San Juan Islands Women’s Cycling Weekend

Trip Length 4 Days
Group Size 4–12
Activity level
Starting from
$1,699 for REI Members
$1,849 for non-members
Departures Jun 2023-Aug 2023

Delight your senses on a 4-day women’s camping, cycling and culinary adventure through the gorgeous San Juan Islands.

The San Juan Islands offer a treasure trove of jaw-dropping scenery, world-class cycling, quaint oceanside campsites, and mouthwatering local food and wine. We’ll spend our four days on the islands experiencing a diverse array of culinary and cycling highlights while enjoying the company of new friends and fabulous women guides.

Spectacular San Juan Island, with a cultural history as rich as its biodiversity. Charming Lopez Island, with its rolling farmlands and friendly locals who greet you with a smile and a wave. And Orcas Island—"the gem of the San Juans"—home to Mt. Constitution and unparalleled opportunities for outdoor adventure.

Every day of our trip is an inspiring journey through the heart of each island, and every night is spent fireside, feasting on locally inspired meals and delicious regional wines.

Gathering around the campfire to recap the day’s adventures.

Trip Highlights

  • A beautiful ferry ride between the crown jewels of San Juan, Lopez, and Orcas Islands
  • Cycle along stunning ocean shoreline, through pastoral farmlands, and amidst verdant emerald green forests
  • Conquer Mount Constitution, the highest point in the San Juan Islands
  • Feast on locally inspired meals paired with delicious regional wines at each of our cozy campsites
  • Enjoy awesome views and the opportunity to spot local wildlife from historic lighthouses
  • Celebrate each day’s accomplishments with a group of likeminded women travelers


This trip is rated Moderate [3-4]. Participants should be experienced riders who are comfortable in the saddle for 4-6 hours per day; they should be comfortable riding paved, chip-seal roads with light vehicle traffic.

Rides range from 25–35 miles per day. Terrain is hilly with a few steeper ascents and descents. Elevation gains and losses range between 1,700'–3,800' each day. Most hill gradients average 3–6% and a few steeper points can reach up to 10% grades. E-bikes are available in a limited quantity upon request.

Participants should come equipped with a spirit of adventure and willingness to pitch-in and help with camp chores when necessary.

  • Road Cycling
  • Cycling

What's Included

Two professional guides; all meals as noted in the daily itinerary; transfers as noted on the daily itinerary; wine tastings at each dinner; tent; sleeping pad; group cooking and camping gear; all park fees and permits. Guest’s choice of a Drop Bar Road Bike, or a Drop Bar e-bike (based on availability).


Camping, 3 nights

Your wheels for the journey

Every great tour begins with a great bike, and our top-flight fleet has been carefully curated for your cycling adventure.

Want to bring your own bike?  You can do that too.

Your Adventure Itinerary

Itinerary map for San Juan Islands Women’s Cycling Weekend

Important Itinerary Note:

Please note that due to the elevated food and wine pairings experience on this itinerary, there is a slight price difference compared to our standard itinerary. If you would prefer an experience without elevated food and wine pairings, please see our San Juan Islands Weekend Cycling.

Day 1

Visit the historic lighthouses and world-class wildlife viewing perches of San Juan Island

Our trip begins this morning on beautiful San Juan Island at the Friday Harbor ferry terminal. After brief introductions, a short transfer and bike fitting, we hop on our bikes for a ride to Cattle Point Lighthouse, which sits on the south end of the island. Along the way, our guides share the inspiration behind its name and insights into the contentious history of San Juan Island. After lunch we’re off on our ride to Lime Kiln State Park, considered by some to be one of the best shoreline viewpoints in the world to spot whales. At the end of the day we make camp at one of the island’s favorite resorts where we enjoy a delicious meal and get to know our fellow cyclists better. Lunch and dinner included.

Cycling: 35–38, Elevation gain/loss: 2,398'

Day 2

Cycle the rolling hills, scenic shorelines and forested roads of charming Lopez Island

After a hearty breakfast we break camp, pack up, and set out for a morning stroll through Friday Harbor. We then hop aboard a Washington State ferry for a quick sail to Lopez Island. An idyllic location for decompressing, Lopez also offers miles of quiet, scenic country roads—perfect for a day in the saddle. Our expert guide team has weaved together an exceptional cycling itinerary that takes us through farmland, forest and shoreline. At the end of the day we round out our sensory experience with an indulgent and well-deserved dinner and wine pairing in camp. All meals included.

Cycling: 32 miles, Elevation gain/loss: 1,680'

Day 3

Get your heart pumping with a ride up and down Mount Constitution

Our first four miles of the day take us from camp to the ferry terminal, where we hop aboard for a short jaunt to Orcas Island. After disembarking, we head straight from the ferry terminal to the historic village of Eastsound where we enjoy a guide-prepared lunch. We’re then back on our bikes for a six-mile ride to Cascade Lake, a perfect warmup for our push up Mt. Constitution, the highest point in the San Juan Islands. While our five mile ride up the peak is a challenge, the 360 degree views from the top make our hard worth work it. On a clear day, views extend to Mount Baker, the North Cascades, British Columbia’s Gulf Islands, and the rest of the San Juan Islands archipelago. Tonight we enjoy a final dinner and wine celebration at our cozy state park camp site. All meals included.

Cycling: 27 miles, Elevation gain/loss: 3,826'

Day 4

Explore Eastsound and Deer Harbor before our ferry ride home

After breaking camp and loading up our sag wagon, we’re off on a ride back to Eastsound. We take time to explore the quaint corners and charming stores in the village before riding to Deer Harbor Preserve for lunch at a pretty oceanside perch. Should time allow, we'll ride the last few miles back to the ferry terminal where we bid our new friends and the San Juan Islands a fond farewell. From here, each group member is on their own to decide whether they’ll return to Anacortes or explore more of the islands on their own. Breakfast and lunch included.

Cycling: 25 miles, Elevation gain/loss: 1,681'.

Itinerary map for San Juan Islands Women’s Cycling Weekend

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.

Collection of selected R E I Co-op cycling merchandise and snacks laid out to pack for a bike tour

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.