If you’re searching for a weekend away in a picturesque coastal town in Maine, look no further than Kennebunkport. With so much to explore in this charming town, I’ve created a Kennebunkport weekend itinerary to help you make the most of your time there. This itinerary will ensure a memorable long weekend in Kennebunkport, from the best restaurants and drinking spots to the top things to do.
How to Get to Kennebunkport
When planning a trip to Kennebunkport, you’ll have two airport options: Boston Logan International Airport and Portland International Jetport. The Boston Logan Airport is approximately a 90-minute drive to Kennebunkport, while Portland Airport is only a 30-minute drive. When I went in July, I found that airline tickets to Portland were significantly more expensive than flying into Boston.
If you’re flying into Portland or planning a Maine road trip, be sure to check out my Ultimate Guide to Portland and my suggestions for How to Spend on Day in Portland for the best tips on what to see, eat and do!
Getting Around Kennebunkport
We rented a car, which was needed for certain restaurants like The Lost Fire and those in Cape Porpoise, but overall, Kennebunkport is a very walkable town. If you plan on venturing outside of downtown, a rental car is ideal, as I could not find any Uber or Lyfts readily available. Biking is also a good option for exploring, and many hotels offer bikes to their guests.
If you plan on renting bikes, there are two options in town:
Mainely Bicycle
Half day bike rental (4 hours): $29/adult
Full day rental (24 hours): $39/adult
Coastal Maine Bike
Half-day bike rental (4 hours): $34/adult
Full day bike rental (24 hours): $42/adult
There are also multiday rental options available
Where to Stay in Kennebunkport
I recommend staying at the Grand Hotel. We stayed here our first time visiting and loved it. Located in the heart of town, it’s within walking distance to the best activities and restaurants in Kennebunkport. The hotel also provides bike and kayak rentals, complimentary continental breakfast, and access to The Yachtsman’s pool.
Day One
Once you’ve settled into your hotel, walk to The Boathouse restaurant for lunch. This lively spot has delicious food and a trendy atmosphere. Ask for a table on the patio to have views of the Kennebunkport River. In case of a wait, put your name down and explore Dock Square; the restaurant will notify you via text when your table is ready.
The combination of waterfront views and high-quality seafood makes this place the ideal starting point for your weekend in Kennebunkport.
After lunch, explore the shops in town. There are many to visit, but my favorites are Bliss and 173 Mercantile. If shopping isn’t your thing, take advantage of the complimentary hotel bikes and head over to Gooch’s Beach. Just under a mile from the Grand Hotel, this sandy beach is the perfect spot to walk or lay in the sun and gives you views of Maine’s rocky coastline.
After exploring the town or the beach, head to The Spirit of Massachusetts for a drink and appetizers. This is a historic ship on the Kennebunkport River that offers a unique setting for a memorable experience. I highly recommend trying the prawns and The Sea Cucumber- they were my absolute favorites on the menu.
You must go to Luca, the patio at The Lost Fire for dinner. I thought this was one of the best restaurants in Kennebunkport. It offers the same menu as The Lost Fire but on a bohemian patio in the woods. The ambiance was magical, with twinkling lights strung along the trees, Adirondack chairs circling a fireplace, and drinks served out of a small barn. The food was excellent—I had a burger and fries and Tim had a filet. Although it’s about a ten-minute drive from town, this restaurant is a must-try for anyone visiting Kennebunkport. I recommend making a reservation in advance.
If you’re in the mood for an after-dinner drink, stop at Ryan’s Corner House Irish Pub, just across the street from the Grand Hotel. Relaxing around the outdoor fireplace while listening to live music is the perfect way to end your first night in Kennebunkport.
Day Two
Start your day with the hotel’s complimentary breakfast, or walk to Dock Square Coffee House.
When it comes to activities, Kennebunkport offers a variety of water activities, but I recommend taking the Rugosa Lobster Tour. A lobster cruise offers a unique look at Maine’s iconic lobster industry. As you set out on Maine’s coastline in a working lobster boat, you can sit back and relax while the crew pulls traps from the ocean or get hands-on and help with the process. It’s an educational and picturesque experience all in one.
Rugosa Lobster Tour: Located in Kennebunkport, the Coastal Lobster Tour offers a 75-minute cruise starting at $49 per person. A private charter is available for $900.
If you don’t want to commit to a tour, take the hotel’s complimentary kayaks and get out on the Kennebunkport River. Kayaking is a peaceful way to explore the town’s waterways and waterfront homes. You might even spot some wildlife, like seals or herons.
For lunch, go to Casa Seventy-Seven It’s located in Cape Porpoise, a more laid back side of Kennebunkport, where you can watch the fishing boats come and go. Inside, the restaurant has a modern vibe, but we sat at a bistro table outside, right by the water. I ordered a lobster roll and paired it with a limoncello spritz. It’s the ideal spot to enjoy coastal Maine.
For a pre-dinner drink, walk to the Kennebunkport Inn and sit on the patio at their outdoor bar. You’ll be surrounded by twinkle lights and hydrangeas and will enjoy live music.
After drinks, walk across the street to Chez Rosa for dinner (you should make a dinner reservation in advance). This enchanting French restaurant is considered one of the best restaurants in Kennebunkport. The greenery draped across the walls and ceiling, French bistro chairs, and white marble tabletops make this one of my favorite restaurant ambiances. I started with a half-dozen oysters, but they were so fresh that I had to order six more. We also had French onion soup, steak frites, and crème brulee.
Old Vines Wine Bar is just a short walk from the Grand Hotel. This relaxed wine bar with a cozy outdoor patio is the perfect destination for a post-dinner drink.
Departure
Leaving Kennebunkport can feel bittersweet, but you can still end your trip on a high note!
If you’re driving back to Portland, leave early and stop at the Portland Head Light. It’s one of the most iconic lighthouses in Maine, and the views are some of the prettiest I saw on my trip. Perched on rugged cliffs, the lighthouse offers ocean views and picture-perfect scenery. The surrounding Fort Williams Park is also a great spot to stretch your legs and capture some photos before you leave. If you’re not quite ready to say goodbye to Maine’s seafood, there’s even a lobster roll truck on-site for one last roll before you leave.
If you’re driving back toward Boston, Frisbee’s Wharf in Kittery, Maine is the perfect spot to wrap up your trip. This waterfront restaurant offers a relaxed setting with views of the harbor, making it the ideal place to unwind before heading home. Watch the boats go by while enjoying some of the best seafood in Maine.
For even more inspiration, take a look at my Ultimate Kennebunkport Travel Guide for top tips on where to stay, eat, and explore. If you’re short on time, my One Day in Kennebunkport Itinerary covers the best ways to make the most of a quick visit!
