San Juan Islands Multisport

Trip Length 6 Days
Group Size 4-13
Activity level
Starting from
$3,399 for REI Members
$3,679 for non-members
Departures Aug 2022-Sep 2023

Scenic hikes, panoramic views and plenty of adventure; this 6-day trip is a gem for lovers of the island life.

Washington's spectacular San Juan Islands are a nature-lover's paradise. Great snowcapped peaks rise all around as scores of marine mammals and shorebirds bask on the craggy coastline. Whales and dolphins feed in the protected waters while hikers, cyclists and paddlers enjoy the gentle pace of island life.

Our journey highlights the best of the San Juan Islands. Take scenic hikes to panoramic views of the surrounding islands and peaks, and bike the quiet back roads of Orcas Island to reach the highest peak in the San Juans. Kayak in search of seals, sea lions, porpoise and more. Enjoy an unforgettable whale watching tour on one of the islands' most environmentally friendly boats as we search for the Orca whales that call the area home. Dine on locally-sourced, organic meals prepared fresh daily by our guides throughout the trip. Each evening, we indulge in deluxe camping and lodging conditions under the starry Pacific Northwest sky.

This is a great trip for adults and fit, older teens. If you're traveling with younger children, check out our San Juan Islands Family Adventure.

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

Trip Highlights

  • Get a taste of island life while hiking, kayaking, and cycling the San Juans
  • Enjoy an overnight kayak tour, local farm visit and whale watching excursion
  • Dine on fresh, locally-source meals and stay at a lovely mix of accommodations
  • Relax among snowcapped peaks, bountiful islands and beautiful beaches


This trip is rated Moderate [3]. Beginners are welcome - it is not necessary to be an experienced kayaker although it is beneficial to have had some previous kayaking or canoeing experience (prior camping experience is also a plus but not mandatory). You should be at ease in a small boat on the open water and know how to swim. A typical day will consist of 3-4 hours of activity (paddling or hiking) with occasional breaks for sightseeing, wildlife viewing and meals. Participants should come equipped with a spirit of adventure and willingness to pitch-in and help with camp chores when necessary.

  • Cycling
  • Hiking
  • Kayaking

What's Included

Five nights accommodations; camping permits and associated fees; all meals as noted in the daily itinerary; group camping equipment (tents, sleeping bags/pad, cooking gear, utensils, etc.); tandem kayaks (singles are not available) and related equipment; dry bags; bikes and bike helmets; whale watching cruise on Day 5.


Furnished canvas tent-cabins, 2 nights; Island camping, 1 night; Outstanding lodge or cottage accommodations, 2 nights

Your Adventure Itinerary

Itinerary map for San Juan Islands Multisport
Day 1

Welcome to Friday Harbor; sea kayak the north end of San Juan Island.

Our trip begins today in Friday Harbor, Washington, located in the San Juan Islands archipelago. Meet your guides and fellow travelers at 12pm at a park next to the Friday Harbor Ferry Terminal. We transfer to Roche Harbor for lunch, followed by a kayak trip to take in the sights along the northern tip of the island. We learn how everything in the islands is interconnected, from kelp to jellyfish, seals to orca whales. Watch for seals, shorebirds, porpoise and more as we get a feel for paddling. After our introductory paddle, we return to Roche Harbor and get outfitted with bikes and helmets for the next day’s excursion to Orcas Island. We then check into our comfortable canvas tent cabins at Lakedale Resort. Tonight’s dinner, made with locally sourced ingredients, in prepared by our guides. Lunch and dinner included.

Sea Kayaking: 5 miles (3 hours) on open water with waves, tides, currents.

Day 2

Cycling to Moran State Park and Mount Constitution on Orcas Island.

We have an early start to ferry from Friday Harbor to Orcas Island. Our support van, with bikes loaded on the trailer, accompanies us. Today we cycle to the Eastern Lobe of Orcas Island, following a route that meanders through Crow Valley, past family farms and tidy orchards. Depending on timing and weather, we have lunch in Eastsound or at Cascade Lake in Moran State Park. From Cascade Lake, ambitious riders may choose to bike to the summit of Mount Constitution (2,409’), the highest point the San Juan Islands. At the top, we enjoy 360-degree views of the surrounding islands from a stone watchtower. Returning to San Juan Island by ferry, we transfer to Lakedale for dinner and discuss preparations for our kayaking trip to Stuart Island. All meals included.

Cycling: 13-15 miles. Optional ride up Mt. Constitution (no option to ride down): 5.4 miles, up to 15% grade, 2000’ climb. Paved roads with some rolling hills and one very steep section.

Day 3

Sea kayak to Stuart Island to camp and hike to Turn Point Lighthouse.

Following breakfast, we transfer to Roche Harbor, pack our dry bags into tandem kayaks and begin our paddling trip to Stuart Island. We head into Spieden Channel to explore the shorelines of Spieden and Sentinal Islands before reaching Stuart Island. We set up camp at Marine State Park, which has primitive sites with picnic tables, fire pits and composting toilets. There is time to relax in camp, or we stretch our legs on a hike to Turn Point Lighthouse. This is among the most scenic overlooks in the Pacific Northwest! The guides prepare dinner and share the history of the area over a campfire. All meals included.

Sea Kayaking: 7-10 miles (4-5 hours) on open water with waves, tides, currents. Hiking: 5 miles (3 hours).

Day 4

Paddle back to San Juan Island through protected wildlife refuges.

We pack our gear into our kayaks, then paddle across Spieden Channel towards the north side of San Juan Island. We watch for eagles, seals, porpoise and orca whales; much of the saltwater and shoreline in the islands is a protected wildlife refuge so sightings of birds and mammals is a regular occurrence. Following the coastline, we peer into tide pools to find invertebrate and plant life. A picnic lunch on a remote beach provides fuel for our return to Roche Harbor. Arriving in the mid-afternoon, we unpack our kayaks and transfer to Lakedale Resort. The next two nights are spent in log cabins, or we stay in rooms at the lodge. The guides prepare another outstanding dinner. All meals included.

Sea Kayaking: 10-12 miles (4-6 hours) on open water with waves, tides, currents.

Day 5

Take a whale watching cruise or hike the south tip of San Juan Island.

We board one of the most environmentally friendly boats in the islands to view the diverse marine life that surrounds us. In the company of an expert naturalist we look for orca whales, humpbacks, porpoises and more. Anyone not wishing to go on the whale watching tour can join the guides for a scenic hike around Mt. Finlayson and Jakle’s Lagoon. The trail, located on the southern tip of San Juan Island, meanders through grasslands and forests of Douglas fir, hemlock and cedar to the driftwood covered beaches of the lagoon. After the hike or whale watching cruise, we reconvene for a tour of some very special local farms to learn about sustainable agriculture in the islands, how to raise Alpacas for wool, and how to cultivate fragrant lavender. Returning to Lakedale, we enjoy dinner and an evening of relaxation. All meals included.

Boat cruise (4 hours) or hiking 3-5 miles (2-4 hours).

Day 6

Enjoy a final paddle or hike before returning to Friday Harbor.

Packing up, we transfer to Roche Harbor for a sea kayaking excursion around Henry Island to English Camp on San Juan Island. English Camp is a National Historic Park, created after the United States and Great Britain nearly went to war over possession of San Juan Island in 1859, the crisis ignited by the death of a pig. Those not wishing to kayak can hike with a guide up Mount Young (646’) to enjoy views of Vancouver Island, the Olympic range and the Gulf Islands. Continuing the hike we reach English Camp, where we gather as a group for a picnic lunch. The trip concludes with a transfer to the Friday Harbor Ferry Terminal. We plan to arrive by 4pm. Departures by float plane or ferry can be booked for any time after 5pm. Breakfast and lunch included.

Sea Kayaking: 4-6 miles (2-4 hours) on open water with waves, tides, currents. Hiking: 3 miles (2-3 hours) with 600' elevation gain/loss.

Itinerary map for San Juan Islands Multisport

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.

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.