Meet your guides at our first hotel in the quaint seaside town of Friday Harbor. We’ll kick things off with a picnic lunch overlooking Puget Sound, followed by a bike fitting and safety review. Then it’s time for our first fantastic ride: take a spin around Pear Point and pass driftwood-strewn Jackson Beach. Head back to the hotel or opt for some extra miles before tonight’s welcome cocktail and harbor view dinner.

Accomplished: 26 miles / 42 km, elevation gain: 1,643 feet / 501 meters

Longer Option: 50 miles / 80 km, elevation gain: 3,175 feet / 968 meters

Today’s loop ride covers nearly every road on San Juan Island! At Westcott Bay, we’ll stop to learn about the aquaculture of oysters and shuck our own shellfish for a decadent lunch. Afterward, cycle back to Friday Harbor and take a stroll down the docks or peruse the town’s boutiques. Tonight we invite you to dine on your own at one of Friday Harbor’s many charming restaurants.

Accomplished: 35 miles / 56 km, elevation gain: 2,995 feet / 913 meters

Longer Option: 59 miles / 95 km, elevation gain: 4,769 feet / 1,454 meters

This morning we move on from San Juan Island and make our way to Lopez Island. With 63 miles of shoreline and just 2,500 year-round residents, this 15-mile landmass is known as the “Friendly Isle.” We’ll cover most of it on a loop ride through forests and rolling farmlands with quiet bays and beaches in our midst; our route follows the annual Tour de Lopez, a celebrated event for local cyclists. We’ll pause for a picnic-style lunch, then visit a glassblower’s workshop to discover artisans at work on the island. This afternoon, hop a ferry to Orcas Island—our last stop in the San Juans. Ride your bike right off the ferry or hop in the van and head directly to our next hotel, which occupies a private bay at the foot of Mount Constitution. This evening, we’ll enjoy an early dinner before an unforgettable sunset cruise.

Accomplished: 37 miles / 59 km, elevation gain: 2,490 feet / 759 meters

Longer Option: 51 miles / 82 km, elevation gain: 4,070 feet / 1,241 meters

Ready for some climbing? Start with a warmup ride to grab a coffee in nearby Eastsound, then tackle the climb to the top of Mount Constitution, the highest point in the San Juan Islands—on a clear day, you can see all the way to Mount Rainier and the cities of Vancouver and Victoria in British Columbia. Not up for a climb today? Get a lift to the top then enjoy the descent, whizzing by remote harbors all the way down to Doe Bay. After lunch, choose to bike back to our hotel or paddle a kayak across Doe Bay, a hotbed for local marine life. Explore historic Eastsound on your own tonight—it lends itself well to gallery-hopping before dinner.

Accomplished: 27 miles / 43 km, elevation gain: 3,693 feet / 1,126 meters

Longer Option: 35 miles / 56 km, elevation gain: 4,694 feet / 1,431 meters

This morning we’ll take our leave of Orcas and ride the length of both Fildago and Whidbey Islands. This route is known to participants of the Century Ride, an annual event that cycles Whidbey’s pine forests and farmlands with exceptional views of Puget Sound. We’ll cross Deception Pass, an iconic strait with a fascinating history, and pedal into sleepy Coupeville for lunch at a local café. In the afternoon, you can catch a ride in the van or bike the remaining 37 miles of Pacific Northwest beauty. We’ll spend our last night in the picturesque town of Langley, gathering for a farewell cocktail before dinner at the hotel’s intimate restaurant.

Accomplished: 37 miles/ 59 km, elevation gain: 2,729 feet / 832 meters

Longer Option: 69 miles / 111 km, elevation gain: 5,018 feet / 1,530 meters

Say goodbye to Langley with a leisurely breakfast or take the opportunity for one last early morning ride. Your guides will transfer you back to downtown Seattle

. Accomplished: 18 miles / 29 km, elevation gain: 1,345 feet / 410 meters