Kennebunkport, Maine


I’ve always wanted to visit coastal Maine, eat an excessive amount of lobster, sit in adirondack chairs and sip white wine, go sailing, eat more lobster. Rinse. Repeat. 

So that’s exactly what Brian and I did over (a slightly extended) Labor Day weekend. 

I agonized a bit over which town to stay in. Bar Harbor? Portland? In the end, an adorable inn featured on Jetsetter drew me to Kennebunkport. And, in fact, we stayed at that very inn. 



Captain Fairfield Inn is a charming B&B located in the heart of KPT (as the locals call it) and is walking distance to Dock Square, the hub of the town. We landed in Portland crazy late after some travel delays and when we finally arrived at the inn, the innkeepers had left our key waiting for us with instructions to check in the following morning. We helped ourselves to the cute “honor bar” in the guest pantry and grabbed two local microbrews before heading up to bed. Each of the inn’s rooms is uniquely decorated and we opted for the modern-meets-classic Rachel room. It was perfect for a cozy weekend getaway (though we would have loved a more updated bathroom). One of my favorite touches at Captain Fairfield? Breakfast in bed. Should you miss the communal breakfast in the morning due to sleeping in (which was us every single morning except for our last day), the innkeepers will drop it off at your door along with a pot of delicious coffee. 


On our next trip to KPT – and there will definitely be a next trip – I’d love to stay at The Boathouse, a new boutique hotel located right on the harbor with killer views and a really delicious restaurant, David’s KPT. The location is perfect if you love to be in the heart of things. The luxurious Hidden Pond hotel is also on my Kennebunkport bucket list, as well as its famous restaurant, Earth. We spent quite a bit of time hanging out closer to the beach at Stripers, the restaurant at the Breakwater Inn & Spa. And while the rooms may not be entirely decorated to my liking (so. much. blue), access to Stripers and the lovely adirondack chairs that dot the lawn overlooking the river and the ocean is my idea of heaven.



If I told you that we at lobster rolls every single day while we were in Maine, would you judge me? Like 5 lobster rolls in 4 days? (Yes, we doubled up on the last day.) Well, we did. And it was glorious. 









 Our absolute favorite was the brown butter lobster roll on a steamed bun from Eventide Oyster Co. in Portland. Not only did the lobster roll change my life, but their oysters were hands down the best I’ve ever had. The selection was overwhelming, so I told our server to pick his favorites for us. The best traditional lobster roll came from Stripers, which we enjoyed on our last day with a rainy view of the river and the Atlantic (plus a pretty tasty bloody mary). And the “check that one off the bucket list” lobster roll came from Kennebunkport’s legendary Clam Shack. We opted for the “butter and mayo” option. And yes, our pants fit significantly tighter after this trip. 

Other favorites: the baked feta, craft cocktails and stellar wine list at Old Vines, the dessert and dirty martinis at David’s KPT, happy hour by the fire pit at Tia’s Topside, beer flights at Federal Jacks, classic upscale New England dining at One Dock, the fried clams at Pilot House


Our number one objective in Kennebunkport was to R-E-L-A-X. And we were pretty successful with that. We slept in. We ate breakfast in bed. We strolled through Dock Square and window shopped (and really shopped). We sat in many assorted outdoor chairs and enjoyed the view and each other’s company. We ate a lot. We drank… well, a lot. We caught caught in a freak thunderstorm one night while walking home from dinner and ended up dancing and laughing in the rain. 

But we did do a few less indulgent things. 


We went sailing on the Pineapple Ketch on a beautiful evening. We would do this again in a heartbeat.


 And we ventured out on a lobster cruise on Kylie’s Chance. The water was a little rough for my liking, but it was fascinating. 




On the first evening in Kennebunkport, as we watched the sunset from a sailboat, I looked at my husband and told him I didn’t want to leave. Or, at the very least, could we come back next year? And the year after? He enthusiastically agreed. And I’m already planning our 2014 trip.