San Juan Islands Cycling - Lodge Based

Trip Length6 Days
Group Size4-12
Activity level
Starting from
$3,649for REI Members
$4,004 for non-members
DeparturesJul 2025-Sep 2025

Ride along the whale-spotted beaches and quaint towns of Washington's iconic San Juan Islands for six glorious days.

Experience the joys of climbing Mount Constitution, the highest peak in the San Juan Islands. Capture stunning views from the summit and on the descent as the sun reflects off the myriad inlets. Stay in unique, classic accommodations and savor locally-sourced meals at local restaurants or enjoy culinary delights prepared by our guides. Our San Juan Island property features private hot tubs for a relaxing soak under the starry Pacific Northwest sky before you turn in for the evening.

An early sunset looking west out over Haro Strait from the Lime Kiln Lighthouse.

Trip Highlights

  • Get a taste of island life of the Pacific Northwest while cycling the San Juan Islands
  • Explore scenic villages with local shops, marinas, and restaurants
  • Cycle among snowcapped peaks, bountiful islands, and beautiful beaches
  • Climb to the summit of Mount Constitution, followed by an exhilarating descent

Activities

This trip is rated Moderate [3]. Participants should be experienced riders who are comfortable in the saddle for 2-6 hours per day; they should be comfortable riding paved chip-seal roads with light vehicle traffic.

Rides range from 15-35 miles per day with the ability to add a few more miles on some days. Terrain is hilly with a few steeper ascents and descents. Average elevation gains and losses are 1700' per day, not including the optional ride up Mt Constitution which is 2,200'. Most hill gradients average 3-6% and a few steeper points can reach up to 10% grades or higher. Vehicle support is always available when needed.

  • Cycling
  • Road Cycling

What's Included

Five nights accommodations; all meals as noted in the daily itinerary; wildlife watch cruise, ferry ride tickets between islands; two professional guides; transfers as noted on the daily itinerary; all park fees and permits. Guest's choice of a Drop Bar Road Bike, or a Drop Bar e-bike (based on availability).

Accommodations

Inn and Luxury yurt accommodations; 5 nights

Your Adventure Itinerary

Itinerary map for San Juan Islands Cycling - Lodge Based
Day 1

San Juan - Ferry to Friday Harbor, begin our cycling adventure!

We will greet everyone this morning at Memorial Circle in Friday Harbor, WA, a short walk from the Washington State Ferry terminal. Luggage and guests will be loaded into the van and trailer for a short transport to Jackson's Beach for our orientation. While enjoying our first lunch together, our guides will brief the group on local island knowledge, safety and bike fit. The start of our ride will meander through open pastures and prairie land before encountering the first of the rolling hills we will experience over the next few days.  Continuing along todays route, we crest a hill only to be greeted with the first epic view of the Straight of Juan De Fuca and Olympic Peninsula. The day continues with a visit to Lime Kiln State Park, the Alpaca farm, English Camp National Historical Park, and into the village of Roche Harbor. Enjoy a stroll around the sculpture park, the formal gardens, or a coffee and donut from the café. We finish the ride at our accommodations for the next 3 nights; the lavish Yurts at Lakedale Resort; complete with spacious accommodations and hot tubs at each yurt. Lunch and dinner included.

Cycling: 26.8 miles; elevation gain/loss: +2035’/-1654'.

Day 2

San Juan - Meander a prairie ecosystem along the Salish sea to a lighthouse

Our guides will prepare a hearty breakfast before we start our day riding south through the open meadows of Beaverton and San Juan Valleys towards False Bay. With our first views of snow-covered Mount Baker we make our way further south into the prairie ecosystem rarely found in western Washington. Riding through American Camp we ride the peninsula with expansive views of the Salish sea and the Cascade and Olympic mountain ranges on each side. We will eat lunch at the southernmost point of San Juan Island known as Cattle Point Lighthouse. Returning home to clean-up, we will soon head back to Friday Harbor for a meal at one of the local's favorite restaurant. All meals included.

Cycling: 30.6 miles; elevation gain/loss: +1775'/-1777’.

Day 3

San Juan - Spot local island treasures from shops to whales and wildlife

We start the day with an early breakfast before embarking on a scenic 5-mile pedal to Friday Harbor. From here, we board our boat and enjoy a morning marine wildlife cruise, followed by a delightful lunch near Friday Harbor with time to explore the shops. Giving our cycling muscles a rest, we’ll hike to the top of Young Hill, where you'll be rewarded with breathtaking views of the islands. Our day concludes with a delicious dinner at a local restaurant. This low-mileage day is packed with exploration and discovery of island treasures. All meals included.

Cycling: 5 miles; elevation gain/loss: +211’/-413': Hiking 2.2 miles; elevation gain/loss 587'.

Day 4

Lopez/Orcas - Explore Lopez island's expansive beaches then ferry to Orcas

Up early this morning, we have a ferry to catch. After a guide prepared breakfast, we shuttle to Friday Harbor to catch the early morning ferry to our day on Lopez Island. From the ferry terminal we will ride down the west coast of the island to Lopez Village where we can explore the shops before a guide prepared lunch at Shark Reef. The afternoon brings a visit to Agate Beach Country Park for eastward views of the North Cascades. The interisland ferry leaving mid-afternoon will bring us to Orcas Island. We transfer from the ferry terminal to our lodging in Eastsound for the next 2 nights. All meals included.

Day 5

Orcas - Summit San Juan's highest peak then descend to a crystalline lake

After a filling breakfast we load up in the van for a quick shuttle to Cascade Lake in Moran State Park. After a brief warmup, we start our climb up Mt. Constitution, 5.2 miles, 2000 feet of elevation gain. We will have a picnic lunch at the top of the Mount Constitution summit with views of Bellingham, Mount Baker, and Rosario Strait. An exhilarating downhill back to Cascade Lake and a gentle downhill ride to Eastsound awaits us. We have time to explore the shops in Eastsound or a stroll along the beach before dinner. All meals included.

Cycling: 15.8 miles; elevation gain/loss: +2269'/-2620’.

Day 6

Orcas - Cycle through enchanted forests and lunch al fresco then bid farewell

We begin our final ride of our time together after breakfast. Heading back west, we leave Eastsound via the aptly named Enchanted Forest Road. As we meander through the forest, we ride past open pastures to our lunch stop along the way. We will ride to picturesque Deer Harbor before turning back for our final miles to the Orcas ferry terminal. We bid farewell as guests board a late afternoon ferry to Friday Harbor or back to Anacortes. Breakfast and lunch included.

Cycling: 19.5 miles; elevation gain/loss: +1534'/-1506’.

Itinerary map for San Juan Islands Cycling - Lodge Based

Gear List

The key to staying comfortable while on an active trip is layering. To get maximum comfort with minimum weight, you need versatile layers that mix and match to create the right amount of insulation, ventilation and weather protection. Try to bring only what is necessary—this will help you and the field staff.

Already booked this trip? Sign into your online traveler profile for a more detailed list of what you'll need.

REI members can shop for gently used gear online or at most REI stores. Members can also trade in pre-loved used gear online or at any REI store in exchange for REI gift card credit. Check out Re/Supply at REI to learn more.

We provide

What to pack

Contact Us

Feel free to give us a call at 1 (800) 622-2236 should you have any questions regarding the gear list. The staff at our stores and Direct Sales ( 1 (800) 426-4840 ) will also be happy to help you with gear questions. Or check out REI Expert Advice , which has great information to help you prepare for your trip.

Trip specifics may change over time. Reviews reflect the version of the trip that was active at the time the reviewer took it. Please review the itinerary as described above and call our team for any additional details.