3 Days in Kennebunkport: A Charming New England Coastal Vacation

A perfectly paced three-day itinerary filled with lobster rolls, ocean views, charming shops, and just enough adventure

By Lori Stacy

I can’t quite believe it took me this long to get to coastal Maine. 

As a native Californian who now calls Texas home, I’ve spent years chasing coastlines like Big Sur, 30A, and the Carolinas, assuming I had a pretty good grasp on what “coastal charm” looks like. I’d never considered Maine.

But then I arrived in Kennebunkport, and immediately realized I had been missing an American treasure.

This isn’t a beach destination in the traditional sense. It’s quaint and undisturbed. Think salty air, weathered shingles, hydrangeas spilling over white fences, and what feels like understated elegance.

Here’s how to spend a perfect long weekend soaking it all in.

Day One

Check into the Kennebunkport Inn, exactly what you want in a New England getaway. It’s classic, charming, and perfectly located right in the heart of town.

You can walk everywhere, which is a huge part of the appeal. Mornings start with complimentary breakfast enjoyed inside or outside on the deck. The interiors here are cozy and coastal, with soft blues and nautical details.

Once you’ve settled in, start exploring. Begin with a walk through Dock Square, the heart of Kennebunkport. It’s easily walkable and features stores, galleries, and dining. You’ll want to begin your shopping here.

You’ll find beautiful, beach-inspired pieces at Beach Grass on Dock Square. Their coastal décor items will leave you longing for a place on the Maine coast.

Coastal Threads is a charming boutique with plenty to tempt you (I picked up a colorful tote, perfect to carry my shopping finds). Next door, Kate Nelligan is the eponymous store of Maine artist and designer Kate Nelligan, and her colorful art is on display. Pick up a set of plates or a pillow in one of her iconic designs as a reminder of your Maine vacation. The store also features unique coastal-inspired finds along with boutique clothing and jewelry.

Take in Maine art at downtown galleries including Abacus Gallery and Compliments Gallery. Can’t afford to take home a piece of art? Opt for the Abacus Calendar, featuring artwork by Maine-born artist Dana Heacock.

Lunch at The Clam Shack

If shopping has left you hungry, head over to The Clam Shack. This place is an institution, and it definitely lives up to the hype.

Located near the bridge, it’s more of a casual walk-up stand than a traditional restaurant. They serve what might be one of the best lobster rolls you’ll ever have. You choose: butter, mayo, or both. And yes, both is the correct answer. Don’t worry, the long line you will inevitably have to wait in moves quickly.

Continue Exploring

After lunch, head down Ocean Avenue. The mile-long stroll takes you along the water and is dotted with shops, hotels, and a few restaurants.

Pop into Dannah for elevated women’s wear and (yes) more coastal-inspired décor. And good news for the guys on the trip: nearby Dannah for Men offers casual menswear and goods in a relaxed, waterfront setting.

Continue down Ocean Avenue until you reach The Colony Hotel, a storied, traditional coastal inn. You get the sense as soon as you walk in that generations of families return here every summer. Pop in for a drink in the Marine Room. If it’s past 5 on Friday or Saturday, there might even be live music to accompany your ocean-view cocktail break.

For dinner, get a spot at The Boathouse. It’s perched over the Kennebunk River near Dock Square and is the perfect setting for a sunset dinner. Start with clam chowder (New England-style, of course) before moving on to the main dish. Whatever you choose, get a side of fries with their addictive Sriracha mayo.

For dessert, pop into Aunt Marie’s on your way back to the hotel and get an ice cream cone. Maple walnut is a good choice and very apropos.

Day Two: Boats, Lighthouses, and a Bit of History

Before breakfast and before the town truly wakes, take a quiet stroll to Dock Square Coffee House, just steps away from the inn. We grabbed lattes here one morning and were so glad we got there early as the line was out the door by the time we left. Grab your lattes and find a spot on the Mathew J. Lanigan Bridge to take in the view.

After breakfast, take your sweatshirts (yes, even in the summer) and get ready to explore the area via boat. A coastal cruise gives you a completely different perspective: rocky cliffs, lighthouses, and iconic New England homes perched right along the edge.

We booked with New England Eco Adventures, and it ended up being one of the highlights of the trip. We opted for a high-speed tour, and here is why: Tell your kids, “scenic boat tour” and they might roll their eyes. Tell them instead they’ll be going on a high-speed RIB boat that goes so fast they’ll have to hold on to their seats, and suddenly they’re first in line to get a spot on the boat. The boat skims along the coastline offering sweeping views of lighthouses and rocky islands. On a choppy day (ours was), it’s equal parts scenic tour and adrenaline rush. 

Ready for more lobster rolls? We were. So we headed to Mabel’s Lobster Claw, an institution since the 1950s. Sure, you can get burgers, but why would you?

After lunch, get the car and explore. First stop: Walker’s Point, the Bush family compound. You can’t go onto the property, but there’s parking and a viewing area at nearby Blowing Cave Park. It’s a quick stop, but worth seeing where generations of one of America’s most prominent political families has vacationed.

Spend the afternoon exploring more of town or head to Goose Rocks Beach. It’s softer and sandier than you might expect from Maine, a nice contrast to the rocky coastline.

On the way back, consider detouring to the Seashore Trolley Museum, where you can explore the history of this unique form of transport and even take a ride on a vintage trolley.

That evening, head toward the White Barn Inn, an Auberge property.

Before dinner, take a slight detour to the serene grounds of St. Anthony’s Monastery. The Monastery (and nearby Guest House, a nice option for affordable accommodations in Kennebunkport) are owned by Lithuanian Franciscan Friars who purchased the estate in the 1940s after escaping religious persecution in the Soviet Union. 

Then onto the White Barn Inn. Try to secure a reservation in the Barn (book early), but the more relaxed Little Barn next door is equally delicious.

Not quite ready to call it a night? Head to Ogunquit for a show at the Ogunquit Playhouse, a historic 1930s-era theater known for its Broadway-caliber productions and summer performances. It’s about a 20-minute drive and well worth it.

Day Three: More Adventure Before Departure

Don’t lollygag on your last day. After breakfast, pick up a kayak from Southern Maine Kayaks. They’ll guide you to the best spots to see salt marshes, quiet coves, and scenic stretches of coastline.

Grab lunch at Mornings in Paris, a cozy, casual spot known for its crêpes and sandwiches, with a laidback feel.

Afterward, explore the west side of town. Stop into Wooven for artisan goods from Southeast Asia. Next door, Whiskey Leatherworks will craft a custom belt on the spot. For colorful coastal wear, Pink Tangerine is full of Lilly Pulitzer and other bright, vacation-ready pieces.

Before heading out, grab a smoothie or light bite from Fiafia Café. It’s an easy stop before getting back on the road.

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Where to Stay in Kennebunkport

• Kennebunkport Inn: Classic, central, and walkable.
• Nonantum Resort: Family-friendly with waterfront views and a relaxed resort feel.
• The Colony Hotel: Historic and grand with sweeping ocean views.
• White Barn Inn: Refined luxury and one of the best dining experiences in town.
• Franciscan Guest House: A simple, budget-friendly option.
• The Boathouse Inn: Right on the water with easy access to Dock Square.

Where to Eat in Kennebunkport

If you’re staying for a few days, it’s worth branching out beyond the obvious spots. Kennebunkport has a surprisingly strong food scene for a town its size.

The Clam Shack
A must for your first lobster roll: simple and iconic.

Earth at Hidden Pond
A destination in itself. Seasonal, beautifully plated, and worth the splurge.

The White Barn Inn Restaurant
Elegant and refined. Your “big night out” meal.

The Boathouse Restaurant
Classic Maine views right on the water.

Mabel’s Lobster Claw
Rustic, no-frills, and exactly what you want.

Batson River Brewing & Distilling
Lively and modern, great for a casual night.

Rosella
A modern seafood spot with a contemporary feel.

Hurricane Restaurant
Upscale fare without being stuffy.

Fiafia Café
Smoothies and bowls, for when you just want a quick bite.

For Something Sweet

Aunt Marie’s
Old-school ice cream charm with classic flavors and generous scoops.

Rococo Artisan Ice Cream
Inventive flavors and absolutely worth the line.

Getting There

Fly into Boston (about a two-hour drive) or directly into Portland, just 30 minutes away. Boston typically offers better pricing; Portland wins on convenience.

What’s the Difference Between Kennebunk and Kennebunkport?

Kennebunk is more residential, with beautiful homes and beaches like Gooch’s and Mother’s Beach.

Kennebunkport is where the coastal-village charm lives, with Dock Square, the harbor, boutique shopping, and that quintessential New England feel. For a weekend trip, this is where you want to stay.

When to Visit Kennebunkport

Late spring through early fall is ideal, with peak season in July and August when the town is lively and in full bloom. September is a sweet spot, with fewer crowds, warm days, and crisp evenings. Fall brings beautiful foliage, while winter offers a completely different vibe and far fewer crowds.