San Juan Islands Kayaking – Roche Harbor to Stuart Island

Trip Length3 Days
Group Size4-12
Activity level
Starting from
$1,199 for REI Members
$1,299 for non-members
DeparturesMay 2024-Sep 2024

Explore the majestic San Juan Islands from the seat of a kayak on this unforgettable 3-day adventure.

Washington’s San Juan Islands are nothing short of magical. Its stunning landscapes and abundant wildlife make it a remarkable place to seek serenity and adventure. Our route is designed to take us through the best kayaking the San Juan’s has to offer. Paddling 7-10 miles per day, we pass tranquil beaches, observe marine birds and harbor seals, and spot the occasional orca from our boats.

From the quaint island community of Roche Harbor, we pack our boats and set out for a weekend of adventure. Spend two nights on charming Stuart Island, home to great hiking and beautiful campsites. While gliding through Haro Strait and Boundary Pass, we keep our eyes peeled for Dall's porpoise, endangered Steller sea lions and many different types of birds soaring overhead. Our guides are experienced naturalists, trained to help spot the creatures of the San Juan Islands. This journey hooks us with adventure and inspires us with beauty.

Interested in exploring more of the San Juans by kayak? Check out our San Juan Islands Kayaking – Orcas Island to Sucia Island adventure.

Another day draws to a colorful end in the San Juans.

Trip Highlights

  • Soak in the magic of Washington's San Juan Islands on an active weekend getaway
  • Spend two nights camping on Stuart Island while dining on local, organic food
  • Kayak 7-10 miles per day, explore the island by foot, and spot marine wildlife


This trip is rated Moderate [3]. We sea kayak up to 10 miles (up to 5 hours), in open ocean waters and crossing large channels that are frequently impacted by tides, currents, wind, choppy water, and possibly inclement weather. The crossing of large stretches of open water channels requires constant momentum sometimes without taking a break for large periods of time. Guests should arrive confident, comfortable, and fit for these conditions. Previous kayaking experience and the ability to swim is a requirement. For safety reasons, single kayaks are not available and guests will need to actively navigate an approximately 20' kayak in partnership with another person. While our guides will provide insight, planning, knowledge, and outdoor leadership during your trip, it is your responsibility to arrive physically and mentally prepared for your expedition.

  • Sea Kayaking

What's Included

Professional instruction and guiding; meals as noted in the daily itinerary; one group arrival transfer Friday Harbor-Roche Harbor; one group departure transfer Roche Harbor-Friday Harbor; 3-person tents for double occupancy use for 2 nights' camping; cooking gear and eating utensils; tandem kayaks (no singles); related kayaking equipment including paddles, PFDs and dry bags.


Island camping, 2 nights

Your Adventure Itinerary

Itinerary map for San Juan Islands Kayaking – Roche Harbor to Stuart Island
Day 1

Welcome to San Juan Island, paddle to Stuart Island to hike and camp

Our trip begins this morning in Friday Harbor, Washington, located in the San Juan Islands archipelago. We meet a few hundred feet from the Friday Harbor Ferry Terminal, then transfer to Roche Harbor to prepare for our kayaking excursion. Packing into dry bags, we load our kayaks and begin paddling across the open water of Spieden Channel and skirt Haro Strait, a favorite area for orca whale pods to find salmon. Tides and currents permitting, our picnic lunch stop will be on a picturesque beach on Posey, Gossip or Stuart Island. Returning to our kayaks, we paddle to Prevost Harbor on Stuart Island and set up camp for the next two nights. There is free time to relax, or perhaps head out for an evening paddle or hike. Tonight's dinner, made with locally sourced ingredients, is prepared by our guides. Lunch and dinner included.

Sea kayaking: 7-10 miles on open water with waves, tides, currents.

Day 2

Enjoy a full day of paddling around Stuart or Johns Island

After a delicious hot breakfast prepared by our guides, we load up our kayaks with lunch, water and snacks, then kayak around Stuart, Johns, and Spieden Islands. There are several wildlife refuges in the area, and it is not uncommon to observe marine birds and harbor seals in the hundreds. Porpoise are also a common sight throughout the day, and in Boundary Pass or Haro Strait we hope to see orca whales. We make several stops to eat lunch, take a short hike and enjoy the beaches. In the late afternoon we return to our camp and head out for a hike, or take time to relax and soak in the views. Dinner is prepared in camp. All meals included.

Sea kayaking: 8-10 miles on open water with waves, tides, currents. Optional hike: 2-4 miles

Day 3

Kayak through Boundary Pass and Haro Strait, return to Friday Harbor

Our final day on the water is spent paddling from Prevost Harbor towards Turn Point in Boundary Pass. We expect wonderful views of Mount Baker and the Canadian Cascade Mountains. Reaching Haro Strait, a clear day brings views over 100 miles to the south of the Olympic Mountains. After a break for lunch on the west side of Stuart or Posey Island, we paddle to Roche Harbor to unpack our kayaks. The trip concludes with a later afternoon transfer to the Friday Harbor Ferry Terminal. Extend your time in the lovely San Juan Islands or begin the journey home. Breakfast and lunch included.

Sea kayaking: 7-10 miles on open water with waves, tides, currents

Itinerary map for San Juan Islands Kayaking – Roche Harbor to Stuart Island

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.

Provided by REI

  • All Group Cooking Gear
  • Dry Bags
  • Group First Aid Kit
  • Paddles
  • PFD and Spray Skirt
  • Tandem Kayaks
  • Tent(s)

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.