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Now, it’s time to zoom out a bit and observe your natural surroundings. The geography of Whidbey Island is defined by Penn Cove, a large aquatic inlet that transforms the verdant landmass into something of a squiggle. The land immediately surrounding Penn Cove is a historical reserve known as Ebey’s Landing, which has a long history of maritime trade thanks to the warm waters flowing from the nearby Skagit River. “We have abundant shellfish here,” Eric Cheong, one of the three owners who bought Captain Whidbey Inn in 2018, told me. “This has been a huge nexus of activity for millennia.”

“A perfect visit to Coupeville, the enchanting Pacific Northwest seaport from the 1998 cult classic, ‘Practical Magic’”

Repair to the historic Captain Whidbey Inn for a drink on the deck, a plate of Penn Cove mussels, and a relaxing snooze one of the inn’s guest rooms.

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Nestled among old fir trees along Penn Cove, Captain Whidbey Inn is a historic resort anchored by a stone-and-log main lodge built in 1907. Over the years, the property has been a boarding house, post office and girls’ school, until 2018 when brothers Mike and Matt French—along with designer Eric Cheong—took over and restored it to its former glory as a hotel. Modern touches include a restaurant and bar program by Chef Sean Prater and a collection of stand-alone cabins. A newly opened wellness studio and barrel sauna bring the hotel into the 21st century. “Each log and stone holds stories from the past hundred years but also the current moment,” Cheong says.

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To stay true to the history of Captain Whidbey, Cheong also worked with local archives to identify and keep historic photos and meaningful furniture at Captain Whidbey, adding that every family who has ever owned the property still lives on the island. He names the works of Rudolph Schindler and Mira Nakashima as inspirations for the Inn’s rooms, which range from nautical log cabin rooms at the main lodge to Scandinavian-inspired, modern spaces at the lagoon-side wood cottages, to complete cabin takeovers by Filson, Glasswing, We The Nomads and Edit Whidbey. Inside, original pine wood paneling is combined with warm, primary colors, cashmere carpet, locally-woven blankets and cedar-scented bath products by Seattle-based brands.

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Brothers Matt and Mike French, the visionaries behind the effortlessly hip Pioneertown Motel in the Southern California desert, have a knack for turning off-the-grid places into magnets of cool. Last spring, the duo, along with Ace Hotel Group alum Eric Cheong, reimagined a historic inn on Washington’s sleepy Whidbey Island.

The result: an adult summer camp with salty-dog, nautical soul. Set on the shore of Penn’s Cove, Captain Whidbey’s accommodations include a Captain’s Suite above the main tavern, where you can spot whales from your bed; and secluded cabins, each curated by a distinctive Northwest designer, such as Filson.

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Often overshadowed by the more prolific San Juan Islands, Whidbey Island refuses to be ignored. Located just north of Seattle, the 55-mile-long island is a mecca for outdoorsy folks, with enough watersports and hiking trails to plan an entire trip around. Make sure to pay a visit to Deception Pass State Park for some incredible cliff-top views, then set up camp at the Captain Whidbey, a historic inn originally built in 1907 that was rebooted in 2019.

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The result: an adult summer camp with a Moby Dick-meets-Moonrise Kingdom vibe. There are vintage photos on the walls, plus an original stone fireplace anchoring the lobby and a logo inspired by the handwriting of a past owner’s wife. Upstairs, 12 lodge rooms still have creaky floorboards, shared bathrooms, and a library of classic sea tales, but now there’s also a rotary phone with a direct line to the bar down below. Across the street, 14 Lagoon rooms have a Scandi sensibility with interiors influenced by Mira Nakashima and Aino Aalto. And just above the shores of Penn Cove, four private cabins have each been outfitted by Pacific Northwest tastemakers including Filson and Whidbey’s own modern mercantile, Edit. The property is full of hidden secrets, ranging from secluded firepits and hammocks to a poem written in Morse code along the bar. DJ brunches and sunset happy hours have been big hits for both locals and out-of-towners.

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