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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 a night each on Lopez, 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 Lopez, where you’ll get a gentle start on the flattest terrain of the itinerary. The quietest of the islands, Lopez has bucolic farmland and friendly locals. Next, you’ll test your mettle on Orcas island with a challenging ride up the 2,400-foot Mt. Constitution. Your third and final island destination will reward you with an exciting and varied ride around San Juan Island. Top it all off with a celebratory final night in the lively town of Friday Harbor.

What To Expect

This bike tour is moderate, with average daily rides of 36 miles. It offers a day ride on all three islands: Lopez, Orcas, and San Juan Island. The route includes coastal and rural riding, with rolling terrain and one sustained ascent/descent on Mt. Constitution. Each day includes a ferry to the next island, with one night in each location. If you want to ride the best of the San Juan Islands, enjoy hand-picked inns, and reward yourself with savory local seafood at the end of your ride, then this action-packed tour is for you!

Trip Style:

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


Inn to Inn Cycling, E-Biking | A classic point to point cycling holiday, staying in a different location each night, E-Bikes with electronic motors to assist available to hire on this holiday (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

Grade & Terrain

This tour is moderate with daily distances varying from 18 – 36 miles, and an average of 26 miles. This route 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. The only 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 (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. 

Accommodation Information

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 a nearby restaurants see your info pack or ask your hosts for suggestions.

  • 4 Nights in B&Bs/inns
  • 4 Breakfasts
  • Bike rental
  • Washington State Ferry fares
  • Baggage transfers between inns and ferries
  • Detailed pre-departure information pack
  • Route notes with maps
  • Macs Adventure Navigation App
  • 24/7 US 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 flyin 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).

Baggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20 kg per person.


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.

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 Harbour 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 miles / 33 km Day 5 Ferry to Anacortes and Onward Travel 4.5 miles / 7 km

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