The San Juan Islands are an understandably popular summer destination for travelers from all over the world, but those of us who live in the North Sound are lucky to have year-round access to their beauty. And I’d argue that the low season—late fall through late spring—is actually the best time to visit. Especially if you, like me, are the kind of traveler who prioritizes food and views above all else.
If you’re itching to get away for a little romance and indulgence this month, why not hop a ferry to Orcas or San Juan Island? Book a luxurious room for low-season rates, spend the morning watching the water from a cozy spot by the fire, pop out for a chilly walk around the less-crowded downtown, warm up with a perfect bowl of chowder or plate of pasta, then repeat…honestly, what could be better?
Eastsound, Orcas Island
STAY: Outlook Inn
Originally built in 1888, the building at the core of this rambling waterfront property in Eastsound began its life as a town hub, containing a general store, post office, and even a jail. The second owner was the one who expanded the building and turned it into a 22-room hotel, and over 100 years (and a few owners) later, Outlook Inn boasts 32 luxurious rooms, including the five incredible Water’s Edge suites. Built in 2019 across the street from the rest of the hotel, the suites sit right on the water, with balconies that seem to hover over the waves at high tide.
Photograph by Anne Godenham
While the water views are clearly a major draw, there’s something to recommend to every room on the property; even the few rooms that don’t face the water offer updated amenities and luxuries like organic toiletries, in-room Nespresso machines, and plush robes.
EAT
Eastsound’s downtown area is tiny, but the restaurant saturation is high and the caliber of food is excellent. From bakeries to lunch spots to fancy dinners, you can find it all.
Photograph by Anne Godenham
A pastry from Brown Bear Baking is the best way to start your day, especially if you supplement it with a coffee from Bookstore Coffee Co. just across the street (inside Darvill’s Bookstore). For authentic Mexican dishes served in a cozy, homey space, you can’t beat Mijitas—the house specials Lomo de Puerco and Pollo al Carbon are both exceptionally flavorful and tender. If you’re craving pizza, grab a slice or take a whole pie to go from Ladybug Pizza, where the pepperoni pizza is topped with those tiny cupped pepperonis (always a sign of quality in my mind) and the crust is perfectly blistered and chewy. And if you’re celebrating or just love a high-end tasting menu, try Matia Kitchen (check out our April 2024 review, written by Kristen Boehm, for more details!).
Friday Harbor, San Juan Island
STAY: Friday Harbor House
Friday Harbor is bigger and more populous than Eastsound, but Friday Harbor House offers a similar level of peaceful retreat, with all 24 rooms including a gas fireplace, king bed, and jetted tub with space for two—and, of course, many offer exceptional views of the harbor. Our room included a sweeping corner view, sliding floor-to ceiling doors, and even a small balcony! It was an incredible place to wake up; drinking my coffee in my robe every morning, overlooking the harbor’s comings and goings, felt almost as relaxing as a massage.
Photograph by Anne Godenham
EAT
Open year-round, The Restaurant at Friday Harbor House serves up contemporary American cuisine with a focus on seasonality and thoughtful sourcing. It’s a great place for an intimate dinner—especially because there’s no drive home, so you can indulge in a cocktail or two! Jima Sushi and Downriggers are great spots for a casual lunch or dinner, and if you just want to huddle by the fire in your robe Vic’s Drive In has you covered with take-out diner food, including milkshakes and floats. Fancy getting dressed and taking a drive? Make a tasting appointment at San Juan Vineyard, then head to Duck Soup for an indulgent, locally sourced dinner (read more about it in our September 2022 review).
Photograph by Anne Godenham
If you’re a coffee addict like me, you’ll want to know where to get your fix. For a ‘walking around’ latte, Crows Nest Coffee Shoppe and Sweet Retreat & Espresso are both perfect for a grab and go. If you want to sit a spell, Salty Fox Coffee has a generous indoor space and delicious all-day breakfast options.
While some activities and restaurants on the islands do close during the winter, there’s still plenty to do—and, perhaps more importantly, eat! —in the low season. So why not brighten the dark, cold days with a weekend away?
Photograph by Anne Godenham
(Note: if you’d rather wait and plan a visit for the fall, San Juan Island Restaurant Week is a new annual event that will return for its second year in November 2025!)
