A Perfect 3-Day Itinerary for Kennebunkport, Maine
Kennebunkport, Maine, is one of those postcard-perfect coastal towns that offers the best of New England charm. Whether you’re visiting for the first time or returning to uncover more of its hidden gems, a 3-day trip to Kennebunkport delivers the ideal mix of relaxation, outdoor adventure, and local culture. With its scenic harbor, quaint streets, and mouthwatering seafood, you’ll quickly see why this iconic Maine destination is so beloved.
Here’s a 3-day itinerary to help you experience the best of Kennebunkport!
Where to Stay
The Colony Hotel
Our stay at the Colony Hotel was unforgettable! Nestled along the stunning Goose Rocks Beach, this historic hotel offers sweeping views of the Atlantic Ocean and some of the most beautiful coastline in the area. Perched on a hill, the hotel provides a peaceful, scenic setting that feels worlds away from the hustle and bustle, yet is just a short drive to Kennebunkport’s lively Dock Square.
Whether you’re relaxing on the spacious veranda, lounging by the outdoor pool, or strolling down to the beach (with private access, no less!), the sounds of the ocean are never far away. Also, the hotel’s location also makes it a perfect base for exploring the surrounding area, from boutique shops to art galleries and seafood spots in the heart of the town.
The first time we visited Kennebunkport, we stayed in an Airbnb, which we loved, but during that trip, we popped by The Colony for drinks. The breathtaking oceanfront views won us over, and we knew we had to splurge and stay here next time!
Other popular places to stay:
When to Go
The best time to visit Kennebunkport is undoubtedly during the summer months (June to August), when the weather is warm and the town is alive with activity. However, Fall (late September to early October) offers a quieter atmosphere and stunning foliage, making it a fantastic time to visit if you want to avoid the crowds. If you’re after great deals and fewer tourists, consider coming in the spring or early fall.
Pro Tip: Even in the summer, Maine weather can be unpredictable—think cool, breezy mornings and the occasional rain shower. Be sure to pack an umbrella and a cozy sweatshirt!
Day 1: Explore the Heart of Kennebunkport
Morning: Stroll Through Dock Square
Start your day with a leisurely breakfast and head to Dock Square, the heart of Kennebunkport. This charming area is filled with boutiques, art galleries, and local shops, perfect for a casual stroll. You’ll find some great spots for lunch or a snack here, and it’s a great place to soak in the local culture.
Lunch: The Clam Shack
No trip to Kennebunkport is complete without indulging in fresh seafood. The Clam Shack, located right by the water in Dock Square, is a must-visit for their famous lobster rolls. You can sit at one of the outdoor tables and enjoy your meal with a gorgeous view of the harbor—pure Maine bliss!
Dinner: Luca The Lost Fire Patio
For dinner, head to the Bohemian-style patio at Luca the Lost Fire Patio. This lively spot is perfect for pre-dinner cocktails or a romantic evening out. The atmosphere is upscale but relaxed, and the food is top-notch. If you’re in the mood for smoky, wood-grilled meats, don’t miss the sister restaurant, The Lost Fire Patagonian Grill Bar, known for its unique South American flavors.
Day 2: Outdoor Adventures & Local Culture
Morning: Ride to the Bush Compound Lookout
One of the best perks of staying at The Colony Hotel is the complimentary bicycles! We took full advantage of this on our second morning by cycling along a beautiful coastal trail that led us to the Bush Compound lookout. While the compound itself is private, the views of the Kennebunkport waterfront and the surrounding area are absolutely stunning.
Though the day was cloudy during our visit (which meant we didn’t get the clearest view of the compound itself), on a sunny day, you can actually spot the summer home of the Bush family—definitely a cool piece of history to see while you’re out exploring!
Dinner: Ultramar
For our final dinner in Maine, we treated ourselves to a fine dining experience at Ultramar. This restaurant combines the freshest local seafood with Mediterranean flavors, and the wood-fired cooking is second to none. It was hands down the best meal we had during our trip, and we’re already planning our return to enjoy it again!
For a more casual dinner option try: The Boathouse Restaurant!
For stunning waterfront views and a refined dining experience, The Boathouse Restaurant in Kennebunkport is a true standout. Located on the scenic Kennebunk River, this restaurant offers both indoor and outdoor seating with amazing views of the water, making it a perfect place to enjoy a sunset meal or special occasion. The menu focuses on fresh seafood and creative New England cuisine.
Day 3: Explore the Surrounding Areas
Morning: Visit the LL Bean Flagship Store in Freeport
On Day 3, we decided to venture out and take in some of Maine’s surrounding attractions. First up: the iconic LL Bean flagship store in Freeport. It’s a two-story mecca for outdoor lovers, offering everything from camping gear to hiking boots. It’s definitely worth a stop, especially if you’re an outdoor enthusiast (or looking for souvenirs!).
Afternoon: Portland Head Light
Next, head south to Portland Head Light, located in Cape Elizabeth just outside Portland. This is one of the most photographed lighthouses in the U.S., and with good reason. Built in 1791 under President George Washington’s command, it’s a stunning part of Maine’s maritime history. Located in Fort Williams Park, you can take a scenic walk, explore the historic fort ruins, or just relax and take in the breathtaking views of the Atlantic Ocean and rocky shoreline.
Pro Tip: You’ll need to pay for parking at Portland Head Light, but we felt the views were well worth it. The parking is free in the off-season (April-November), but it’s $2 per hour or $10 per day during the peak summer months.
Dinner: Eventide Oyster Co.
On your way back to Kennebunkport, stop by Eventide Oyster Co. in Portland for one of the best lobster rolls in the country!!! This trendy spot is known for its fresh oysters, inventive seafood dishes, and its famous lobster roll, which we declared our favorite of the whole trip. However, be prepared to wait, though—it’s a popular spot, but totally worth it! Definitely a must try for your 3 days in Kennebunkport!
Tip: While you are in Portland, stop at Duckfat for a pre-dinner snacks for the BEST french fries!!! A beloved local gem known for its mouthwatering Belgian-style fries and creative comfort food.
Conclusion: A Perfect Coastal Getaway in 3 Days
From the scenic harbor views to mouthwatering lobster rolls and a wealth of local history, Kennebunkport is the ultimate coastal escape. Whether you’re immersing yourself in the town’s natural beauty, soaking in its rich history, or indulging in delicious seafood, this 3-day itinerary ensures you’ll experience the best of what Kennebunkport has to offer.
Whether you’re planning a weekend getaway or a longer stay, three days in Kennebunkport will leave you with memories of stunning coastlines, incredible meals, and a true taste of New England hospitality. Trust us—this trip will be one for the books!
