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Kennebunkport, the small, picturesque coastal town about half an hour South of Portland, Maine, is a place where time seems to stand still and the chaos of daily life quickly fades to a distant memory. The slow pace of this beach town allows you to completely relax and unwind without being totally off the grid.

Dock Square in Kennebunkport | Photo by Compass + Twine

If the name of the town seems familiar to you, maybe it’s because it’s where the Bush family spends their summers. The Bush family compound is located at Walker’s Point, a beautiful bluff extending out into the ocean. A few hours in town and you’ll understand why they chose Kennebunkport to return year after year.

Locally owned boutiques, bakeries, art galleries and restaurants line the streets, while the harbor is filled with boats returning from a morning of lobstering. You could spend hours meandering the storefronts and walking along the water. Be sure and build up an appetite because Kennebunkport is chock full of decadent lobster joints. The lobster is fresh as can be and served in a simple style, which is perfectly fitting and reflective of the town itself. Read on for our guide to making your next trip to Kennebunkport a perfect one!

RELATED: 5 awesome Boston getaways that are not Cape Cod

Day 1

Arrive early and check in at The Tides Beach Club, a stunning yellow boutique property, and the only hotel right on Goose Rocks Beach.

The Tides Beach Club | Photo courtesy of The Tides Beach Club

Once the fog burns off, rent kayaks (available for guests) at The Tides and row out towards the Goat Island Lighthouse. You can even tour the naval landmark if you schedule ahead. Enjoy a quick lunch at The Tides then head into town to hop aboard the Pineapple Ketch. From aboard the sailboat, you’ll get a feel for the town by water and and soak in some awesome views of the craggy coastline. Wave hello to the Bush family when you pass Walker’s Point and learn all about local legends and lore from your Captain. Back at the hotel, grab a blanket and cozy up in one of their yellow rockers. Enjoy a sunset cocktail on the porch at The Tides, then hop on the hotel shuttle to Earth for an amazing farm-to-table dinner.

Day 2

Wake up at your leisure, then drive into town and grab a cup of joe at HB Provisions. The locally owned grocery-deli has everything you might want for a bite of breakfast and plenty to choose from if you’re hoping to pick up a Maine souvenir or two. Stroll around Dock Square, the buzzing center of town and pick up some handmade pottery at Good Earth, a husband-and-wife owned pottery studio where everything is made by them!

Good Earth | Photo by Compass + Twine

It’s time to delve deeper into the local fare, so lunch at Mabel’s Lobster Claw is a must. Order a bowl of chowder and a lobster roll (of course!) then do some shopping.

Lunch at Mabel’s Lobster Claw | Photo by Compass + Twine

Allot plenty of time to peruse Day Trip Society, a boutique filled to the brim with travel and adventure inspired goodies, then pop into Minka for nautical home goods and jewelry. You’ve walked off your lunch by now so you deserve a treat! At adorable ice cream shop Rococo, you’ll find funky flavors like red hot banana and salty sweet cream—both of which can be sampled before being piled high onto a cone.

Get your sugar fix but don’t ruin your appetite for dinner! Since David’s KTP doesn’t take reservations, enjoy a cocktail at the bar while you wait for your table. Begin your meal with a seafood tower—the local oysters are perfectly briny and smooth—then choose from myriad options on the long, delicious menu. And the night ain’t over yet: Hop aboard the Spirit of Massachusetts for live music and a nightcap before heading back to your hotel…

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Day 3

Enjoy breakfast at Salt & Honey, a homestyle breakfast joint in Dock Square, then  stroll along Gooch’s Beach. It’s a wide, dog friendly swatch of sand so you’re sure to see plenty of four-legged friends chasing after seagulls and frisbees.

Gooch’s Beach | Photo by Compass + Twine

You can’t visit Kennebunkport without lunch at the iconic shack on the Kennebunk River, The Clam Shack. Two-time winner of Tasting Table’s Lobster Rumble, the lobster rolls are served simply, tossed lightly in both butter and mayo and full of huge chunks of claw meat. A side of fried clam strips, some french fries, and a cold beer to wash it all down can never hurt, either.

The Clam Shack | Photo by Compass + Twine

With a full belly, head to Goose Rocks Beach and soak in the sun for the afternoon. The popular beach in town is perfect for a swim or afternoon of sunbathing.

For one last dose of Maine goodness, head to Nunan’s Lobster Hut for dinner. Open for over 60 years, the motto here is “We catch em. We cook em. We crack em. You eat em.” Order a steamed lobster with drawn butter and you’ll also receive a bib. Enjoy the sweet meat, served with chips, a roll, and a few pickles, then enjoy another Maine delicacy—blueberry pie.

Lobster from Nunan’s Lobster Hut | Photo by Compass + Twine

NOTE: New England is compact relative to the rest of the country, making side trips an enviable feature. Consider Portland (30 mins), Ogonquit (20 minutes) and Portsmouth, New Hampshire (1 hour) as very doable day excursions.


Tagged: Feature, New England

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Compass + Twine
Sarah Driggs and Lindsay Ridenour are the story-tellers behind the NYC-based luxury travel blog, Compass + Twine. Follow along on Instagram @compassandtwine as they unearth some of the best hotels and travel experiences around the globe. From scenic landscapes to local cafés, they reveal the true character of a destination, always highlighting the best place to stay on .

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