Kennebunkport Maine
Kennebunkport Guide
What to do in 2 nights in Kennebunkport, Maine
Getting There:
Fly into Portland, Boston or Bangor. With quick/cheap flights from DC we drove up from Logan and it’s an easy drive straight up 95 (under 2 hours).
Stay:
There are tons of Airbnbs if you are traveling with a family or group which are probably more economical, especially if you plan on staying for a longer period of time. But since it was just us and only a couple nights before heading to a wedding in another part of Maine, we opted for the hotel route.
The Colony Hotel - While we didn’t stay there, this historic property is a must to stop by and check out. We arrived before our room was ready so we had a poolside lunch overlooking the Cape. It’s a bit further from the action downtown but you’ll have access to a small private beach. It’s also a stone’s throw from the Bush’s home (more on that below).
Yachtsman Hotel & Marina Club - Hands down was the epitome of everything you’d expect from Kennebunk. A converted motor lodge turned upscale boutique hotel has classic design mixed with modern amenities and upgrades (subway tile and gold bathroom accents). Each room has its own private patio on the waterfront and a mini kitchen area with a fridge. There’s a dockside bar and floating pool in the marina (omg) not to mention free bikes, kayaking and welcome bubbles and whoopie pies. I loved every second of our two nights here and the Yachtsman Hotel made our trip so special. Pro tip: we snagged a deal on Hotel Tonight AND breakfast delivered to your doorstep is included in your stay!
White Barn Inn - If you’re willing to splurge, the White Barn Inn (an Auberge property) checks all the boxes. After hearing so many good things about this upscale cottage + spa, I had to see it for myself and popped in one morning to check it out. While gorgeous from the outside (peeked in the pool area and restaurant) I personally think it’s a little far from the action for the price (although you are closer to the public beach). But, I’m sure it’s lovely and lives up to the hype!
Eat + Drink:
Lobster, lobster and more lobster. Here are some highlights to get your fix!
Boathouse - Chic restaurant on the water in the middle of town. Walked here from the hotel on the first night and split “lobsta in the rough” (aka where you crack it yourself).
Allison’s - One afternoon it started raining while we were out exploring town so we ducked into a local sports bar for a beer (22 rotating taps).
The Clam Shack - The infamous spot to get, you guessed it, clams! They have boiled lobster, crab and other seafood sandwiches served on freshly baked buns and served with sides. There’s always a line but it moves fast!
Mabel’s Lobster Claw - A cute little house and one of the Bush’s favorites. You can tell it’s all locals and regulars here. We sat on the patio for dinner our last night (reservations strongly encouraged).
Spirit of Massachusetts - Floating bar on an old sailboat. We had drinks here after the Boathouse - an ideal spot for a romantic pre-dinner drink or post-dinner nightcap.
Do + See:
Walker’s Point - a short 5 minute drive from downtown, you can get a glimpse of the Bush compound (they were in residence when we were there and saw them walking with their pups). Also an anchor memorial for Barbara and overlook spot to take photos.
Ride Bikes & Shop - there are too many cute stores to name but Day Trip Society was my favorite. And I love the fact that no one locks their bikes up (quite the contrast coming from DC). Most have Bush souvenirs or other preppy shirts, totes and koozies to say you’ve been to Kennebunk!
First Families Museum - Believe it or not, there is a historic mansion turned historical society with artifacts and memorabilia from the Bush family(s). There’s a full museum but the Bush part is just a room that they help curate each year. Be sure to check out Barbara’s garden nearby.
Water Sports, Lighthouses & Beach - What trip to Kennebunk would be complete without some water activities.
Lobster Tour - This last-minute idea was the best decision of the trip. There are a limited number of non-commercial wooden lobster boats that have licenses to catch and release for educational purposes and we did the family-owned Rugosa. It was so educational and entertaining too. Pro tip: BYOB and book in advance.
