San Juan Islands Kayaking and Camping

San Juan Islands, Washington
Pack Sea Kayaking, Hiking, Camping, Whale Watching
14 Explorer Chicks
5 Days


Read HERE for info on 2023 Dates.


Discover the abundant wildlife and lush landscapes! Get ready for sea kayaking and camping in the San Juan Islands in Washington for women only. As soon as your feet land on San Juan Island, breathe in the clean air. Next, set your watch back to island time. Over the next 5 days, you’ll explore Orcas Island, San Juan Island, and Stuart Island by foot and paddle while enjoying a combination of glamping and traditional camping in the backcountry.

Orca Whale Watching and Other Wildlife Spotting

The San Juan Islands are famous for their Orca whales. You bet we’ll set sail to catch a glimpse! You’ll kick off your San Juan Island adventure with a guided whale watching tour at sunset. The archipelago is also home to a wide range of wildlife including bald eagles, harbor seals, river otters, Steller sea lions, common minke whales, and Dall’s porpoise. In the evening, you can head out to the shoreline for some tide pooling.

San Juan Island Gamping

After meeting your newest adventurous gal pals in Friday Harbor on Day 1, you’ll settle into your glamping digs—a home sweet home for your first two nights. You will be living like a Wilderness Queen! These canvas tents are equipped with all the comforts of home and decks that screams, “Pull up a seat and a cold one.”

Guided Hiking and Winery Visit on Orcas Island

Orcas Island is the largest of the San Juans, boasting dense greet forests, mountain lakes and endless adventures. After hopping a ferry in the morning, you’ll spend an entire day exploring the island’s best trails including a steep hike to the highest point: Mount Constitution. But the climb will be worth it! Cast your eyes upon the rugged coastlines, expansive ocean views, and snow covered mountains. We’ll even squeeze in time for a picnic lunch and a winery experience.

Multi-day Guided Sea Kayaking Adventure and Backcountry Camping

The San Juan Islands offers up some of the best sea kayaking in the world. You’ll spend the last three days backcountry kayaking to, and then exploring, Stuart Island. We’ll load up our two-person kayaks “expedition” style. This means carrying all of our camping gear, food, and personal items required for the next three days. Can you say girl power? Paddling up to 15 miles, we’ll make our way across channels and straits to reach Stuart Island. Here is where we’ll set up our homey primitive camp for the next two nights. Your days will be spent hiking on the island, circumnavigating Stuart, or paddling to other nearby islands.

Gourmet Backcountry Meals Inspired by Local Chefs

Throughout your entire San Juan Islands trip, you’ll be spoiled with meals inspired by local chefs. Your guides will be cooking up some of the best backcountry meals you’ll ever sink your teeth into—with organic, fresh, and locally sourced ingredients. Cheesecake in the backcountry? YOU deserve it, sister! Oh, and what’s a fancy meal without a wine pairing? Every evening you can take in the sunset with a regional wine or beer in hand. Yes, this is how you #adventurethencocktails.

Day 1 – Welcome to San Juan Island + Sunset Whale Cruise

You’ll kick off your San Juan Islands kayaking and camping trip at Memorial Park/Circle in Friday Harbor on San Juan Island at 12 PM. Your Explorer Chick Guide will be easy to find in her Explorer Chick apparel! Once everyone has gathered, we’ll transfer to our glamping home for the next two nights for an orientation and to quickly settle in.

We’ll squeeze in a short activity – like sea kayaking or hiking – to get to know each other better. Then we’ll board the boat for our Sunset Whale Watching tour. Our captain will not only keep his eyes peeled for the infamous orcas, but also for the other wildlife that calls these islands home.

Accommodations: Glamping

Meals: Lunch, Welcome Dinner, Snacks

Day 2 – Hiking Orcas Island and Winery Visit

After a hearty breakfast, we’ll take the ferry to Orcas Island. It’s the largest island in the San Juan Archipelago with lush forests, pristine mountain lakes, and views for days.

Lace up those hikers nice and tight, because we’ll be seeking out the best trails in Moran State Park. You’ll enjoy leisurely strolls around Cascade Lake and Mountain Lake keeping an eye out for bald eagles swooping down for a fresh catch. We’ll also take on the highest point of the San Juans: Mount Constitution. Climb the tower atop the 2,409’ mountain for views panoramic views of Mt. Baker, Mt. Ranier, and the rest of the snow covered Olympic and Cascade mountain ranges.

Naturally, (’cause we’re Explorer Chicks) all this hiking will be rewarded with a yummy picnic lunch plus a winery experience before taking the ferry back home to our glamping site.

Transfer: 20 minute ferry ride

Mount Constitution Hike: 6.7 miles/1,490’ gain

Accommodations: Glamping

Meals: B, L, D plus snacks

 Day 3 – Sea Kayaking to Stuart Island

It’s your first big day on the open water. Fist pumps all around! You’ll be paired up into kayaking teams and loaded down with a share of the camping gear, food, and your personal items in your expedition style sea kayaks. Your guides will review kayaking techniques and navigation before you set out for Stuart Island.

We embark from Roche Harbor on San Juan Island and cross the Speiden Channel with views of Speiden Island. The island was once used for big game hunting in the 1970’s-80’s. Although the hunting has been shut down, some of the imported animals continue to roam.

We’ll make a stop at yet another island to enjoy a picnic lunch on a pebble beach. Come late afternoon, we’ll drag our kayaks onto the shores of Stuart Island where we’ll make camp followed by some free time to relax. After dinner we can take in a sunset hike, an evening paddle, or just kick by the campfire.

Paddling: Approximately 5 hours and 7-10 miles

Accommodations: Backcountry Camping

Meals: B, L, D plus snacks

Day 4 – Day-tripping on foot and by boat

With our basecamp established on Stuart Island, you’ll enjoy an entire day of scoping out the trails and tiny coves along the shores. Today is flexible with the opportunity to go wherever our adventurous souls lead us. We could find ourselves hiking to Turn Point Lighthouse or paddling to more tiny islands like John Island and the Cactus Islands.

Along the way, be on the look out for the wildlife that call these islands home as your guide drops knowledge about the animal inhabitants and local history.

Once back at camp, your guides will prepare on last backcountry gourmet meal with the perfect wine pairings. Soak it all in, sista: the wilderness, the quiet, the disconnect, the gentle tide.

Paddling and Hiking: Varies, but a full day mix of both!

Accommodations: Backcountry Camping

Meals: B, L, D plus snacks

Day 5 – Return to San Juan Island and Departure

In the morning we’ll pack up our little backcountry home and load up our kayaks to paddle back to Roche Harbor. By this time, you’re a pro at sea kayaking and paddling is second nature. We’ll make our way back across the Spieden Channel still keeping our eyes peeled for seals basking in the sun on rocks.

Once back to Roche Harbor, you’ll have the chance to grab a quick shower at the marina before we transfer back to Friday Harbor. Here we must hug it out and say our, “See you later!”‘s. Plan to depart the island around 4:30pm.

Paddling: Approximately 5 hours and 7-10 miles

Meals: B, L plus snacks

*This itinerary is flexible, dynamic, and subject to change to provide you with the best experience. Routes are dependent on many factors including tides, weather, camp availability, group strengths, special interests, and group goals.

*Explorer Chick reserves the option to modify trip itineraries at the discretion of your adventure leader as necessary due to weather, conditions, illness, injury, group dynamics, safety, or other unforeseen incidents. If an activity must be cancelled due to conditions and cannot be rescheduled, your Explorer Chick guide will work to find alternatives or modifications to ensure the best value for your trip.

*If you choose not to do a specific activity we have planned, it cannot be exchanged or refunded.

  • 2 days/2 nights camping on San Juan Island with shared glamping tents – 2 per tent.
    • Big, beautiful Pinterest-worthy canvas glamping tents decked out with furniture and porches
    • Equipped with bedding, bath linens, tables and chairs, outdoor chairs, and fire pits
    • Shared shower house and restrooms
    • No electricity and spotty cell service
  • 3 days/2 nights backcountry camping with shared tents – 2 per tent
    • Includes shared tents, sleeping bag, sleeping pad, and pillow
    • Primitive camping with pit or compost toilet. No showers available.
  • Guided sunset Whale Watching tour including dinner
  • Gourmet Backcountry Meals as indicated in itinerary: B-4, L-5, D-4
  • 2 Happy Hour cocktails each evening from regional purveyors
  • 3 days of guided sea kayaking including instruction and safety gear
  • 1 full day of hiking on Orcas Island plus a winery experience
  • All state, county, and federal camping and hiking permits
  • All tips for included meals and local guides
  • An local guide through out the itinerary trained in kayak and open water safety.
  • An experienced Explorer Chick Guides ensuring your trip is seamless and unforgettable!
  • A commemorative Explorer Chick shirt and swag
  • A detailed Travel Guide upon booking with everything you need to know for your trip
  • The freedom to enjoy your vacation and mindlessly wander!
  • Small Group experience! Your Explorer Chick Adventure is exclusive and limited to 14 women

*Packages do NOT include your transportation to/from Friday Harbor on San Juan Island, additional alcoholic beverages, costs for additional activities, Travel Insurance, and Explorer Chick Guide tips.

*Does NOT include your Explorer Chick Guide’s Tips – Tipping your Explorer Chick Guide is optional, but customary. If you wish to recognize your Explorer Chick Guide for exceptional service, we recommend you tip 10-25% of your trip’s cost.

You will receive a travel guide attached to your booking confirmation with the rendezvous point, travel recommendations, and all of the information you’ll need to prepare for your trip. Plus, extensive details on how to get to Friday Harbor on San Juan Island.

Your trip begins and ends in Friday Harbor on San Juan Island. You are responsible for all transportation to and from our rendezvous point.

Arrival – Day 1: Arrive at Friday Harbor to our rendezvous point at 12pm.

Departure – Day 5: You are free to schedule your departure from Friday Harbor any time after 4:30pm.

How to get to Friday Harbor from Seattle

2 Options:

  1. Fly – Seattle to Friday Harbor
  2. Ground –
    1. Bus or Drive – Seattle to Anacortes
    2. Then Ferry – Anacortes to Friday Harbor

Rendezvous point is in walking distance of both the Ferry Terminal and the Island airport.

Full travel details including transportation service recommendations will be in your travel guide.

We recommend arriving a day early into Seattle, Anacortes, or Friday Harbor to avoid any problems with tight transportation schedules, delayed flights, tight or luggage.

Luggage and Packing: You’ll be provided a 20L and 5L dry bag for your personal belongings during the kayaking portion of the trip. Any unnecessary luggage will be locked up safely in storage.

You will spend the final 3 days of your trip, kayaking up to 15 miles and 6 hours per day with tides, waves, and currents. You will be paired with another Explorer Chick in an “expedition” style kayak that will be weighed down with gear. This trip can be enjoyed by beginners, but you should be in good physical condition. You can also expect some soreness/fatigue during the kayaking portion.

Kayaking stops and rests

Our daily kayaking routes will include stops to use “natural toilets,” rest, hydrate, and snack. However, when we have channel crossings there will be no chance to get out of your kayak. We’ll still be able to rest and hydrate, but you won’t be able to use the “toilet.” Channel crossings can take up to 2-2.5 hours.


Although you are not required to be able to swim, it is recommended so you’ll feel more comfortable in the open water.

We’ll also spend an entire day hiking on Orca Island. Hikes can include easier trails around Cascade Lake and Mountain Lake plus Mount Constitution. Mount Constitution is the highest point of the San Juan Islands with gorgeous views, but that view is earned!

Mount Constitution Hike

6.7 miles/1,490’ gain

Train your tootsies! Do not show up with brand new hiking boots, trail shoes, or water shoes. You should be spending hours upon hours in your shoes leading up to your adventure to break them in. Better to suffer blisters at home than to miss out due to painful hot spots on your feet. This is our number one injury. Do not let it happen to you!

Please consider your ability to meet the physical demands very seriously. It is for the safety of both you and our group. All Explorer Chicks will be required to sign an Acknowledgement of Physical Demands as part of their waiver upon booking.

Still not convinced that THIS is the adventure for you?

We’ve rounded up some of our most popular blog posts, so you can get to know us a bit better and learn what really goes down on your Explorer Chick Adventure.

You can always reach us by email with more questions!

To protect your travel investment and your hide, we highly recommend purchasing travel insurance. World Nomads is our trusted travel insurance provider. Receive an no-hassle, online quote in less than 2 minutes.

Questions? We love them! Check out our FAQ’s page first. You’ll probably find your answer there.

You can also send us an email.

Trip Price:

2022: $2,499

Save $200 with Early Bird Pricing!

See our Discount page for Codes and Expirations!

Non-Refundable Deposit: $200 due at booking to secure your spot

Payment Plans Available: Email after booking to set up your monthly payment plan.

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