Day One: San Juan Island: Harbors, Art, & Whales

Visit Roche Harbor, Westcott Bay Sculpture Park, English Camp, & Krystal Acres Alpaca Farm.

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.

Today’s ride crosses the center of the island riding past Beaverton Marsh and Egg Lake on the back roads to the picturesque Roche Harbor Resort, a historic lime-kiln port where history emerges at a slower pace. Here, we’ll explore the incredible Westcott Bay Sculpture Park where you’ll be transformed into fields of masterpieces, 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 Lime Kiln Point State Park. As you cycle south, keep an eye on the sparkling waters—this is prime orca territory! We’ll stop at the park to explore the iconic lighthouse and scan the horizon for the tell-tale spouts of these magnificent creatures. The final leg carries you back to Friday Harbor through tranquil, forested farmland—a perfect, peaceful end to your first day.

The ride follows rolling back roads to Roche Harbor. This sheltered cove has been a haven for sailors for over 150 years. There are several waterfront restaurants – ideal for a leisurely lunch in the sunshine. After lunch, you go on to explore British Camp (the site used by the British troops during the joint military occupation of the Island in 1859).

Distance: 36 miles | Elevation Gain: 2,287 ft.   Meals: Breakfast, Lunch | Stay: Island Inn 123 West

Day Two: Lopez Island ‘The Friendly Isle & Its Hidden Shores’

Lopez Island is the most friendly, peaceful, and relaxed island in the San Juan chain

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. 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. We’ll pass Jones Bay and have views of Davis Bay while 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.

Distance: 36 miles | Elevation Gain: 2,287 ft.   Meals: Breakfast, Lunch | Stay: Island Inn 123 West

Day Three: San Juan Island Southern Loop: Lighthouses & Coastal Bluffs

Whales, Local Treasures from Art to Wildlife

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.

After breakfast, your guide will meet you at the hotel to preview the day’s route. 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: Breakfast, Lunch | Stay: Island Inn 123 West

We start the day with a van transfer to Friday Harbor where we will enjoy a delicious breakfast at the Restaurant at Friday Harbor House. From here, we board embark on a marine wildlife cruise, followed by a delightful lunch near Friday Harbor with time to explore the shops. The hike to the top of Young Hill, where you’ll be rewarded with breathtaking views of the islands. Our day is focused on exploration and discovery of island treasures.

Day Four: Shaw Island Excursion – Transfer Day

Shaw Island is today’s morning destination. You’ll 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 Orcas Island then transfer to Deer Harbor to enjoy a picnic lunch and an afternoon sea kayaking tour to see a variety of wildlife around the Wasp Islands.

Overnight Town: Eastsound is a charming seaside town and artist community. The laid- back atmosphere here can make even Friday Harbor seem hectic by comparison. That said, the clutch of galleries and stores are enough to while away a pleasant couple of hours. Eastsound also has the best ice cream in the San Juans.

Distance: 25 miles | Elevation Gain: 2,222 ft.
Meals: Breakfast, Lunch | Stay: The Village Inn at Eastsound

Day Five: 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.
From Eastsound, our route heads south, skirting the scenic Ship Bay. We’ll enter the vast, pristine wilderness of Moran State Park, cycling along the shimmering shore of Cascade Lake beneath a canopy of ancient fir and cedar.

Choose Your Journey:
The Epic Challenge – Summit Mount Constitution:
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.

The Coastal Explorer – Loops & Bays:
Prefer to keep the wheels spinning? The main route continues to the idyllic, bohemian retreat of Doe Bay, before a beautiful out-and-back ride down Obstruction Pass Road to a secluded, pebbly beach. The day’s culinary highlight is a stop at Buck Bay Shellfish Farm, where you can enjoy the freshest, shuck-your-own oysters.

Day Six: Orcas Island West: Ride Through Art & Harbor

Enjoy a shorter, loop through the artistic and pastoral heart of Orcas Island, offering a final taste of its magic before your journey home.

On our final morning, we embark on a beautifully crafted ride showcasing the island’s creative spirit and quiet harbors. Departing Eastsound, we’ll wind our way along the aptly named Enchanted Forest Road to a must-see destination: Orcas Island Pottery. Nestled on a dramatic, forested bluff, this is the oldest pottery studio in the Pacific Northwest. You’ll have time to explore the whimsical grounds and gallery, a perfect place to find a unique, handcrafted souvenir.
 
From here, Crow Valley Road guides us on a tranquil journey across the island, offering stunning views of the protected Turtleback Mountain Preserve and passing by serene farmsteads. The route culminates at the picturesque Deer Harbor, a classic Pacific Northwest cove with a sandy beach and a charming dock. This is the ideal spot for a final picnic lunch, or you can grab a famous slice at Island Pie.
 
In the afternoon, we’ll take a scenic ferry transfer back to San Juan Island, where your tour officially concludes. For those extending their stay, the enchanting Vancouver Island awaits.
 
Distance: 18 miles | Elevation Gain: 1,936 ft.
Meals: Breakfast, Lunch | Stay: The Village Inn at Eastsound