Each of the islands of Orcas, Lopez and San Juan (San Juan Islands) 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. Starting from the historic village of La Conner, we enjoy an easy day of cycling in the Skagit Valley before cruising to the islands from Anacortes; on the San Juan Islands, there are a few rewarding hills each day but the distances are modest and support never far if needed. In addition to cycling, there is the opportunity to hike to outstanding viewpoints, and sea-kayak in secluded coves. There is even the opportunity to sail for ½ day aboard a historic wooden 42’ yacht. The accommodations are lovely and by week’s end, you won’t want to leave this enchanting corner of Washington State.

Only Great Explorations:

  • Small groups, extraordinary guides, and authentic experiences
  • A view you will never forget: from atop Mount Constitution
  • Order off the menu at restaurants you won’t find in guidebooks
  • We design and operate our own trips so there are only good surprises!


La Conner

La Conner, WA, USA

Day 1

Orcas Island

Orcas Island, Washington, USA

Day 2+3

San Juan Island

San Juan Island, Washington, USA

Day 4+5+7

Lopez Island

Lopez Island, Washington, USA

Day 6

What’s Included in the Cost of Your Trip?


Services of one or more experienced Great Explorations guide(s)
Support vehicle
6 nights lodging
All breakfasts, 2 lunches, and all dinners but 1
Entrance fees for selected historical sites and museums
All ferries and transfers
Detailed maps & GPS instructions
All baggage transportation

Not Included

Bike rental




Jun 22-28
Jul 6-12
Jul 13-19


Jun 23-29
Jul 7-13
Jul 14-20

Trip can start any date. Call or email for details.


4-16 participants


7 days / 6 nights


La Conner / Friday Harbor


Van supported


Moderate with hills, some find rewarding, others find ‘pesky’


Land Cost:
US $3,250 pp
Includes 6B/2L/5D

Single Supplement:
US $820

Bike Rental:
US $280

E-Bike Rental:
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.  

Optional activities:
Sea kayak, SUP rentals are optional activities and can be paid for at rental location.

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 our trips outside Canada are quoted in U.S. Dollars (USD) but we gladly accept payment in Canadian dollars (CAD) also.
If you have any questions or would like to confirm space on this trip before making your reservation, please contact us at info@great-explorations.com or by telephone at 604 730 1247 | +1 800 242 1825.

Getting there
Our trip starts near Fidalgo Island, in the village of La Conner, which you can reach by private transfer or Bellair Shuttle from Seattle. We meet at 12:30 pm and over a picnic lunch make introductions and prepare you for the week ahead. If you have arrived by the Bellair Airport Shuttle, we can pick you up instead at 12:15 at the La Conner Whitney Shell Station, where the shuttle drops off.


Day 1

La Conner, Washington

We will enjoy an easy-going (translated flat) ride today in the Skagit Valley, which is surrounded by the Salish Sea and farmland filled with tulip and daffodil bulbs. The town of La Conner has been described as a tiny town with big charm. Many of the buildings are historic and a visit to the museum will reveal an interesting past for the town. We will enjoy a welcome wine reception at the hotel and then enjoy dinner at the Oyster & Thistle Restaurant. The Channel Lodge is on the waterfront and is a comfortable and charming inn.

Ride distance: 17mi (30km); elevation gain 120’ (50m).


Day 2

Anacortes to Orcas Island

We start the day cycling from La Conner to Fidalgo Island and on to Anacortes, where we board a ferry for the one hour cruise to Orcas Island. Your destination is the village of Eastsound, and the Outlook Inn. The village has a vibrant atmosphere, full of shops and galleries. We will visit the Orcas Island Historical Museum before dinner at the hotel’s New Leaf Café. 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 a 43 acre estate on the island.

Ride distance: 26mi (43km); elevation gain 900’ (300m).


Day 3

Orcas Island

Today, we ride to Moran State Park. You can decide how to explore this 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 Archipelago. In Olga, visit Orcas Island Artworks, where you can visit Orcas Island artisans in pottery, jewelry, glass, wood, metal, paintings, & wearable art. If you are riding the longer option, lunch at Doe Bay is recommended or alternatively stop for a picnic lunch at Cascade lake on the return; there is a lovely lakeside trail to enjoy or, take a swim if you choose. Back in Eastsound, we will dine at one of our favorite restaurants there for a fun evening.

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


Day 4

San Juan Island

We ride south on this day, stopping to visit a local potter and later a winery to taste on the way to Deer Harbor, the largest marina on Orcas. Stop and enjoy a refreshing drink overlooking the harbor and then continue along to the village of Orcas, where lunch awaits. We then ferry to Friday Harbor on San Juan island, our next destination. Friday Harbor is charming, historic and pedestrian friendly with plenty of eclectic restaurants and cafes. Stroll through town and check out the Whale Museum, the San Juan Islands Museum of Art or the San Juan Community Theatre for musical events. If you are interested in a sun-set paddle, this is an option. On this evening, you can enjoy dinner on your own and the guides will provide recommendations.

Ride Distance: 20mi (32km); elevation gain 1,400’ (490m).


Day 5

San Juan Island

Today, we’ll 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 and enjoy the rest of the afternoon there.

Ride Distance: 28mi (46km); elevation gain 1,800’ (600m).


Day 6

Lopez Island

Cruise from Friday Harbor to Lopez Island, where we’ll cycle a loop to Lopez Village and the most scenic part of the island on quiet roads. The cycling on Lopez is easier/less hilly than San Juan or Orcas Islands, so you’ll enjoy gliding around effortlessly. Return to San Juan Island to enjoy your final night at Friday Harbor with a wine reception and dinner.


Day 7

Departure Day

There may be time for a last morning spin. Fly out by sea-plane from either Friday Harbor or Fisherman’s Bay to Seattle at 10am. What a way to finish your trip!

Channel Lodge, La Conner

This rustic-chic cedar-shake sided property overlooks Swinomish Channel with comfortable guest rooms with gas fireplaces and private balconies. There is a luxe spa on site and a pub style restaurant, the Oyster & Thistle Restaurant.
Alt: La Conner Country Inn

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.
Alt: Inn at Ship Bay

Friday Harbor House, 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.
Alt: Tucker House Inn


Trip Reviews

September 18, 2021

“I write in appreciation of all your flexibility and skill in arranging our fabulous San Juan trip. Frankly, the decision to ask you to arrange the trip was motivated by COVID-19 challenges to going to places perceived as more exotic. In short, visiting the San Juan’s was a default destination trip. Now, our gratitude for our San Juan experience is beyond profound. We adapted to the e bikes you secured. That opened doors to challenging terrain of ethereal beauty. And the full day sail with Captains David and Barbara and baby Skye will always be a treasured memory. And, I know we have preciously relayed our appreciation of our tour guide but what other travel company could recruit a former submarine commander to lead a biking tour? He set a high bar for his intelligence, energy and adaptability. He made us feel like guests rather than professional obligations. I truly wish you many more years of introducing folks to new worlds.”

July 8, 2021

‘Fabulous trip. We had an excellent guide: knowledgeable, considerate, attentive to details and fun. We enjoyed the personalized trip planning and emphasis on both fun and history. Guides are excellent at making the trip unforgettable with serendipitous experiences, careful attention to every detail, service and just plain kindness. The kayak tour, lavender farm, pottery shop, wine tasting and Duck Soup restaurant were all fabulous. Love the GPS Bike App. Excellent ride options and our guide was flexible. Interactions with the Travel Advisor exceeded our expectations.’

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