Sperry Sets Sail With ‘Yacht Rock’ Lifestyle Collab At Maine Hotel

Deck shoe style meets harborside hotel vibes.

Yachtsman_8135_FNL| Credit Mark Thayer
Mark Thayer

Mark Thayer

Heritage boat shoe brand Sperry has dropped anchor at a Maine hotel for a coastal chic lifestyle collaboration designed for road trippers seeking a low-key maritime getaway. Sperry joined forces with the Yachtsman Hotel & Marina Club in Kennebunkport for a decidedly preppy partnership complete with a “Yacht Rock Bar” and craft cocktails inspired by the brand’s iconic boat shoes, including the “Official Prep” and the “1935,” honoring the year company founder Paul Sperry invented the world’s first non-slip deck shoe.

The Yachtsman harbors 30 waterfront bungalows with private terraces overlooking the same tranquil marina where former president (and longtime Kennebunkport resident) George W. Bush docks his triple-engine powerboat. 

The Yachtsman Hotel & Marina Club

There are ample no-contact COVID-19 precautions, including room check-ins via text, daily breakfast bags hung on your door and reserved parking in front of the vibrantly-decorated rooms. The Yachtsman is just a short stroll to downtown Kennebunkport and some of America’s best lobster rolls at Clam Shack, and near scores of lobster-focused eateries, including Nunan’s Lobster Hut, Mabel’s Lobster Claw, Arundel Wharf, Port Lobster, Pearl Kennebunk and Cape Pier Chowder House. 

The Yachtsman Hotel & Marina Club

The hotel, which boasts a unique floating barge pool, is also convenient to the brisk ocean waters of Goose Rock Beach and the more intimate Colony Beach, as well as sailing, fishing, kayaking, canoeing, lobster boat tours, and other waterborne activities. 

Sam Waxman

Sperry, which has been a footwear mainstay of boaters and beachgoers for more than 85 years, aims to use the hotel partnership to further imbue The Yachtsman with Sperry’s New England seaside style, much as Rust Belt watchmaker Shinola did with its launch of a branded hotel in Detroit. 

The Yachtsman’s seafaring aesthetic prompted Sperry to set sail with the hotel’s parent company, Kennebunkport Resort Collection, a veritable hospitality industry whale beached in this quaint coastal town. It operates nine local restaurants and hotels including Hidden Pond, The Tides, The Boathouse Waterfront Hotel, Grand Hotel, Cape Arundel Inn, Cottages at Cabot Cove, Kennebunkport Inn, and Lodge on the Cove.

Yachtsman Hotel & Marina Club

“We’re a global brand, but we were born right here in New England so we’re always looking for ways to connect with our consumers here locally.” said Melissa Romig, marketing director for Waltham, Mass.-based Sperry. “From the waterfront bar to the top-notch service, the Yachtsman experience was exactly what Sperry wanted to be a part of.”

Sperry, which occupies a hallowed perch among classic boat shoe makers, has lately been refreshing its prep image with campaigns featuring singer and brand spokesperson John Legend. But it’s Sperry’s signature Top-Siders that have burnished the brand’s reputation for decades with a rich stylistic history. 

John Legend decked out in Sperry gear

Paul Sperry, a U.S. Navy veteran and avid inventor, decided to make a non-slip boat shoe after slipping and falling on the deck of his sailboat, The Sirocco, late one night on the Long Island Sound. Legend has it that Sperry was inspired by the texture of his cocker spaniel Prince’s footpads, which never seemed to slip, even in icy conditions. So he cut grooved patterns into a rubber sole and glued it to the base of an old pair of canvas sneakers, inventing the first non-slip deck shoes in 1935. 

Sperry’s prototypical deck sneakers generated buzz among the sailing set and were ordered up by a small outdoor outfitter company called Abercrombie & Fitch. In 1937, Sperry followed up his original canvas version with a deck shoe made from specially tanned leather that didn’t corrode in saltwater. That shoe utilized classic moccasin toe stitching and “saddle” lacing, where the shoelaces wrap around the ankle to tighten up the collar. The same construction is still used today in Sperry’s Authentic Original Top-Sider, or “A/O”, aka the original boat shoes.

The Yachtsman Hotel & Marina Club

The Sperry Top-Sider was issued to U.S. Navy sailors and Naval Academy cadets in 1940, immortalized in 1980’s The Official Preppy Handbook and worn by a young Tom Cruise in 1983’s Risky Businesseven though everyone only remembers his Ray-Ban Wayfarers. More recently, Pharrell Williams and Kanye West were photographed rocking Top-Siders with breezy summer attire, and Sperry launched limited-edition lines with J. Crew, Band of Outsiders, Rowing Blazers and GOOP. The classic leather Top-Sider has long been a favorite summer slip-on, and can reasonably go from boat to bar to boardroom (and back again) if the wearer is sufficiently pressed for time.


The Yachtsman collab is merely Sperry’s latest bid to broaden its storied boat shoe legacy. The hotel is currently offering a special “Therapy by the Sea” package through Oct. 31, which starts at $1,295 and includes a two-night stay at the Yachtsman, two pairs of Sperry shoes in your room upon arrival, cocktails at the Yacht Rock Bar by Sperry, and a two-hour kayak or canoe rental from Kennebunkport Marina, right next to the Yachtsman. 

Sam Waxman

The outdoor Yacht Rock Bar is the kind of place where vintage Christopher Cross or Michael McDonald tunes might gently waft through the air while socially-distanced guests tipple cocktails overlooking the marina. The pop-up bar’s nautical vibe features colorfully-striped garden furniture, driftwood-inspired tables, Adirondack chairs, a fire pit, and an Instagram-ready photo backdrop modeled after the bow of a boat. 


To book a stay at the Yachtsman Hotel & Marina Club, go here.