The charm and pace of Maine take the cake when it comes to late summer or early fall domestic travel. For our girls’ reunion trip, the goal was simple: maximize quality time and true relaxation. For us, that meant long walks, much-needed rest (especially for us moms of little ones), wine on the hotel lawn, and, when traveling with me, a food stop every 2–3 hours. For just a weekend, in my opinion, it’s the only way to pack in both the iconic and up-and-coming dining destinations.

Had we stayed one more day, I might have admitted that I overdid it on the lobster. But, truly, our Maine lobster picks were perfect — and yes, it’s just that good. We tried two different styles of lobster rolls at iconic haunts and cracked our own no-frills lobster dinner on the water after a private boat trip to an oyster farm. Then, for the grand finale — and I mean “grand” in every way — White Barn Inn’s four-course dining experience celebrated the hallmarks of New England with a refined, excellent preparation. A mini lobster roll with caviar and butter-poached lobster tail over gnocchi? Simply divine.

First things first, we stayed at Kennebunkport Captain’s Collection, a collection of luxury bed and breakfast-operated historic homes just a stone’s throw from town. The location is ideal, and the charm is unmatched. I highly recommend William Jefferds House for the aesthetic and sophisticated design. I fell in love with the common areas and patio. I highly recommend a late night by the fireplace with a bottle of wine from Maine & Vine (more on that below!).

We absolutely loved getting “lost” in the clusters of shops surrounding various good stops, hence why you’ll see me flag neighboring shops to our favorite restaurants. Scroll for the complete list, and be sure to tap through my Instagram story highlight for a visual version!

*Seacraft Vintage’s Kport Shops location*

SHOPPING

Kennebunkport Square

Daytrip Society: Precious gift store of trending accessories and tasteful nods to the region. I grabbed a lobster hair clip within seconds of entering and wore it all weekend!

Daytrip Jr.: Take all my money. A spin-off neighboring shop to Daytrip Society, this is he best children’s merchandising I have seen of Rylee & Cru and their family of brands, along with toys and more for little ones

Seacraft Vintage: Vintage-meets-contemporary quintessential New England style and goods in a precious navy cottage in town, with a second location (their original) right next to KPort Bagels

The Candy Man: Homemade old-school chocolatier and the trustworthy spot for touristy favorites, like chocolate-covered blueberries and lobster lollipops/gummies

Maine & Vine Wine Shop: Chilled bottles of rosé at the ready and a wall of Maine beers to bring home (if you check your bags!).

Northwest across the bridge in Kennebunk

Baske: High end interior and home decor shop that will make you want to restyle your shelves entirely

Bliss: Housed in the same building as Baske, a contemporary women’s clothing and accessories, including a great denim selection

KW Contemporary Art: The second-floor gallery above Baske and Bliss shops curates a fantastic contemporary-meets-coastal exhibition of visual artists, including Betsy Enzenberger (who sculps the melting popsicles I adore), Hunt Slonem, and Carolyn Johnson

Noble Goods: One-of-a-kind, artisanal small goods for the home

Southern Kennebunkport (with Mabel’s Lobster Claw)

Dannah for Men: Add 30 minutes to your trip to Mabel’s Lobster Claw to peruse this shop. Fabulous curation of men’s wear (Including great brands like Faherty), accessories, and gifts

Coveside Market: Adorable market with coffee stand, grab and go goods, local accoutrements, wines and chilled beers, and more takeaways for a perfect beach or boat day

DINING

Morning

Dock Square Coffee House: Begin your morning with a seasonal latte and blueberry crumb bar to fuel your town walk

KPort Bagel: New York style bagels and shmears

Fiafia Smoothie Cafe": Beautiful and bountiful acai bowls

Day

Clam Shack: Combo mayo-butter lobster roll box — but don’t miss the frozen blueberry margarita and blueberry hand pie

Mabel’s Lobster Claw: Lobster roll and a crisp Maine beer on the front porch

Cape Pier Chowder House: No-frills waterfront lobster “dinner”—or, in our case, a snack—and a clam chowder. We opted for a 1.5-lb. lobster and were very pleased with our selection.

Big Daddy Ice Cream: Taste the Maine blueberry pie for a unique flavor, or indulge in your classic favorite in a waffle cone

Night

Wandby Landing: Maine meets coastal Italian. Order the lobster agnolloti, crab toast, and pizzas

The Lost Fire: An outdoor oasis surrounding a fire pit. Splurge for the wagyu ribeye, sliced by your server, with shareable sides and Argentinian inspired starters such as the empanada of the day

White Barn Inn Restaurant: Worth the hype. A four-course seasonal menu, so phenomenal that I was paralyzed by the beauty between the choices – and I quickly realized I couldn’t make a bad one. The service, the wine menu, the cozy yet elegant candlelit barn ambiance make this experience memorable by all accounts. We saved this for the final night, which I recommend!