American Road Trips
About 100 miles north of Seattle, the San Juan Islands attract road-trippers with their dreamy seascapes and stunning mountain views near the Canadian border. The ferry system accesses just four of the 170 islands, and this itinerary focuses on the two largest — Orcas and San Juan — a route designated a Washington State Scenic Byway. This 1,000-acre archipelago, collectively protected as a national monument, sprawls within Puget Sound’s “banana belt” — a drier, sunnier pocket — making this an adventure you can enjoy anytime of the year, though some restaurants and hotels close during winter.
Day 1: Seattle to Orcas Island (23 miles by ferry, 95 by car)
From Seattle, cruise 80 miles north on Interstate 5 and State Route 20 to Anacortes, where you’ll catch the ferry. But first, stop for a snack and leg-stretching stroll around this charming coastal community.
- How to plan an epic road trip
- Explore Southern Arizona
- Experience California's Highway 1
- South Carolina adventure
- Scenic Hells Canyon in Oregon
- Washington's San Juan Islands
- Michigan coast
- Art in the Hudson Valley
- Unique Southwest hotels
- Road trip quiz
- Money-saving tips
- 8 travel pros' trip ideas
- Travel news and vacation ideas
Fuel up at Adrift, in the compact city center, trying favorites like Dungeness crab cakes and the sesame-ginger stir-fry. Take in downtown’s 160-plus murals of residents, including a local legend: Bigfoot!
When you’re ready to catch the ferry, head 4 miles west on Route 20 to the terminal. Queue up early: The pandemic has disrupted sailings and also stopped service between the San Juans and Canada (Sidney, British Columbia). Weather permitting, spend the 50-minute trip to Orcas Island on deck, scanning for eagles and marine life.
Once you land, drive 8 miles north on Orcas Road to Eastsound, the island’s main town. If your lodging has a kitchen, watch for roadside pop-ups selling goodies such as freshly caught crab, as well as honesty stands with eggs, produce and even grass-fed lamb. (Be honorable and leave the requested amount of money!) Finish stocking up at the foodie-friendly Orcas Island Market in downtown Eastsound.
Where to stay: Rent one of the 21 cabins at the West Beach Resort, which also has tent and RV sites. For an ADA-accessible room, opt for the Rosario Resort & Spa, a 1909 grand dame on the National Register of Historic Places. Check in for two nights.
Day 2: Exploring Orcas (34 miles)
Immerse in the island’s three pillars: art, nature and gourmet grub (that you can savor while wearing a fleece and jeans). Start by heading 13 miles southeast on Olga Road to Obstruction Pass State Park. Here, madrone trees stand sentinel — their leathery evergreen leaves create a striking contrast to paper peels of cinnamon-colored bark. Two miles of hiking trails descend rocky cliffs to one of the island’s rare public beaches. The ocean bathes multicolored pebbles in this lovely and tranquil spot, which also has 10 first-come-first-served campsites.
About a mile outside the park, stop for an especially sweet farm-stand moment at Little Island Chic. A young girl sells bouquets, beer bread mix, small-batch jam and a wide variety of eggs there. Then dive deeper into local creativity at the nearby Orcas Island Artworks, which occupies a 1938 berry processing plant. Expect masterworks from locals, ranging from handmade leather journals to dreamy landscape paintings.
Continue north on Olga Road for 3 miles and catch the afternoon light gilding Mount Baker, a glacier-mantled volcano, from the San Juans’ highest point: 2,409-foot Mount Constitution in Moran State Park. Fish for rainbow trout, swim in one of the five lakes or hike on 38 miles of trails. (The Cascade Falls loop makes for an easy three-quarter-mile ramble.) Tip: Don’t miss the summit’s castle-inspired tower and its lovely new visitor center.
Finish the day with an island pizzeria feted by the James Beard Awards: Hogstone, on Main Street in Eastound (closed for renovations but reopening later this spring). Chef Jay Blackinton, a punk vegan-turned-butcher, earned kudos as a rising star and then a Best Chef Northwest & Pacific semifinalist in 2020. He cranks out innovative hits, especially his surprising-but-sublime white pizza with cheddar, smoked mozzarella and pickled jalapeños.
Where to stay: Settle in for a second night at the place you booked for Day 1.
Day 3: Adventures on Orcas and San Juan Island (8 miles by ferry, 11 miles by car)
Start the day at Eastsound’s Brown Bear Baking on Main Street, where hearth-baked breads are a standout, especially the Mission fig and apricot loaves. Then browse downtown’s boutiques and ceramic galleries — or detour 3.5 miles west to Orcas Island Pottery, the oldest ceramic studio in the Pacific Northwest. In 1945, the founders traded a four-person dishware set for an old trapper’s cabin that they relocated to a coastal bluff fringed by old-growth cedars and Douglas firs. Shopper favorites: vividly glazed dinnerware and sculptures that evoke sea urchins.
Head back to the dock and hop a 20- to 45-minute sailing southwest to Friday Harbor on San Juan Island. When you land, spend some time exploring First Street, just a short walk from the ferry terminal. (Note: The town has some steep hills, so you may want to bring a power wheelchair if you or someone in your party has impaired mobility.)
The Whale Museum spotlights the 74 deeply endangered members of the Southern Resident orca pods. Examine their skeletons and listen to the sounds of the Salish Sea, the inland ocean stretching between Seattle and Vancouver. A listening booth broadcasts the haunting calls of the area’s orcas (both the locals and visiting “transients”). You can also eavesdrop on other sea life you might encounter in the archipelago, including humpbacks, minke whales, porpoises, seals, sea lions and white-sided dolphins.
Also on First Street, stop into Printshop Northwest, selling evocative designs by local artists on everything from T-shirts to tea towels.
For a special splurge at dinner, drive 5 miles northwest (primarily on Roche Harbor Road) to the Duck Soup restaurant. Sit beside the fieldstone fireplace — or the outdoor firepit — and delight in sophisticated Northwest fare. Think scallops with walnut gremolata, and chickpea madras curry with butternut squash and mushrooms. Or stay in Friday Harbor and hit the more moderately priced San Juan Island Brewing Company. Menu standouts include the black-bean burger and Pig War pizza with Italian pork sausage, prosciutto and pepperoni.
Where to stay: For a cozy perch in Friday Harbor, try Bird Rock Hotel, located three blocks from the ferry terminal. This 1891 building has 15 rooms, which range from European-style shared bathrooms to a suite with an outdoor hot tub and gas fireplace. Need ADA accommodations? Turn to Lakedale Resort, located 5 miles northwest of town, primarily on Roche Harbor Road. It has a classic Western log lodge, plus a cottage, cabins, glamping, vintage Airstream trailers and yurts, along with sites for tents and RVs.
Join today and save 43% off the standard annual rate. Get instant access to discounts, programs, services, and the information you need to benefit every area of your life.
Day 4: San Juan Island (45 miles)
Today begins with a history lesson at American Camp in San Juan Island National Historical Park, 6 miles south of Friday Harbor via Cattle Point Road. In 1859, the U.S. and U.K. garrisoned troops there, after a Yank shot a rogue British boar repeatedly marauding his potato patch. Over the next 13 years, the opposing forces became bored enough to start socializing with one another at picnics, parties and horse races. Diplomacy by mediator Kaiser Wilhelm I of Germany finally ended the standoff, with, ultimately, the only casualty being the hog. Start at the visitor center for an introduction to the fascinating, peaceful Pig War. Its new, fully accessible building opens in spring 2022 and will include comprehensive storytelling about the Coast Salish, the Indigenous peoples who have inhabited the archipelago for about 11,000 years. Archaeologists have uncovered traces of their once-thriving prehistoric villages throughout the park and islands.
While at the camp, hike up to 9 miles of trails along prairie-covered bluffs, watching for 18 varieties of raptors. Foxes often part the grass along Pickett’s Lane and gawk back at visitors. Help keep them wild by not feeding them and by staying at least 75 feet away, unless you’re taking pictures from inside a safely parked car.
For lunch, fill up on upscale pub grub (beer bratwurst, garlicky house-made hummus) at the San Juan Island Brewing Company back in Friday Harbor. Then head 10 miles northwest on Roche Harbor Road to the San Juan Islands Sculpture Park, where more than 150 artworks grace 20 acres of gardens and woodlands. Pieces sell — or rotate out after two years on display — so this nonprofit always makes for an exciting stop, even for repeat visitors.
While you’re in this area, don’t miss the nearby John S. McMillin Memorial Mausoleum (also called Afterglow Vista). Amble the unpaved, half-mile forest trail that starts at Roche Harbor’s pioneer-era cemetery, where worn, mossy, hand-carved stones memorialize immigrants claimed by disease, drowning and dynamite explosions in the quarries. The path leads to a forest glade and the dramatic open-air rotunda housing the cremains of the mineral magnate and his family. It feels like stumbling onto the ruins of an ancient Roman temple that was transported to the Pacific Northwest.
Try ending your trip on a high note with the archipelago’s most charismatic critter: the orca. To maybe catch a glimpse, head 10 miles south of the sculpture park via West Side and West Valley roads to Lime Kiln Point State Park, one of the world’s top places to see whales from shore. An easy hike (1.25 miles round trip) leads to the park’s 1919 lighthouse on a rocky cliff, a great vantage point — and the perfect place for a sunset picnic.
Seattle-based freelance writer and photographer Amanda Castleman contributes to Afar, National Geographic and The New York Times. She founded the online academy Write Like a Honey Badger, which teaches storytelling and promotes representation in the media.