Each of the islands of Orcas, Lopez and San Juan offer abundant options for cycling, enchanting hikes, superb beaches and unique marine ecosystems. This is the best of the Pacific Northwest, world’s away from mainland, where the island charm is welcoming. Your trip starts from Friday Harbor, on San Juan Island, easily reached by ferry from Anacortes, or by sea-plane from Seattle. This region is a paradise of natural splendor with winding roads through verdant forests and along sublime coastline. Spot whales from the shores of Orcas Island, enjoy farm-to-table dining by burgeoning chefs.  In addition to cycling, there is the opportunity to hike to outstanding viewpoints, and sea-kayak in secluded coves. The accommodations are lovely and by week’s end, you won’t want to leave this enchanting corner of Washington State.


San Juan Island

Friday Harbor, WA, USA

Day 1+2

Lopez Island

Lopez Island, Washington, USA

Day 3+4

Orcas Island

Eastsound, WA, USA

Day 5+6+7

What’s Included in the Cost of Your Trip?


6 nights lodging
All breakfasts and 1 dinner
Luggage transfers (you are responsible for your luggage onto the ferry from San Juan to Orcas)
Detailed GPS instructions and maps
Personal meet & greet with our local Area Manager
Area Manager available throughout the tour

Not Included

Ferry fares



You can start any date between June 1 and September 30.
Saturday is market day in Friday Harbor, San Juan Island & in Eastsound, Orcas. Custom trips also available and can start any day. Call or email for details.


7 days / 6 nights with 6 days biking


Friday Harbor, San Juan Island / Eastsound, Orcas Island




Moderate with hills, some steeper grades


Classic Accommodation: US $2,450
Single supplement: US $620

Luxe Accommodation: US $2,950
Single supplement: US $745

Bike Rentals

Hybrid or Racing Bikes: US$280

E-Bikes: US$480

E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.  

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services. Due to the nature of our business and exchange rates, prices are subject to change. All prices quoted are U.S. dollars but we gladly accept payment in Canadian dollars also. If you have any questions before making your reservation, please contact us.
Getting There The trip starts from Friday Harbor which you can reach by seaplane from Seattle or via the high-speed San Juan Clipper departing from Pier 69. Alternatively, you can reach Friday Harbor by ferry from Anacortes. Note re. ferries: The inter-island ferries between San Juan Island and Lopez Island and Orcas Island are free for walk-on passengers and cyclists.


Day 1

San Juan Island

Arrive to Friday Harbor, San Juan Island. Meet your bike(s) and get an orientation for your trip. Enjoy a leisurely first-day’s ride around Pear Point stopping by a farm stand that sells organic berries, vegetables, flowers. Pass Jackson Beach, a long sandy beach just 2 miles from town. Back in Friday Harbor, enjoy the first of many wonderful dinners – the first one is on us.

Ride distance: 6mi (10km); elevation gain 100’ (30m) or 12mi (19km); gain 600’ (200m).


Day 2

San Juan Island

Options today include an easy-going loop to False Bay, where newly paved road skirts the San Juan Marine Islands Marine Preserve. Or ride south to Lime State Park, which boasts the only whale watching park in the USA. Orca sightings are possible here from the waterfront. Continuing on to Roche Harbor, there is an opportunity to sea-kayak in the quiet bays there. Should you not wish to sea-kayak, you can ride back to Friday Harbor, wine tasting en-route, and enjoy the rest of the afternoon exploring more of the village.

Ride distance: 12mi (19km); elevation gain 600’ (200m) or 21mi (34km); gain 1,440’ (480m) or 28mi (46km); gain 1,800’ (600m).
Sea-kayaking option.


Day 3

Lopez Island

After a leisurely breakfast, enjoy another morning ride and then take the ferry to Lopez, the flattest and least populated of the three islands of the archipelago. You will make your way to the village of laid-back Lopez and the lovely Edenwild Boutique Inn. Ride part (or all) of the Tour de Lopez, a popular local event that brings cyclists to the island.

Ride distance: up to 36mi (60km); elevation gain 2,400’ (800m).


Day 4

Lopez Island

We provide lots of options today from more cycling, to hikes or sea-kayaking. The hiking options include Shark Reef Santuary, a 39-acre sanctuary that boasts verdant forest carpeted in salal with trails that lead to beaches teeming with wildlife – eagles, cormorants, kingfishers and oystercatchers dining on seafood and seals basking on the warm rocks. If golf is your thing, you can even do this – the 9-hole course rarely has a wait. Whatever you decide, the day is yours. The island prides itself on their not bring stoplights, mopeds, or shopping malls. That’s our kind of island!


Day 5

Orcas Island

Today, you’ll ferry to Orcas Island. There are a few different routes up the island – you can decide whether you want the direct, flatter route or (our preferred) route that is more interesting and quieter but with a bit of a climb on the way. Your destination is the village of Eastsound which has a vibrant atmosphere, full of shops and galleries. Visit the Orcas Island Historical Museum before dinner at the New Leaf Café, a superb dinner option in town. Orcas Island made the travel list of NY Times in 2019 as one of the top 52 Places to Travel to. The article waxed poetic about the tide-to-table culinary scene and experimental wines, attracting among others, Oprah Winfrey, who recently purchased an estate on the island. Farmers, fishermen, artists, retirees and summer-home owners make up the population of about 4,000 residents.

Ride distance: 15mi (25km); elevation gain 1,350’ (450m).


Day 6

Orcas Island

Today, ride to Moran State Park. Hike up a lovely trail or challenge yourself on the steeply paved road to the top of Mt Constitution, the highest point in the San Juan Islands. From a tower constructed by the Civilian Conservation Corps, enjoy a 360 degree view including Mount Baker, the North Cascades, and other islands of the San Juan Archipelego. In Olga, stop in at Orcas Island Artworks, where you can visit artisans in pottery, jewelry, glass, wood, metal, paintings, & wearable art. Lunch options include a café at Doe Bay or stop at the Buck Bay Oyster Farm and learn to shuck and taste fresh oysters. On the return trip, stop at Cascade lake; there is a lovely lakeside trail to enjoy or, take a swim if you choose. Back in Eastsound, enjoy cocktails before dinner at our favorite local eatery.

Ride distance: 13mi (22.4km); elevation gain 1,320’ (440m) or 21mi (34km); gain 1,800’ (900m) or 25mi (40km); gain 2,520’ (840m).


Day 7

Departure Day

You can fly out of Eastsound, Orcas Island Airport to Seattle/Boeing Field (dep typically 8am & 10:20am and takes 40 min; cost is approximately $169).



Tucker House Inn, Friday Harbor, San Juan Island

Several 19th and 20th century homes and cottages comprise this inn, and the 18 guest rooms feature balconies or fireplaces. Kayaks are free to use here.
Alt: Earthbox Inn & Spa

Edenwild Boutique Inn, Lopez, Lopez Island

This venerable inn has quaint, individually decorated guest rooms with handcrafted furnishings, some with water views. There is a common living area, patio and gardens.

Inn at Ship Bay, Eastsound, Orcas Island

Located 1 mile from Eastsound Village, this oceanfront hotel was built around the historic 1869 Adam’s farmhouse in the center of heirloom plum, pear and apple orchards. The restaurant showcases organic products, most of which come from on site kitchen gardens.


Friday Harbor House, Friday Harbor, San Juan Island

On a bluff overlooking Friday Harbor, this sophisticated retreat boasts chic rooms with harbor, mountain, or island views. A bright, airy restaurant and bar has a grassy terrace and harbor views.

Edenwild Boutique Inn (Classic), Lopez, Lopez Island

This venerable inn has quaint, individually decorated guest rooms with handcrafted furnishings, some with water views. There is a common living area, patio and gardens.

Outlook Inn, Eastsound, Orcas Island

This hotel’s original building is from 1888 but the real buzz is about the new luxury suites recently added. The hotel overlooks Fishing Bay and is close enough to Moran State Park to bike to.

Trip starting at
USD $2,450

Trip Reviews

October 31, 2023

“Always heard that San Juan Islands was a dream destination for cycling. We found it was that and more – beautiful scenery, delicious food, wonderful inns/hotels, kind people-truly perfect. The trip was truly a fairytale. The riding was perfect, the transfers all worked out, and having the proposed routes, the accommodations booked, and the support of Randonnee along the way, while still traveling on our own, was the perfect combination. Riding along little traveled roads with sun dappling through the pine trees, spotting humpback whales off San Juan Island, seeing snow-capped peaks in the distance, relishing the late summer light and sunsets, savoring incredible sea- and farm-to-table restaurants, the whole week was memorable, restorative, and a celebration of all that we love. Our Travel Advisor was especially helpful as we prepped for the trip. Our Area Manager shared a helpful overview, route notes, and logistics and was responsive via text during our trip.”

September 20, 2021

“We had a great trip. The San Juan Islands are beautiful and it was a joy experiencing the islands for the first time. We took the sea plane ride to get there and It was so much fun! It’s great having destinations along the way adding to the adventure. Wild Island is a gem. The Deer Harbour loop was a gorgeous ride, out of a picture book and Enchanted Forest Road was magical including riding into Orcas Island Pottery, what I call ‘Pottery Gardens’. Lovely. Thank you for coordinating our memorable trip!”

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