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San Juan Islands Biking Short Break

5 Days & 4 Nights 4.8 Read 4 reviews
  • Bike the highlights of Puget Sound’s Lopez, Orcas, and San Juan Islands
  • Island-hop via the Washington State Ferries
  • Watch for iconic Pacific Northwest wildlife: orcas, seals, otters & bald eagles
  • Taste local favorites, from hoppy craft beers to fresh oysters
  • Relax in boutique hand-picked inns on each island
Bike the highlights of the San Juan Islands over five days, spending evenings on Orcas and San Juan Island. Pedal the best of the region—a cyclist’s dream come true, complete with exciting bike rides, coastal views, and indulgent country inns. From the port town of Anacortes, catch your first ferry to Friday Harbor. The lively town serves as an exciting start to your adventure. Next, you’ll test your mettle on Orcas island with a challenging ride up the 2,400-foot Mt. Constitution. An optional ride on Orcas Island completes your experience.
This bike tour is moderate and includes day rides on San Juan and Orcas Islands, offering a glimpse into this areas landscapes and way of life. The routes offer coastal and rural riding, with rolling terrain and one sustained ascent/descent on Mt. Constitution. With 2 nights in each location you can relax and enjoy hand-picked inns whilst rewarding yourself with savory local seafood at the end of each exhilarating day.

Tour Style:

Self Guided | Go at your own pace on an independent tour.


Inn to Inn Biking, E-Biking | A classic point to point biking tour, staying in a different location each night, E-Bikes with electronic motors to assist available to hire on this tour (subject to availability), to make things easier

This trip is suitable for:

Multi-Generational, First Timers

Ideal if you have an interest in:

  • Wildlife
  • Coastal & Island


  • Most Popular

Activity Level & Terrain

This tour is rated moderate and the routes follows a combination of coastal and rural roads, as well as busier roads entering and exiting towns. You should be comfortable sharing the road with other users and be considerate of traffic regulations.

Most of the riding is on rolling terrain at sea level, however it is definitely not flat and there will be elevation gains and losses involved. The only significant sustained ascent is Mount Constitution, a ride from the coast to the summit at 2,400 feet (with alternate activities available). Each day’s ride is flexible due to the nature of the island-hopping itinerary and circular routes. For those looking for a little extra assistance, e-bikes are available at a supplement (subject to availability). The distances and ascents/descent listed are approximations of the recommended routes.


Navigating is easy using the Macs Adventure smartphone navigation app where you will find detailed maps, turn-by-turn route notes and GPX tracks for each daily route. All daily routes with GPX tracks are available to download for use offline. 


Carefully-selected, charming, and characterful inns will be your home on the San Juan Islands. All offer a warm welcome to cyclists and will help make your stay smooth as well as memorable.

Due to the lack of suitable accommodation on Orcas Island, you may be located elsewhere than Eastsound. Therefore please expect the the bike rides when not staying in Eastsound to be either longer or shorter than advertised. 

Single Rooms 

This trip is priced based on two people sharing a room. If you would like separate rooms, a single supplement is required. The San Juan Islands are a welcoming place for solo travellers but because of high solo supplement costs we don't offer the trip for solo travellers.


Breakfast is included each morning. All inns serve a filling, fresh, and plentiful breakfast; some include a hot dish while others provide coffee, juice, yogurt, granola, fruit, and baked goods. Please notify us of dietary restrictions at the time of booking.

Lunch and dinner are not included so you are free to choose from available nearby options. Depending on your timing it may be easier to pack a picnic lunch, while some days your route will offer dining options along the way. For dinner, be sure to sample some fresh seafood at nearby restaurants, ask your hosts for suggestions.

  • 4 Nights in B&Bs/inns
  • 4 Breakfasts (except when staying at the Inn at Ship Bay near Eastsound)
  • Bike rental (standard hybrid)
  • Washington State Ferry tickets from Anacortes to Friday Harbour and Orcas Island to Annacortes
  • Baggage transfers between inns and ferries
  • Digital trip and route information
  • GPS Navigation for your smartphone
  • 24/7 Telephone support
  • Travel to / from Anacortes
  • Optional upgrade to a road or e-bike
  • Lunches, dinners, drinks & snacks
  • Additional ferries between Friday Harbour and Orcas Island
  • Travel insurance (required)
  • Personal Equipment
  • Additional nights along the route
  • Upgrade to a road or e-bike

When To Go

Due to a change in nightly minimums in the area, this itinerary will not be available for the foreseeable future. As an alternative, we suggest our Classic or Short Break itineraries. 

Weather and Climate

Annually, the San Juan Islands boast 247 days of sun and about half the rainfall of Seattle due to the rain shadow created by the Olympic Mountains. Temperatures in the region are moderated by the Pacific Ocean and rarely rise above 70 degrees F or below 45 degrees F during our operating season, making it a perfect destination for an active adventure.

Getting to the Start

By Air:  We recommend flying into and out of Seattle Tacoma International Airport (SEA) from were you can easily take a shuttle directly to/from Anacortes (2.5 hours). You may also choose to rent a car at SEA and drop it off when you reach Anacortes (1 hour 45 minutes) and vice versa after your tour.

Alternatively, you can fly into and out of Vancouver International Airport (YVR), from where you may choose to rent a car. Alternatively, there is train service from YVR via the Canada Line and Expo Line (30 minutes) connecting to the Amtrak Cascades from Vancouver to Bellingham (2 hours). There is also Greyhound bus service between Vancouver and Bellingham (2 hours 15 minutes). However, if you choose to train or bus from/to Vancouver, you will need to arrange a private transfer between Bellingham and Anacortes (45 minutes).

Luggage Transfer

Your bags will be transferred per your itinerary between your accommodation and ferries. It is your responsibility to travel with your luggage while on the ferry. We ask you to limit your luggage to one bag of up to 20 kg per person and also make sure that your luggage has wheels and is easy to manoevre. 


Our pre-departure information pack has detailed advice on what to bring. Please be prepared by packing all necessary items, including rain gear, sunscreen, and appropriate cycling clothing, as the weather can vary greatly. If you have any questions, we would be happy to share our tips and advice.  Please limit your baggage to 1 bag per person of no more than 50 lbs / 20 kg. Your bag will be transported between your inns and the ferries.

Bike Rental

Hire of a Trek 7.3 FX hybrid bike, helmet, lock, rear rack, waterproof bag, flat repair kit, water bottle cage, and bell are included in the trip cost. If desired, Specialized Rubaix carbon roadbikes are available for an additional charge. If you would like them, please provide your own clipless pedals, shoes, and saddle. These can be installed and adjusted for you upon arrival. Please supply us with your height for your bicycle rental so we can make sure you bike is the perfect fit. E-bikes are also available should you want a little extra assistance to help you along the way. These are subject to availability and require a supplementary payment.

You will need to be prepared to take your bikes on the inter-island ferries. When travelling on the ferry between Friday Harbour and Orcas Island, both your own luggage and your bike will need to be wheeled onto the ferry. 

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page.

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Day 1 Arrive Anacortes, Ferry to Friday Harbor Day 2 San Juan Island Loop Ride 29 miles / 47 km Day 3 Ferry to Orcas Island, Ride to Eastsound via Deer Harbour 17 miles / 28 km Day 4 Ride Mt Constitution 20.5 miles / 33 km Day 5 Ferry to Anacortes and Onward Travel 4.5 miles / 7 km

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