Day One – San Juan Island Southern Loop: Lighthouses & Coastal Bluffs
 
Discover the wild, windswept beauty of the island’s southern reaches, from historic lighthouses to one of the best land-based whale watching spots in the world.

Your cycling journey begins with a flight or ferry to Friday Harbor. We’ll meet you upon your arrival at Memorial Park in downtown Friday Harbor. Following a comprehensive orientation and bike fitting to ensure perfect comfort, we’ll set out on quiet backroads, leaving the town bustle behind. We’ll set out from Friday Harbor, heading southeast through rolling farmlands and quiet country lanes. Our first major landmark is Cattle Point Lighthouse, perched on dramatic bluffs at the island’s very tip. Here, you’ll find breathtaking, panoramic views of the Strait of Juan de Fuca and the Olympic Mountains.
 
The journey continues along the serene and scenic west side of the island. We’ll pedal past the tranquil waters of False Bay, a known spot for spotting shorebirds and eagles. The route then leads us to the crown jewel of the day: Lime Kiln Point State Park, famously known as “America’s Best Whale Watching Park.” We’ll take a well-deserved break here, where you can explore the iconic lighthouse, walk the rocky shoreline, and (with luck) witness orcas from the cliffs.
 
The final leg carries us back to Friday Harbor through serene forests and pastoral landscapes, a peaceful end to an unforgettable coastal ride.
 
Distance: 32 miles | Elevation Gain: 1,785 ft.
Meals: Lunch | Stay: Saturn’s Return Farm & Inn

Day Two– San Juan Island North: Harbors, Art & Whales
 
Begin your island adventure with a loop through the historic and artistic heart of San Juan Island, culminating at a world-renowned whale watching spot.

Your cycling journey begins with a delicious farm breakfast at your Farm Stay.
 
The rolling lanes lead us past English Camp and onward to the picturesque Roche Harbor Resort, a historic lime-kiln port. Here, we’ll explore the incredible Westcott Bay Sculpture Park, an outdoor gallery where art harmonizes with nature. Enjoy a leisurely lunch overlooking the colorful, ever-bustling marina.

Refreshed, the afternoon brings a spectacular coastal ride to Reuben Tarte Park where we’ll scan the rocky shores for keep sakes and possible wildlife spotting’s. We’ll voyage across the center of the island on Egg Lake Road, then stray into Friday Harbor for an afternoon ice cream and shopping. The final leg carries you back to across the center of the island through tranquil, forested farmland—a perfect, peaceful end to your first day.

Distance: 32 miles | Elevation Gain: 1,785 ft.
Meals: Breakfast, Lunch | Stay: Saturn’s Return Farm & Inn

Day Three – Lopez Island: The Friendly Isle & Its Hidden Shores
Embrace the slow pace and genuine warmth of Lopez Island, where the iconic “Lopez Wave” from passing drivers is a way of life. Today is a journey through pristine beaches, fragrant farmlands, and ancient forests.

Our day begins with a scenic Washington State Ferry ride, offering panoramic views of the Salish Sea. Upon arrival on “The Friendly Isle,” we begin a rolling loop through a landscape that feels untouched by time.
We’ll first pedal to Spencer Spit State Park, where driftwood-strewn beaches frame stunning views of the snow-capped Cascade Mountains. The route then winds through a patchwork of small, family-run farms before leading us to the wild and beautiful Shark Reef Sanctuary. A short, forested trail here opens onto a rocky bluff where harbor seals can often be seen basking on the rocks below. For lunch, we’ll gather in the charming heart of the island, Lopez Village, where you can choose from several delightful cafes and bakeries. For the Adventurous: An optional extra loop rewards with a ride down to MacKaye Harbor on the serene southern tip, offering quiet roads and expansive water views. In the late afternoon, we’ll regroup for a ferry to Orcas Island, arriving at our new home, the beautiful Outlook Inn in Eastsound.

Distance: 36 miles | Elevation Gain: 2,287 ft.   Meals: Breakfast, Lunch | Stay: Pebble Cove Farm

Day Four – Orcas Island: Peaks, Shores & Forest Loops
Conquer the legendary climb to the San Juans’ highest peak or immerse yourself in the serene coves and waterways of the island’s wild eastern shore. Today is about choosing your own adventure.

We’ll depart Pebble Cove Farm by boat taxi to Doe Bay the idyllic, bohemian retreat. We embark on a beautifully crafted ride showcasing the island’s creative spirit and quiet harbors. Departing Doe Bay, we’ll wind our way along Obstruction Pass Road to a must-see destination: Obstruction Pass State Park. We’ll stroll along a forest path that leads to a scenic cove. Continuing our ride to Buck Bay.

The day’s culinary highlight is a stop at Buck Bay Shellfish Farm, where you can enjoy the freshest, shuck-your-own oysters. We’ll enter the vast, pristine wilderness of Moran State Park, you’ll cycle along the shimmering shore of Cascade Lake beneath a canopy of ancient fir and cedar. For those seeking the ultimate achievement, a steep, rewarding out-and-back climb leads to the 2,400-foot summit of Mount Constitution. Your effort is repaid with 360-degree panoramic views that stretch to Seattle, Vancouver, and the Cascade Range. This is a ride you’ll never forget. We’ll make the summit in the SAG and take in the views. We’ll skirt the scenic Ship Bay with a pitstop at the Historic Museum in Eastsound a perfect place to find a unique, handcrafted souvenir. Our ride will take us up Enchanted Forest Road with a favorite stop at Orcas Island Pottery, this is the oldest pottery studio in the Pacific Northwest. You’ll have time to explore the whimsical grounds and gallery.

From here, Crow Valley Road guides us on a tranquil journey back to Pebble Cove Farm, offering stunning views of the protected Turtleback Mountain Preserve and passing by serene farmsteads.

Distance: 26 miles/ 38 miles | Elevation Gain: 2,904 ft./ 4,500 ft.
Meals: Breakfast, Lunch | Stay: Pebble Cove Farm

Day Five – Shaw Island Excursion
Shaw Island is today’s destination. You’ll cycle to the ferry then take a puddle jump ride the ferry to the smallest ferry accessible island geographically and population wise (only 240 year-round residents). On Shaw Island you will find sandy beaches, quiet roads and a historic general store – but not much else. And that’s just how the small population likes it.

One of the few places to visit – other than the beaches and parks – is the Benedictine monastery. The resident nuns farm the land here and welcome visitors. Indeed, nuns operated the store and ferry terminal here until 2004. The island is small and the riding is leisurely.

You’ll take an afternoon ferry to Friday Harbor to enjoy a lunch at Market Chef then transfer off island via flight or ferry in the afternoon.

Distance: 25 miles | Elevation Gain: 2,222 ft.
Meals: Breakfast, Lunch | Departure Details: Afternoon flight or ferry