Slow-paced island life, farm-to-table cuisine, and intimate accommodations make for the perfect winter escape. 

Though the San Juan Islands aren’t as popular during the drizzly season, the relatively deserted towns make for a crowd-free adventure. The slow pace allows shop owners and artisans linger with customers. Cloudy days offer their own kind of beauty. Mist often clings to fields and shrouds shores, lifting like a translucent curtain.

The hikes remain beautiful and wildlife plentiful during the fall and winter months. But don’t feel pressed to go exploring. These cuddle-worthy destinations feature cozy fireplaces that may keep you indoors all day and all night. Whether it’s a solo getaway or a party of two, the San Juan Islands offer the perfect mix of solitude and hospitality. 

The Edenwild Boutique Inn, Lopez Island


Photo provided by Edinwild Boutique Inn

While the inn does offer complimentary WiFi, it’s a TV-free zone best designed for unplugging. The spacious rooms offer full baths and unique amenities like large soaking tubs and wood-burning fireplaces. Plus, mornings here start with scratch-baked goodies, fresh fruit parfaits, and Lopez Island coffee.

Dinner: Ursa Minor

Ursa Minor Lopez

Photo by Portia Smith

Praised by The New York Times for its commitment to Lopez-sourced ingredients, Ursa Minor has become a beacon for visitors and locals alike. While their menu can change daily, keep an eye out for anything pickled. Their ‘Ursa Minor Ferments’ project transforms a wide variety of fresh goodies into sour-salty delights. (Currently only available for takeout.)

Small Excursion: Gentle Bike Ride

With its relatively flat terrain, Lopez is one of the gentlest islands to explore on two wheels. Rent a bike from the inn and take a spin around.

Tucker House Inn, San Juan Island

Tucker House Inn

Located just steps from Friday Harbor Marina, the Tucker House Inn is a quiet escape that also gives you walkable-access to San Juan Island’s biggest town. The Victorian buildings and cottages were built in 1898 and have been elegantly maintained. Eco-friendly and pet-friendly, this idyllic destination is particularly well known for its two-course daily breakfast.

Dinner: Coho Restaurant

Pasta at Coho on San Juan Island

Tucked within a historic craftsman house, located less than two blocks from the Tucker House Inn, Coho specializes in Pacific cuisine with a Mediterranean flair. Particularly delightful are the hand-rolled pastas, like the pappardelle that comes in a luscious pork and lamb Bolognese. (A generous selection of gluten-free and vegan options is also available.)

Small Excursion: Look for Whales at Lime Kiln Lighthouse

While it’s not prime whale watching season, Lime Kiln Lighthouse is known as one of the best land-based whale watching destinations in the world. Who knows, you might get lucky!

Outlook Inn, Orcas Island

Outlook Inn on Orcas Island

Photo by Ilias Schneider

It’s hard to rival Outlook Inn’s prime location. Tucked at the edge of Eastsound, it feels like it’s worlds away while still being just steps from some of the Island’s best novelty shops, bakeries, and restaurants! Plus, the newly added luxury bay view suites rest just above the water’s edge, offering high-end modern luxuries and exceptional views.

Dinner: New Leaf Café

New Leaf Cafe Scallops

Photo by Ilias Schneider

Tucked within Outlook Inn, New Leaf Café is a far cry from restaurant fare. The menu is an ode to the islands, featuring French-inspired Northwest cuisine where seafood rules and sauces might make you lick the plate. 

Small Excursion: Sample Beer at the Island’s Brewery

Roughly a mile from Outlook Inn, Island Hoppin’ Brewery offers locally-brewed pints and taster flights.

Friday Harbor House, San Juan Island

Friday Harbor House

Photo provided by Friday Harbor House

Only two blocks from the Friday Harbor seaplane dock, Friday Harbor House elevates seaside lodging with its modern features. In addition to a gas fireplace, each room offers an oversized Jacuzzi and king bed. They even offer a ‘pillow menu,’ including your choice of goose down, organic buckwheat, and bamboo pillows.

Dinner: Friday Harbor House

Friday Harbor House Restaurant

Photo provided by Friday Harbor House

Stay one site. The hotel’s restaurant offers a seasonal menu loaded with fresh, locally sourced ingredients. Not to mention, the marina view is hard to beat.

Small Excursion: Rent a Scoot Coupe

Enjoy an effortless excursion of San Juan Island in a scoot coupe. The adorable 3-wheeled design lets you meander through the island and along the coast. 646-573-2580

Rosario Resort, Orcas Island

Rosario Resort

The old-world elegance of Rosario Resort is hard to beat. Tucked beside Cascade Day, the elegant craftsman style mansion was finished in 1909. It remains richly appointed with elegant woodwork and a 1,972-pipe organ. Throughout the grounds you’ll find a variety of lodging accommodations, most of which offer stunning, waterfront views.

Dinner: The Mansion Restaurant

Rosario Resort dinner

In keeping with the resort’s posh décor, The Mansion Restaurant’s elegant dining room is worthy of dressing up (should you be so inclined). But that doesn’t mean you can’t ‘grab a slice.’ The woodfired oven makes some of the best sourdough crust pizza around, with unique combinations, like razor clams, kale and fried garlic on a lemon cream sauce.

Small Excursion: Tour the Moran Mansion Museum

A tribute to Robert Moran who built the mansion, the Moran Mansion Museum features photographs and artifacts from the early 1900s.

Roche Harbor Resort, San Juan Island

Roche Harbor Resort

Once a lime kiln factory, Roche Harbor Resort is nestled beside a protected marina on the Northern end of San Juan Island. The breathtaking grounds feature manicured gardens, a picturesque chapel and hotel, and multiple dining options. There’s a plethora of accommodations from which to choose, some with fireplaces and some without. But as long as you make it to Lime Kiln Café for a freshly made donut, it really doesn’t matter where you stay.

Dinner: McMillin’s Dining Room

Steak Bites

A fine dining tradition on the island, Roche Harbor Resort’s McMillin Dining Room specializes in 60-day aged Nebraskan prime rib served with house-made horseradish. Also delicious are the tender prime beef bites marinated in Korean barbeque sauce and wok-seared.

Small Excursion: Meander to the Mausoleum

Roughly a mile from the resort you’ll find the Afterglow Vista, the final resting place of the mineral magnate’s family. The beautiful mausoleum features an open-air rotunda with a huge limestone table at its center.

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