San Juans Island Hopper Hike & Kayak - Lodge Based

Trip Length5 Days
Group Size4-12
Activity level
Starting from
$4,199 for REI Members
$4,618 for non-members
DeparturesJun 2025-Aug 2025

Spend five days soaking up the magic of the San Juan Islands on an exhilarating hike and kayak adventure.

Home to a magnificent combination of stunning scenery, quaint villages and diverse wildlife, the San Juan Islands are the pride and joy of the Pacific Northwest. Join us for five amazing days hiking and kayaking through the heart of these beautiful islands. Set out on a premier wildlife watching cruise in search of orcas, Dall's porpoise, harbor porpoise, minke whales, humpback whales and more. Throughout the journey we enjoy cozy, unique accommodations and delicious meals inspired by the region.

By day we hike the best trails on the islands and paddle emerald-green waters teeming with marine life. By night we enjoy fireside meals, soak in private hot tubs and enjoy spectacular sunsets. Along the way our expert guides teach us valuable outdoor skills while offering insight into what makes the San Juan Islands so remarkable.

Unplug along trails surrounded by towering old growth trees.

Trip Highlights

  • Explore the old Royal Marine Barracks and formal gardens of historic English Camp
  • Kayak waters rich with marine life while circumnavigating Henry Island
  • Sleep among the trees in a luxury yurt and relax at a historic Pacific Northwest resort
  • Enjoy 360° views from Mount Constitution, the highest point in the San Juans
  • Search for whales, porpoise and more on a premier wildlife cruise


This trip is rated Easy Active [2]. You should be capable of kayaking up to 8 miles (up to 5 hours) and hiking between 3-8 miles (please reference daily itinerary for specific daily mileage). Beginning kayakers are welcome. You should be at ease in a small boat on the open water and know how to swim. You should also be comfortable spending 3-4 hours on a large boat in open water.

  • Hiking
  • Kayaking

What's Included

Four nights' accommodations; meals as noted in the daily itinerary; tandem kayaks (singles are not available) and kayaking equipment; park or other admission fees; wildlife watching cruise; interisland ferry fares while on trip; all ground transfers as noted on daily itinerary.


Luxury yurts, 2 nights; historic resort, 2 nights

Your Adventure Itinerary

Itinerary map for San Juans Island Hopper Hike & Kayak - Lodge Based
Day 1

Kayak around beautiful Henry Island

We meet this morning in beautiful Friday Harbor on San Juan Island. After a 20-minute van ride to historic Roche Harbor, our guides conduct a kayaking orientation and safety briefing before we hop into our boats. We're then off on a spectacular circumnavigation of nearby Henry Island, which sits off the northwest edge of San Juan Island. Close enough to be beginner-friendly, but remote enough to offer an intimate look at the quiet corners of the archipelago, Henry Island is the perfect intro to our time in the San Juans. Along the way we keep an eye out for the countless species that call this area home, including whales, porpoise, seals, sea otters, bald eagles and more. We wrap up our first day with a welcome dinner at a local restaurant. Lunch and dinner included.

Sea kayaking: 7-8 miles (4-5 hours)

Day 2

Explore English Camp and embark on a world-class wildlife cruise

This morning we hike through the historic outpost of the Royal British Marines: English Camp. We hike a loop trail that features some of the most important points within the camp as well as some incredible views along the water. Later this afternoon we hop aboard a wildlife watching vessel for a world-class tour of the waters surrounding San Juan Island. Famous residents of this rich habitat include whales (orca, minke and humpback), harbor porpoise and Pacific harbor seals. While wildlife sightings are never predictable or guaranteed, with patience and the guidance of our onboard experts, we spend the next 3-4 hours with cameras at the ready for a lucky shot. Should time allow we'll round out our day with a hike to Cattle Point lighthouse, which offers amazing views across the Salish Sea. Dinner will be prepared by our guides, featuring local seafood and a gin tasting from a nearby distillery. All meals included.

Hiking: 1.7-2.7 miles, Elevation gain/loss: +50-75' / -50-75'; Wildlife watching cruise: 3-4 hours

Day 3

Enjoy incredible views from Iceberg Point and Point Colville on Lopez Island

This morning we pack up and depart our San Juan Island accommodations in anticipation of the next leg of our island-hopping journey. First up, we head to charming Lopez Island where we hike to Iceberg Point. Sitting on the far southwest corner of Lopez Island, Iceberg Point offers sweeping views across the Salish Sea to the Olympic Mountains. Here we enjoy a delightful picnic lunch before starting our next hike: to Point Colville on the southeast corner of the island. This delightful loop trail meanders through forest before reaching craggy bluffs with panoramic views across the Strait of Juan de Fuca. Once we've wrapped up our day of hiking, we spend some time exploring tiny Lopez Village before hopping on the interisland ferry to Orcas Island. Our home for the next two nights is the historic Rosario Resort. All meals included.

Hiking: 5.2 miles, Elevation gain: +491'

Day 4

Hike to the top of Mount Constitution, the highest point in the San Juan Islands

After a hearty breakfast we're off to ascend Mount Constitution! A must-do for locals and visitors alike, Mount Constitution is the highest point in the San Juan Islands. At its peak, visitors have the option to climb a stone tower built by the Civilian Conservation Corp in 1930s. On a clear day, views from the top of the Mount Constitution watchtower extend 360°, across the archipelago and beyond. After a full day on the trail we head back to Rosario where we have time to relax before celebrating our last dinner together as a group. All meals included.

Hiking: 6.7 miles, Elevation gain: + 1,500'

Day 5

Enjoy the spray of tumbling waterfalls and the cool of lush green forests

This morning we bid beautiful Rosario farewell before hitting the trail for our last hike on Orcas Island. Our destination is Cascade Falls, which at 40 feet is the tallest waterfall on the San Juan Islands. And while Cascade Falls is reward enough, our route there winds through a lush, green, quintessential Pacific Northwest landscape. Hidden waterfalls and trickling creeks dot a forest filled with towering trees and bright-green ferns. We wrap up our hike with a delicious lakeside picnic lunch, where we reflect on our time together in the beautiful San Juans. From there we head back to Eastsound and the Orcas Ferry Terminal, where we say our final goodbyes. Breakfast and lunch included.

Hiking: 3.5 miles, Elevation gain: +200'

Itinerary map for San Juans Island Hopper Hike & Kayak - Lodge Based

Gear List

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.