While summer boating roots run deep at Roche Harbor, this historic destination also blooms during the shoulder season. The site — a former lime quarry and manufacturing plant in the late 1800s — is now the pinnacle of luxury on San Juan Island. Modern lodging options (along with more modest historic ones), a host of dining establishments, and a plethora of nearby things to do make Roche Harbor the ultimate destination for families, couples, and gal-pal getaways.

From family vacations and romantic getaways to the ultimate girls’ trip, the San Juan Islands offer a backdrop for magical moments. While the remnants of such memories can be lovingly preserved in a half-faced selfie, such pictures are rarely worthy of a Christmas card. What’s more, often key players (ahem mom) remain neatly tucked behind the camera. 

For many, booking a professional photo shoot isn’t high on the priority list when planning a vacation. Where to sleep, eat, and play takes center stage. But for those wise souls who slip in a rendezvous with a photog, the result can be much more powerful than just a great Instagram post. 

Nestled along the inner edge of Orcas Island’s 57-square-mile ‘horseshoe,’ Outlook Inn’s New Leaf Café has long been recognized as a culinary gem. The hotel and eatery can trace their roots back to the late 1800s, when the site was first opened as a general store of sorts. Both the hospitality and the culinary prowess has evolved (thankfully). The island’s jail is no longer located out back and dental services are no longer offered next to bulk staples, like rice and beans.

San Juan Island is magical. Exploring San Juan Island in a Susie’s Mopeds scout coupe is arguably the best one day adventure from Seattle. Fresh air. Unparalleled views. This is the kind of Seattle to Friday Harbor trip you’ll consider extending.