Cycling the San Juan Islands

Cycling the San Juan Islands

Visit Washington State's San Juan Islands, riding some of the quietest and scenic terrain available in this spectacular state. Slow down and take it all in - a temperate climate, tranquil waters, mountain vistas, and the chance to get glimpses of whales – elements that are sure to make your island-hopping-by-bike experience truly unique. Our San Juan Islands Bike Tour is one of a kind.

This trip is designed as a loop so you can drive to and from the tour in case you prefer not to fly. Save $200 if you decide to bring your own bike.

Dates: Pick a date below or select your own date, starting on a Sunday. We are able to operate this tour with 4 or more people. Price changes may apply for 4 people. Given the unique circumstances surrounding travel we understand if you are more comfortable traveling in a private group.

There are no upcoming tours scheduled at this time.

Tour Style: Classic Hold-A-Space/Questions Request Custom Date Download Itinerary Tour Map
  • Trip At-A-Glance
  • Tour Summary
  • Daily Itinerary
  • Travel Information
  • Map
  • Reviews
Trip At-A-Glance

Trip At-A-Glance

  • Length / 6 Days
  • Total Distance / 153 miles (248 km)
  • Avg. Distance / 26 miles (41 km) per riding day
  • Tour Level & Tour Style / 3.0 Classic
  • Countries / USA
  • Begin/End / Anacortes, WA
  • Price / From USD$3575
Tour Summary

Tour Summary

  • Highlights
    Anacortes; Friday Harbor; Whale Watching Cruise; Lavender Fields; Orcas Island; Cycling Mount Constitution; Doe Bay
  • Includes
    6 days, 5 nights lodging, double occupancy; meals as noted in itinerary; non-optional activities as outlined in itinerary; ride-friendly snacks and beverages throughout each day; hybrid or alloy road bike rental – carbon road bike or E-bike available for an upgrade fee ($100 for carbon; $200-300 for e-bike); professional trip leader(s); van support & porterage service; reusable water bottle & luggage tags.

    Learn more about what is included and what to expect on your Classic tour at the Classic Tour Style page.
  • Arrive / Depart
    Seattle's Sea-Tac Airport (SEA)
  • Overall Tour Level
    3.0 difficulty level 3.0

    Level to Very Hilly, options for longer or shorter rides

  • Daily Ride Summary




    Day Level


    34km / 518m
    Rolling hills
    difficulty level 2.0
    66km / 884m
    Rolling hills
    difficulty level 3.0
    29km / 366m
    Rolling hills
    difficulty level 2.0
    48km / 793m
    difficulty level 3.0
    Hike option
    35km / 701m
    difficulty level 3.0

Terrain Legend

Gentle Gentle

Rolling hills Rolling hills

Hilly Hilly

Very hilly Very hilly

Mountainous Mountainous

Daily Itinerary
Download Itinerary

DAY 1: Meet in Anacortes, Bike Fidalgo Island Loop

Highlights: Anacortes, Fidalgo Island

After meeting in Anacortes, WA (~1 pm, about 90-min drive north from Seattle) for a brief orientation we’ll pedal around Fidalgo Island taking in stunning water views of the surrounding Puget Sound. After getting settled in for our lodging for the evening we’ll enjoy the first of our meals together.

  • Distance: 34km (21mi)
  • Gain: 518m (1700ft)
  • Terrain: Rolling hills
  • Day Level: difficulty level 2.0
  • Meals: Dinner
  • Lodging:

DAY 2: Anacortes to Friday Harbor

Highlights: Bike San Juan Island Loop

After breakfast we’ll board the first of the ferries we’ll take this week traveling among the San Juan Islands to the town of Friday Harbor. Upon arrival we’ll loop around the entire island – which in the middle of the 19th century was subject to a border dispute and was once divided between the UK and the USA, as both claimed it as their territory. Fortunately, despite the presence of troops from each country, the only fatality was a pig, hence the incident was dubbed the “Pig War”. You’ll have options to stop along the way to learn more about this quirky chapter in American history as we pass by the American and English camps that comprise San Juan Island National Historical Park.

September: Possible Upgrade Option - Tucker House Inn

  • Distance: 66km (41mi)
  • Gain: 884m (2900ft)
  • Terrain: Rolling hills
  • Day Level: difficulty level 3.0
  • Meals: Breakfast, Lunch, Dinner

DAY 3: Friday Harbor - Whale Watch

Highlights: Whale watching cruise, Lavender Farm Loop

Today we’ll return to our bikes for a morning ride looping inland on the island past a lavender farm before returning to Friday Harbor. After lunch on your own in Friday Harbor, we’ll board a whale watching boat and, with luck, have the opportunity to see Orca whales in the wild. Our boat ride is 3-4 hours and if whales aren’t featured we may see other wildlife including bald eagles. Tonight we enjoy another great dinner in Friday Harbor with ample fresh, local seafood options if you are so inclined.

September: Possible Upgrade Option - Tucker House Inn

  • Distance: 29km (18mi)
  • Gain: 366m (1200ft)
  • Terrain: Rolling hills
  • Day Level: difficulty level 2.0
  • Meals: Breakfast, Dinner

DAY 4: Friday Harbor to Orcas Island

Highlights: Orcas Island, pottery studio

This morning we take another ferry to Orcas Island. You’ll pedal off the boat from there stopping at Deer Harbor then a pottery studio featuring the work of several local artists and a stunning natural setting overlooking the Canadian Gulf Islands just across the border a few miles away. After a guide-prepared picnic lunch you’ll pedal onward to our home for the next two nights in Eastsound. You are free to explore and choose your own dinner restaurant tonight.

September Hotel: Outlook Inn

  • Distance: 48km (30mi)
  • Gain: 793m (2600ft)
  • Terrain: Hilly
  • Day Level: difficulty level 3.0
  • Meals: Breakfast, Lunch

DAY 5: Hike Orcas Island

Highlights: Explore Orcas Island

You'll have the option to hike today, including the possibility to hike Mt Constitution. At 2,398 feet, it’s the tallest point in the San Juan Islands and features a stunning panoramic view of the surrounding islands in the US and Canada as well as Washington’s snow-covered Mt Baker rising over 10,000 ft. After returning to Eastsound, you'll have time to shower before check out. We’ll return by ferry to Anacortes (arriving ~ 2pm – dependent on ferry schedule and ferries sometimes run late) where we will say goodbye and you can continue your adventure as you please!

  • Meals: Breakfast, Dinner

DAY 6: Bike to Doe Bay

Highlights: Moran State Park and Doe Bay

If you’d like to get another ride in the morning we have a great route though Moran State Park to Doe Bay. After returning to Eastsound, enjoy exploring town before we gather again for our farewell group dinner.

Hotel: Outlook Inn

  • Distance: 35km (22mi)
  • Gain: 701m (2300ft)
  • Terrain: Hilly
  • Day Level: difficulty level 3.0
  • Meals: Breakfast
Travel Information

Travel Information

Pre-Trip Planning Checklist

To Do Today!

  • Read through your Reservation Confirmation Email, it has important information to help you plan your trip!
  • Check the date on your passport. The expiration date should extend three months past your date of return to your home country
  • Complete the Customer Information Form online at
  • Apply for trip cancellation/interruption insurance within 15 days of booking. Find details at this page
  • Download the bicycle training program found on the Training Program Blog Page at

3–6 Months Prior to Departure

  • Reserve your flights after you know you have a confirmed tour departure. Please check with our office if you do not know if your trip is confirmed. As you make your plans refer to the Getting To and Away sent to you in your booking confirmation email it provides meeting times and the starting and ending hotels and shuttle information when applicable.
  • Book your pre and post-tour hotel nights. Please refer to the Getting To and Away sheet you received in your Reservation Confirmation Email.
  • 12 weeks before your tour begin your training program found on this page.
  • Final payment is due 90 days prior to the tour start. Please refer to your Deposit Payment Invoice and the Final Payment Reminder e-mail you have received for detailed instructions.

6 Weeks–2 Weeks Prior to Departure

Day of Your Flight

Get as much sleep on the plane as you can. Pack your Getting To and Away information and one day of cycling gear in your carry-on. See you soon!

What to Expect on Tour

Classic Tour Style

Learn more about what is included and what to expect on your Classic tour at the Classic page.





Awards, Memberships and Reviews