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Wherever you’re heading, the sea will be there – a steady promise every day. We’re ready for a summer on the bright side, full of moments to appreciate how far we’ve come. Let’s celebrate a new course forward – in shoes that ground us and inspire us to head out on a new journey.

This summer, we’re bringing you to the sea in style. We’ve partnered with the Yachtsman Hotel & Marina Club to create a ‘Therapy by the Sea’ package. Get ready to reset by the sea in Maine’s most stylish new hotel destination with seven of our local ambassadors. Hitting the roads from all over the Northeast, they embarked on a journey to the sea for a socially-distant weekend. These ambassadors include Azulena Royer, Caroline J, Danielle (AKA Boston Brunch GuideGarrett Swann, John Philp Thompson III, Kyle Finn Dempsey, and Lisa Jean-Francois.


Anchored between downtown Kennebunkport and local beaches, the Yachtsman is a serene waterfront escape that brings you a breezy feeling of summer freedom. With 30 vibrantly decorated harbor-front bungalows, each with private terraces overlooking waterfront views, and luxe amenities like complimentary breakfast baskets and a one-of-a-kind floating barge pool docked steps from the room.

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Sperry’s heritage of innovation and love for the sea meets the Yachtsman’s handcrafted approach to hospitality. Find coastal spirit at every turn, from the Yacht Rock Bar by Sperry—an al fresco, waterfront setting inspired by summer-state-of-mind—to the views of the calming tidal river shimmering in the summer sun and flowing out to the ocean. Like summer, this curated experience is fleeting: experience these unique offerings from July 1st through October 31st 2020.

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Like our Sperry ambassadors, enjoy the quintessential New England summer vacation, exploring all that Kennebunkport has to offer. A few can’t-miss experiences to make the most of the surroundings and your “Therapy by the Sea” package at Yachtsman: a classic Yacht Rock party with craft cocktails, a bike ride down Ocean Avenue, and lobster boating off the coast. The official uniform for all these authentic original experiences? A pair of tried-and-true Sperrys of course.

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Whether you’re new to the genre or already addicted, there’s nothing quite like the simple pleasure of setting sail with some smooth rock classics. Happy hour at the Yacht Rock Bar—outfitted in an eclectic mix of bright white garden furniture, bistro sets, driftwood inspired high-top tables and Adirondack chairs—includes custom cocktails served alfresco from a menu inspired by Sperry’s heritage and all the freedom of the yacht rock lifestyle. There’s even a fire pit to sit around while you sing along.


Dedicate a leisurely day to explore the pristine coast by boat or bike. From the rugged coastline in the warmer months to the breathtaking display of brilliantly colored leaves that begin around September, there’s plenty to love in Maine. Our ambassadors explored every nook of Kennebunkport. There’s something restorative about the seaside air of New England.

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Take a cue from our ambassador Azulena and design your own perfect beach day to include watching the surfers, enjoying the waves, and giving your feet the warm sand treatment. Soak in the views that make people fall in love with Maine: a quiet cove, weathered shingle houses, a safe harbor full of working lobster boats, and the magical islands of Cape Porpoise Harbor and the Goat Island Lighthouse. Bring a lunch to enjoy overlooking the harbor.


Another dream afternoon in Kennebunkport? House peeping around the vibrant summer community. Our ambassador Caroline‘s bike ride around the beaches featured beautiful ocean views—and some seriously stately homes. Mix in some stately nature, too. Head northeast of Kennebunkport for Goose Rocks Beach, Fortune’s Rocks, the craggy shore of Biddeford Pool and the East Point Sanctuary, Wood Island Light, and Hills Beach.


Love to learn? Ask the concierge about a lobstering adventure.  Hear the lore of the Kennebunkport coastline while soaking in the sights. Out on the blue Atlantic, we got to know the ropes of lobstering, pulling up traps and learning how lobstermen decide whether a lobster is dinner worthy. Garrett Swann‘s footwear for this authentic original experience? Sperry boat shoes are a must for a non-slip experience on-deck.

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