Self Guided Walking Holidays & Cycling Holidays

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San Juan Islands Biking Classic Self-Guided Biking Tour


  • Bike the best of Puget Sound’s San Juan Islands
  • Travel the Salish Sea by ferry as you hop from island to island
  • Watch for wildlife: orcas, seals, otters, and bald eagles
  • Relax at boutique inns each night after your day’s ride
  • Savor locally-caught seafood, from Buck Bay oysters to Pacific salmon

Cycle the best of the San Juan Islands, hopping from island to island by ferry. Ride Lopez, Orcas, and San Juan Island, never straying far from the waters of Puget Sound.

Soak in the laidback island vibes as you make your way from sparkling coves through verdant old-growth forests and past rolling farm fields. At a relaxed pace, you’ll have plenty of time to tide pool, walk a stretch of rocky beach, observe the bountiful marine wildlife, or stop at a local art gallery.

You’ll spend two nights on each of the three largest islands in the San Juans - each with a different personality and unique sights, flavours, and destinations to offer. After a full day of exploration, treat yourself with a meal of local seafood and a warm welcome from the host at your boutique accommodations.

Day 1: Arrive Anacortes

Easily accessed from Seattle, Anacortes makes a great jumping-off point for the islands. We recommend taking a shuttle directly from Seattle-Tacoma International Airport (2.5 hours). Spend the evening exploring the seaport of Anacortes, perhaps with a walk to the marina or your first taste of fresh-caught Pacific seafood. 

Overnight: Anacortes

Day 2: Ferry, Ride to Lopez Village & Fisherman Bay Preserve

After a quick orientation to your rental bike, a short ride will take you to the Anacortes ferry terminal. Kick back and enjoy your first ferry (approx. 45 minutes) as you travel from Fidalgo Island to Lopez Island. Once you reach Lopez, also known as “The Friendly Isle”, it’s a short ride to your boutique inn.  There is plenty to explore this afternoon with a recommended ride to Fisherman Bay Preserve.

Cycle: 10-18 mi. (+/- 600 ft.)

Overnight: Lopez Village

Day 3: Lopez Island Loop Ride

With a reputation for its laidback atmosphere and relatively flat topography, Lopez Island is truly a bicyclist’s paradise. Pedal past farm fields and along rocky coves, taking time out of the saddle to walk to Iceberg Point, part of the San Juan Islands National Monument. At ride’s end sit back with a unique island-grown wine and enjoy the seaside view of the setting sun. 

Cycle: 25 mi. (+/- 1450 ft.)

Overnight: Lopez Village

Day 4: Ferry to Orcas Island, Ride to Eastsound

Aboard the ferry (approx. 35 minutes), keep an eye out for the wildlife of Puget Sound: orcas often steal the show but you may also catch a glimpse of sea lions, harbor seals, and bald eagles. Upon landing on Orcas Island, also known as “The Emerald Isle” for its verdant hills, you’ll have a chance to stretch your legs with a ride on its western half. Stop for lunch in the hamlet of Deer Harbor to fuel up for the rolling terrain on your way to Eastsound, the largest village on the island.

Cycle: 23 mi. (+/- 1420 ft.)

Overnight: Eastsound

Day 5: Day Ride Mt. Constitution

With your legs accustomed to riding, you’ll be ready to tackle Mt. Constitution, the highest point in the San Juan Islands at 2,400 ft. Heading to Moran State Park, the coastal road will soon turn inland and you’ll find your route flanked by old-growth fir, spruce, and cedar giants. After a challenging but rewarding ascent, Mt. Constitution boasts views of the North Cascades Range, including glacier-capped Mt. Baker, on a clear day. Explore the stone tower atop the summit; built in the 1930s by the Civilian Conservation Corps, it is a replica of the 12th century Russian Caucasus watchtowers.

As an alternative to this heart-thumping ride, enjoy a walk along one of Moran State Park’s many winding trails, opt for a free day in Eastsound to visit the eclectic art galleries and museum, or go on a wildlife and whale watching tour (separate booking required).

Cycle: 25 mi (+/- 3550 ft.)

Overnight: Eastsound

Day 6: Ride to Ferry, Ferry to San Juan Island, Ride to Cattle Point

After a quick ride back across Orcas Island, you’ll hop aboard your next ferry (approx. 45 minutes). A perfect final destination, the bustling town of Friday Harbor greets you as you step onto the biggest of the San Juan Islands. With its shops, restaurants, galleries, and marina, you may be reluctant to pedal away, but rest assured you’ll be back this evening. Head south to Cattle Point, swinging by driftwood-strewn South Beach on your return for a view of the snowy peaks of the Olympic Range across the waters of the Salish Sea. 

Cycle: 36 mi. (+/- 2316 ft.)

Overnight: Friday Harbor

Day 7: San Juan Island Loop Ride

Enjoy a leisurely loop ride around the island, leaving time to make plenty of stops. At Lime Kiln Point State Park, snap a photo of the iconic lighthouse and watch for marine wildlife cruising up the coastline, including resident orca pods. At Roche Harbor, take a break from pedaling for a walk among forests, gardens, or boat slips. Perhaps you’d prefer to stop by a lavender farm, an alpaca ranch, or a vineyard for a wine-tasting. With a full day to explore its many delights, San Juan Island offers something for everyone. 

Cycle: 29 mi. (+/- 1320 ft.)

Overnight: Friday Harbor

Day 8: Ferry to Anacortes & Onward Travel

Relax for one last morning on ‘island time’, and then ferry back to Anacortes (approx. 1 hour 5 minutes). From there, you may opt to take a direct shuttle to the airport or continue your adventures in the Pacific Northwest. 

Cycle: 5 mi. (+/- 400ft.)


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 small, family-run nature of the lodging we choose, we may at times have to accommodate you at an alternative location due to availability. Any alternative will be similar in style and level of comfort to the properties listed here.

Solo Cyclists & Single Rooms

This trip is priced based on two people sharing a room. If you’d like separate rooms, a single supplement is required. This trip is also available to solo cyclists and a supplement is required.  The San Juan Islands’ welcoming and slow-paced atmosphere makes this a great place for solo cycling.


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 restaurant—see your info pack or your hosts for suggestions.

Extra Nights

You can easily add extras nights during this itinerary. For further details, please ask us at the time of booking. 


Nantucket Inn

Nantucket Inn

An updated and elegant colonial home, the Nantucket Inn is run by Jessica and Mike, Skagit Valley experts. The property has unbeatable views and location, within walking distance to town, and your stay includes signature hot breakfasts.




Edenwild Inn

Edenwild Inn

Located in Lopez Village, the Edenwild is run by Anthony, Crystal, and their family. Feel easily at home in their gorgeous, award-winning B&B and fuel up on hearty homemade fare in the morning.




Outlook Inn

Outlook Inn

This historic landmark property in the center of Eastsound offers hospitality down to every last detail, including outstanding views, service, and dining. With an emphasis on ‘deep rest’, innkeeper Sara and her team strive to provide a restorative experience, including the fresh-focused French restaurant on site.





Tucker House Inn

Unique, indulgent, and well- located in Friday Harbor, this inn offers historic rooms, peaceful gardens, and gourmet meals. Friendly hosts Anna and Dave will answer any questions you have about the island.


This tour is available from May to October. You can start on any date subject to availability. The San Juan Islands are a popular vacation destination with limited lodging capacity, so it is best to book as far in advance as you are able.

When To Go?

The best months to visit the San Juan Islands are May to October. May, June, September and October will typically be less busy than July and August. Whale sightings are most common between May and September. 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.


Navigating is easy using the Macs Adventure Navigation App. All daily routes with GPX tracks are available to download for use offline. Along with this app, you will also receive turn-by-turn directions and maps in your pre-departure information pack.

You will be provided with local bike shop information in addition to 24/7 telephone support from Macs Adventure should you require assistance. However, cell phone service is not always reliable in parts of the San Juan islands.

Experience, Fitness & Grade

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 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 may be an option but are subject to availability. The distances and ascents/descent listed are approximations of the recommended routes.


Our pre-departure information pack has detailed advice on what to bring. Please be prepared by packing all necessary items, including but not limited to, proper 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. Your bag will be transported between your inns and the ferries.

Bike Rental

A bike renal is included in the cost of this trip. This includes a Trek 7.3 FX hybrid bike, a helmet, lock, rear rack, waterproof bag, flat repair kit, water bottle cage, and bell. If desired, Specialized Rubaix carbon road bikes 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 rental.

There are a limited number of e-bikes available should you want a little extra assistance. These are subject to availability and require a supplementary payment.

Please supply us with your height for your bicycle rental.

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 by clicking this link.

Getting to & from Anacortes

If you fly into (or out of) Seattle Tacoma International Airport (SEA) (strongly advised), you can easily take a shuttle directly to/from Anacortes (2.5 hours, 11 departures daily). You may also choose to rent a car at SEA and drop it off when you reach Anacortes (1 hour 45 minutes drive) and vice versa after your tour.

If you fly into (or out of) Vancouver International Airport (YVR), you may also choose to rent a car. Alternatively, there is train service from YVR via the Canada Line and Expo Line (30 minutes total) which connects 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 get a private transfer between Bellingham and Anacortes (45 minutes).


  • 7 Nights in B&Bs/inns
  • 7 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
  • Lunches, dinners, snacks, and drinks
  • Travel insurance


  • Additional nights before, during, or after your trip
  • Single room or solo cyclist supplement (if required)
  • Road bike or e-bike upgrades

What happens if I can’t cycle a stage?

The great thing about this itinerary is that the ferry will bring you to the next island each day. You can typically get from the ferry terminal to the next inn by riding only a few miles and not a whole day. The longer suggested routes are circular, rather than point-to-point so if you are not up for biking the entire route, you can turn around at any point. In some places, there are also taxis; specifics on local taxis can be found in your pre-departure information packet.

What do I do if I become ill during my trip?

This trip allows for plenty of flexibility, so if you’re not up for riding that is okay. If you need medical services, you’ll find information in your pre-departure information packet or you can ask for assistance at your inn. As always, 24/7 support from Macs Adventure is only a phone call away.

How do I get my rental bike?

Your rental bike will be arranged through a local bike shop at the starting point of your trip. We will set this up ahead of time and provide all necessary details in your pre-departure information packet. You will pick up and drop off your bike at the rental shop so that our local partners can help adjust the bike to you.

San Juan Cycling


This was a great trip. Macs adventure made our experience relatively seamless. The transitions of moving from island to island was peacefully orchestrated. The accommodation were lovely and inviting. We love the independence of the self guided cycling. We have one big suggestion though. The mapping for the rides ( to open the app and read directions at each corner ) was not seamless. I suggest they offer "Ride with GPS" so that we could listen to directions and not have to stop so often. To enjoy the scenery along the way.


Reno, nv


Beautiful scenery, quaint inns, no shoulders


We really enjoyed our trip to the San Juan Islands. The coast was beautiful. The orcas didn't show themselves though. The biking was more taxing than we expected (we're from Michigan), so we just took public transit on our last 2 days. Loved that feature of being able to change plans on the fly without a group to reckon with. Shan did a great job of answering my questions. The accommodations were perfect. Mac's still needs to iron out a few wrinkles with the service providers, but almost there! (i.e. one breakfast was not served as the restaurant was closed, luggage transporters unsure of our schedule, bike shop did not show up early to give us our bikes). But overall a great experience that we recommend!

Josh the Midwesterner

Holland, MI


San Juan Islands Biking Classic

4.5 2


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