While Kennebunkport receives the most visitors in peak summer, the charm and allure of the Port continues year round. In fact, locals love the off-season, fall and spring especially when you can enjoy summer like weather with far less vacationers in Dock Square, the beaches and boating. Also the best dining and lodging spots in Kennebunkport adjust their prices after peak season with special promotions, happy hours deals, and of course more availability – even at luxury hotel properties like Captain Lord Mansion, the Breakwater Inn and The Boathouse Waterfront Hotel and the cozy but sophisticated Inn at English Meadows.
When it comes to lapping up the sweetness of luxury, the weather doesn’t even matter. Rain or shine, warm or cool, there’s always a place for you to sit pretty in Kennebunkport, to spa, to shop, to sip cocktails, to saor lobster! Here’s how to lavish in luxury in Kennebunkport…
Luxury Stay
Captain Lord Mansion combines history, sumptuous comfort, and prime proximity to Dock Square. Not only is this quaint B&B in Kennebunkport an inspiration for romance with exquisitely tasteful antique decor, but the inn also has an onsite spa service and many rooms have working fireplaces and spa tubs. Its ahsort walk from Captain Lord to the waterfront and to Dock Square’s shops and bistros.
Pub Dining
Allisson’s Restaurant is like a “Cheers” to the local people of Kennebunkport and those traveling to the seaside town. Though this restaurant in Kennebunkport center doesn’t boast richness and extravagance, its not fancy, its casual and fun, and the award-winning chowder and lobster roll are just that. Thumbs up. It’s a laid back atmosphere with expansive bar menu that will turn just one drink with dinner to asking for more “bee-ahs”.
Fine Dining
Boathouse Waterfront Bar and Restaurant offers great cuisine, and a gorgeous setting overlooking the Kennebunk River. Lobster is always on the Boathouse menu along with creative entrees and craft cocktails, plus there’s a lobster raw bar piled high with fresh oysters, shrimp, clams and Maine’s best crustacean. If you want a romantic, intimate experience with your dinner, go to the White Barn Inn – Maine’ s most lavish five-star dining, a five-course prix-fixe menu at a beautful setting, just across the Kennebunk River in the Lower Village. Oh, and it’s a romantic place to for an intimate dinner with your lover too. Many-a-proposals have been made here after relishing in elegantly presented menu items.
Earth at Hidden Pond, though a cool casual vibe, has award winning cuisine too. Sit at the bar and enjoy the twinlkling lights under birch trees, or ask for the private potting shed and prepare to be amazed by the food, prepared in the open concept kitchen over a wood fire.
Chocolate
Maine is known for its saltwater taffy, and homemade mapel candies, and chocolate covered blueberry. The Candy Man in Dock Square certainly lives up to the hype, offering all these unique Maine-made treats, plus the penny candy you remebmer as a kid. But it’s also expert in chocolatey treats, some of which sound like something from a cocktail menu including the Kahlua White Russian. These turtle-y delights come in two sizes: a small bite or a larger turtle for sharing (or not).
Night Life
Most incorrectly assume that the Kennebunks are not for the place to howl at the moon, but people know how to let loose in the Bunks. The Pilot House is where the lobster fishermen and locals go for a drinks and to listen to live music like Pat Foley or the Lower Village People. Old Vines Wine Bar is a classic tasting room style gathering spot with a fabulous wine list, delicious tapas food and live local music. The bartenders here are fantastic too. For a contemporary cocktail setting, Burleigh at the Kennebunkport Inn sets a hip tempo in a pubby club atmosphere. Pedros is the Mexican joint in town with great tacos and marguaritas.
Best Luxes in Life are Free

The last taste of luxury in Kennebunkport is one you don’t have to pay for. Free it may be, but sunsets in Kennebunkport will make you feel like the richest man/woman in the world.
Best Sunsets in Kennebunkport
The best sunset view is from Stripers Waterside Restaurant at The Breakwater Inn. Or drive to St Anne’s Church along Parson’s Way, there are park benches and limited parking, and watch the sunset over the sea… priceless!
For a small town that attracts families with its beaches and adult visitors for its slow paced atmosphere (I refrain from using “older generations” here because 60 is the new 40), the Kennebunkport Dock Square/Lower Village is a happening place. It’s the place for any generation to spurge and live in luxury.
For lodging in The Kennebunks, see our Kennebunkport Lodging Guide.
See our Kennebunkport Events Page for all the goings on all year long in the Kennebunks.
Photos and Content Copyright KennebunkportMaineLodging.com 2019
