Just two hours from Boston and a quick 30-minute drive from Portland, Kennebunkport is the perfect destination for a day trip if you’re exploring southern Maine. This charming coastal town, known for its picturesque scenery and historic New England vibes, offers a diverse mix of relaxation and adventure. Whether you’re wandering through quaint shops, indulging in fresh seafood, or soaking up ocean views, Kennebunkport will make for an unforgettable day.
Let’s dive into how to spend a perfect day in Kennebunkport!
Getting Around: Walk or Bike
Kennebunkport is a very walkable town, but if you want to cover a bit more ground, consider renting a bike for a few hours. There are a couple of bike rental options:
Half day bike rental (4 hours): $29/adult
Full day rental (24 hours): $39/adult
Half-day bike rental (4 hours): $34/adult
Full day bike rental (24 hours): $42/adult
Morning: Explore and Kayak
Start your day with a walk or bike ride along the Kennebunk River. Dock Square is the heart of Kennebunkport, filled with boutiques and local shops that offer everything from coastal decor to jewelry. Grab a coffee from Dock Square Coffee House and explore the town. Be sure to stop at my favorite shops, 173 Mercantile and Bliss.
Kennebunkport offers a wide range of water activities, but I recommend renting a kayak for a unique perspective of the area. It’s a peaceful and serene way to explore the town, and the views from the water are truly breathtaking.
If you plan on renting a kayak or paddle board, consider renting from Kayak Excursions. Half day kayak rental starts at $50 and a full day kayak rental starts at $70.
Afternoon: Lunch, Beach and Cocktails
After exploring the town, head to The Clam Shack, a Kennebunkport staple known for its fresh, no-frills seafood. Whether you opt for their famous lobster roll or a basket of fried clams, you’ll experience a taste of Maine.
If you’re looking for something a bit more upscale, consider The Boathouse. Situated on the Kennebunk River, you can take in the views of the boats drifting by, while having anything from shrimp tacos to oysters. The nautical vibe and fresh seafood make it an ideal spot for a relaxing lunch.
No trip to Kennebunkport is complete without a visit to the beach. Head over to Goose Rocks Beach. This beach has a sandy stretch that’s perfect for lounging or taking a walk along the shore. There is also a small area at one end of the beach where you can enjoy the rocky, rugged coastline.
If you’re in the mood for a scenic drive, take Ocean Avenue. This route winds along the coastline, offering views of the Atlantic Ocean and the Bush family compound. You’ll have to stop at Walker’s Point for a photo-op- it’s one of the most picturesque spots in town.
After the beach or drive, go to The Spirit of Massachusetts for an afternoon cocktail. This bar is located on a historic schooner, making it the most unique bar in Kennebunkport. Try the Sea Cucumber, a refreshing gin drink or choose another from their Specialty Cocktail menu as you take in Kennebunkport’s waterfront views.
Evening: Dinner and Drinks
There are plenty of restaurants in Kennebunkport, but I recommend Chez Rosa or Luca, The Lost Fire’s patio.
Chez Rosa is a charming French restaurant in town and one of my favorite spots. The atmosphere is enchanting, with greenery draped across the walls and ceiling, French bistro chairs, and white marble tabletops. Their menu features classic French dishes with a modern twist. I recommend ordering the oysters, steak frites, and creme brulee. Pair your dinner with a glass of French wine, and you’ll have an unforgettable dining experience.
Luca, the bohemian patio at The Lost Fire, is just outside of town and is a must-visit for those who appreciate wood-fired grilling. The menu is centered around high-quality meats cooked over an open flame. The ambiance is magical, with twinkling lights strung along the trees, Adirondack chairs circling a fireplace, and drinks being served out of a small barn. The atmosphere is relaxed, making it a great spot for a memorable dinner.
Both of these restaurants in Kennebunkport offer something different, depending on what you’re craving and the atmosphere you’re in the mood for, but you can’t go wrong with either choice!
After dinner, head to Old Vines Wine Bar for a nightcap. This wine bar has a cozy ambiance perfect for unwinding and has an impressive selection of wines by the glass. It’s the idealt spot to enjoy your final drink in Kennebunkport.
Where to Stay: The Grand Hotel
For your hotel in Kennebunkport, I suggest booking a room at the Grand Hotel. Located in the heart of town, it’s just a few steps away from many restaurants and shops. The Grand Hotel offers a range of comfortable, newly updated rooms and amenities, such as complimentary bikes and kayaks, which make exploring the area easy. Guests even have the option to use the pool at the sister hotel, The Yachtsman. Also, a continental breakfast is included.
Whether you’re exploring for just a day or planning a longer stay, Kennebunkport’s charm, coastal landscapes, and delicious food will leave you wanting more.
Don’t miss my Ultimate Kennebunkport Travel Guide for a full breakdown of top activities, restaurants, bars, and places to stay.
Only staying for the weekend? Check out my How to Plan the Perfect Weekend in Kennebunkport post for a ready-made itinerary with top spots to see, dine, and relax!
