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How to Spend a Weekend on Washington’s San Juan Island

Two Dallasites share what they love most about this Pacific Northwest jewel.
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In Good Company: San Juan Island is the second largest of the 450 islands that make up the San Juan Islands archipelago. Bill Gates is one of several big names who own property in the islands. Illustration by Andrea Chavez

How to Spend a Weekend on Washington’s San Juan Island

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Designer Chad Dorsey and builder Kurt Bielawski fell in love with Washington state’s San Juan Island more than 20 years ago, in awe of the archipelago’s natural beauty. They lovingly established a second home there back in 2016, and have been enjoying summers there ever since.

We chatted with Bielawski and Dorsey about why they fell in love with this Pacific Northwest jewel and how others can make the most of their trip to the island.

Why Visit?

Get in touch with nature.

San Juan Fields

From shimmering water and wooded coastlines to snow-capped mountains in the distance, there’s a little bit of everything here. Be prepared to spot some wildlife too; the couple says they frequently see foxes and eagles on the island and orcas, flying fish, and jelly fish in the water.

Whet your appetite.

Fresh Seafood Linguine Clam DishWhether you want to try out your culinary skills or let someone else do the cooking, the food and drink options on the islands are top-notch. Stellar produce, fresh seafood, and inventive spirits are all in heavy supply. “There are some really interesting restaurants, not only on our island—you can island hop,” says Bielawski. “It’s a great place if you’re a foodie.”

Choose your own adventure.


Hotel de Haro at the Roche Harbor ResortThere’s a variety of extracurricular options here to suit your speed, whether you want to unplug and unwind or stay active. Bielawski and Dorsey love to sea kayak and hike but spend plenty of time cooking or reading at home. The Roche Harbor resort and Friday Harbor areas—both bustling in the summer months—have great eateries and well-curated shops.

How to Get There

Fly into Seattle (SEA) or Vancouver, British Columbia (YVR). Drive to Anacortes, Washington, to take the Washington State Ferry to the Islands. Or take a seaplane to San Juan Island’s Roche Harbor or Friday Harbor. Kenmore Air and Friday Harbor Seaplanes both fly direct from Seattle. (Bielawski recommends first-timers take the ferry for the most picturesque approach.)


On the Itinerary

Bielawski and Dorsey’s must-dos for a trip to San Juan Island

Hiking at American Camp Cattle Point with Lighthouse

Hike American Camp, located on the south end of the island; English Camp, on the north side; or Mount Dallas, on the west side.

San Juan Fields

Picnic at Cattle Point, located on the southernmost tip of the island. “A sunny day is a must for this,” says Bielawski, who brings a takeout Cuban sandwich from the Spring Street Deli in Friday Harbor.

Susie's Mopeds with Bikes, Scooters, and Coupes

Rent a ride through Susie’s Mopeds, the easiest way to get around the island. They have e-bikes, single mopeds, and two-seater scoot coupes.

Killer Ocra with Whale Watching

Book a sea-kayak or boat tour to get up close and personal with orcas. “It’s amazing to see them in person,” says Bielawski.

Alpaca from Krystal Acre Farm

Enjoy pastoral views and feed an alpaca or two at Krystal Acres Alpaca Farm. Shop throws, hats, socks, and more—all made from alpaca fiber—in the on-site store.

San Juan Buildings at Port

Have happy hour at Madrona Bar and Grill in Roche Harbor. Come at sunset to take in the nightly “Colors Ceremony,” in which the flags are lowered and national anthems are played. To secure a spot on the deck, it’s best to make a reservation.

San Juan Distillery & Tasting

Imbibe at San Juan Vineyard, San Juan island Brewing Company, or San Juan Island Distillery.

Westcott Bay Shellfish Company

Dine at one of the island’s many delicious restaurants. For breakfast, grab donuts at Lime Kiln Cafe. For lunch, Bielawski and Dorsey like the BBQ oysters at Westcott Bay Shellfish Company or the salmon burger at Downriggers in Friday Harbor. Dinner favorites include the picturesque Duck Soup, McMillin’s Dining Room for prime rib and a martini, or Vinny’s Ristorante for unassuming Italian fare. During the week, Bakery San Juan is a must for bread, pizza, and cinnamon rolls.


Jessica Otte

Jessica Otte

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Jessica Otte is the executive editor of D Home and D Weddings. In 2006, she helped launch D CEO as…

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