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While it’s not the largest island in the San Juans, nor does it have the tallest peaks, San Juan Island is arguably the most popular. Home to the biggest town (downtown Friday Harbor), along with one of the world’s best land-based whale watching destinations (Lime Kiln Lighthouse), this iconic getaway is the perfect place to rest, refresh, and refuel. 

With travel to San Juan Island taking as little as 25 minutes, it’s easy to maximize your time for a quick weekend getaway — a serious boon when there are so many fun things to do. This 48-hour itinerary is a sampling of the best things to do in Friday Harbor and throughout the island. Enjoy.

Friday on San Juan Island

6:30 p.m. Dinner at Cynthia’s Bistro

If you’re in the mood for a specific cuisine or want your plate to look like a work of art, Cynthia’s Bistro probably isn’t for you. But if you’re in the market for good food — the kind of heartwarming meal that’s flavor-forward and seasonally based — this Friday Harbor gem is a sure bet.

Classically trained, Cynthia Burk cooks the kind of food she’d serve dear friends and loved ones. Her spice répétiteur draws from a wide range of regions, while her ingredients are island-infused. 

Saturday on San Juan Island

8 a.m. Rocky Bay Cafe

This quaint little gem has been called “the ideal hometown diner” by Food Network star, Rachel Ray. Ray praised Rocky Bay Cafe’s heart omelets and flavorful biscuits and gravy. But those aren’t the only menu items worthy of note.

The corned beef hash is slow-roasted. The extensive Benny Bar selection ranges from crab cakes to veggies. And the huevos rancheros come with and without chorizo. This is the kind of comfort food that just wraps you up in a hug. 

10:00 a.m. Beach Combing at South Beach

The southern side of San Juan Island is beautifully harsh. What survives on the grassy hillside is hardy, to say the least. Windswept trees bend with the horizon, clinging to the ground. Along South Beach, the rocky coastline is littered with driftwood.

It’s hard to believe American Camp was established in such a harsh climate when further inland temperate grasslands abound. But the strategic advantages are clear. 

For those willing to brave the blow of salty air, stunning views abound. On clear days, the Olympic Mountains stand guard over the Salish Sea. On the southernmost tip of the beach, Cattle Point Lighthouse protects ships from the punishing coast.

11:30 a.m. Lunch at Downriggers

On the eastern side of Front Street, tucked just above the marina, offers a plush mix of modern decor and laidback island life. The generous windows showcase stunning views of seaplanes taxiing and Washington State Ferries motoring into port. 

A menu of small plates (like Dungeness Crab Tots) and heartier entrees (like Spicy Prawn Mac and Cheese) give a seafood-infused update to classic comfort food. 

2 p.m. Shopping in Friday Harbor

Despite its size, Friday Harbor offers a plethora of art galleries and novelty shops. Among the multiple can’t-miss-stops is the which has a contemporary selection of art and jewelry inspired by the Pacific Northwest. 

At the , you’ll find an inspiring range of Aboriginal art. At Printshop Northwest, you can embrace your creative side by designing a one-of-a-kind printed shirt. 

In , you can discover a selection of candles, herbs, and island-inspired gifts. Love finding gently loved books? Don’t miss Serendipity, the island’s quaint used bookshop housed in a historic home.

And for the whale enthusiast, don’t forget to check out the Whale Museum’s gift shop. It’s located right by your next stop. (The museum is also worth a visit! Dedicated to the preservation of the Southern Resident Orcas that frequent the Salish Sea, it also offers educational insights about humpbacks, porpoises, and more!) 

5 p.m. Dinner at The Restaurant at Friday Harbor House

Meander to the ‘other side of town’ (it’s just .3 miles) and you’ll find the . Perched on a small bluff above the marina and the ferry landing, you’ll be treated to a more complete picture of the active waterway. The hotel’s restaurant specializes in refined northwest fare, with menu favorites like a charred corn crab dip and a wild halibut delivering big, bold flavors.  

7:30 p.m. Evening Cocktails at Anchors Away SkyBar

In keeping with the ultimate island getaway, end the evening with another view-filled stop. (also known as the Friday Harbor SkyBar) is a small gem known for its wine flights and knowledgeable staff. The open-air deck features firepits, heaters, and a tent (during the rainy season). 

Sunday on Orcas Island

9:00 a.m. Breakfast at Roche Harbor’s Lime Kiln Cafe

One of the many tasty dining establishments within the island’s famed Roche Harbor Resort, is best known for its famous donuts. The cake-like babies are made fresh daily and available until they sell out (which is often). In addition, the water-front diner offers a hearty selection of American breakfast classics.

10:30 a.m. Hike, Walk & Explore on San Juan Island’s Northern Side

Roche Harbor Resort isn’t just a place to grab a bite. The grounds themselves are a sight to behold. The iconic Hotel de Haro (a 20-room lodging establishment) was built in 1886. It overlooks the resort’s prime garden. Farther along Ruben Memorial Drive, you’ll also find Our Lady of Good Voyage Chapel, a quaint little chapel built in 1892.

Just a short hike will take you to Afterglow Vista, the Romanesque-style mausoleum that serves as the resting place for the McMillin family who founded Roche Harbor. And if you enjoy intriguing artwork, during your stroll you won’t want to miss the The entrance is located just outside the entrance to the resort. The 20-acre park features roughly 150 unique installations by emerging and world-renowned sculptors.

1 p.m. Lunch & Pints at San Juan Island Brewing Co.

Founded by three locals, San Juan Island Brewing Co. offers a town hall vibe that’s become a gathering place for visitors and locals alike. Opened in 2017, it features a lofted interior space that offers a clear view of the brewing operations. 

Their flavor-forward beers feature a regular selection (such as a hearty nitro stout and refreshing Indian pale ale), along with seasonal pours (like a light and crisp de Haro Light Lager). The food menu also doesn’t disappoint, with woodfired pizzas, hearty burgers, and share-worthy appetizers. 

More Fun Things to Do on San Juan Island