland for a more upscale dinner. At Via Vecchia, Aperol spritzes were practically the table’s uniform order. I split the meatballs (some of the best I’ve ever had) with a friend, and the warm focaccia disappeared quickly. Another friend’s campanelle pasta was equally delicious.
Pro tip: make a reservation here a couple of days in advance. We lucked out with a short wait as walk-ins and ended up with a fantastic table overlooking the bar area, but a seat wasn’t guaranteed.
While waiting for our table, we grabbed drinks at Wharf Street Yacht Club. This small bar had super friendly staff and a chill vibe. I split a perfectly balanced cosmo with one of my friends, the ideal pre-dinner cocktail.
We ended the night barhopping along Portland’s Wharf Street. Bonfire Country Bar leaned fully into its theme with saddle seats and nonstop country music. It wasn’t our usual scene, but it was undeniably fun and packed with people. We circled back to Oasis, because we had enjoyed ourselves so much the night before, and the whole strip proved Portland’s reputation as a great city for nightlife.
Day four: a cozy send-off
On our last morning, we ended the trip at Bev’s Café and Market in Kennebunk. The café immediately stood out for its welcoming energy, a refreshing and comforting way to close out the weekend.
I ordered a caramel iced coffee and a cherry-peach galette-style pastry that was out of this world, though the display case was also full of s’mores cookies and cinnamon buns. We lingered over coffee and pastries, not wanting to rush into our goodbyes.
Final thoughts: why Maine delivers the coastal granddaughter dream
Leaving Maine, I felt like I finally understood why this state has such a hold on summer culture. The “coastal granddaughter” aesthetic isn’t just a TikTok trend. It’s a lived experience when you’re here. It’s the salt air in your hair, the understated but chic shops, the lobster rolls eaten on docks, and the way nights can shift from sipping spritzes to dancing under the lights.
Traveling with friends in your early 20s, on a moderate budget but still wanting those memorable moments, felt like the perfect way to approach Maine. Sure, we splurged on Maine classics like lobster rolls, Aperol spritzes, and Via Vecchia. But we also embraced spontaneous, low-key fun with beach walks, craft fairs, and mini golf.
The key to the perfect getaway? Let yourself enjoy both the iconic “coastal granddaughter” moments and the quirky, unexpected adventures that make a trip memorable.
If you’re planning your own trip, my best advice is this: balance the aesthetic with the unexpected. Go to the Clam Shack or the fancy Italian restaurant, yes, but also let yourself end up at a dino-themed mini golf course or at a beach full of dogs. Maine is at its best when you let it be both timeless and fun, just like the friendships you bring along.
