5-Day Kayak Expeditions

Friday Harbor to Anacortes

Here it is—your bucket-list kayak trip through the San Juan Islands of Washington State. You’ve shopped around, and now you know this is the only expedition of its kind—a one-way journey through the islands. You want something special. Something different from all the rest. No backtracking, a new campsite every night, onward and forward!

This trip covers almost everything that needs to be seen in the San Juans. You’ll kayak through the beauty of the western San Juan Islands, witness the perfect sunsets in the Wasp Islands Group, and plot a course right through the heart of the San Juans while camping at Marine Parks. The wild shorelines of the San Juan Islands, with their dense wildlife populations, beckon you. You’ll never view the islands in quite the same way again.

← All 5-Day Trips

May - October 11

All Inclusive: $1299 | Self-Catered: $1149
Prices are per person, based on double occupancy, 4-person minimum. **Single occupancy, private tent: $50 fee. More Info: Rates & Schedules

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  • All-Inclusive
  • Self-Catered

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By kayaking along Haro Strait, through the Wasp Islands, and into the Cypress Island Marine Reserve, you spend significant time in the wildlife hotspots of the San Juan Islands. Exciting marine animal encounters are a possibility all along this route, as are porpoise sightings, sea lions, and the densest population of harbor seals on the planet. Bald eagles nest on nearly every island you explore, and sea birds are everywhere.

By selecting the 5-Day trip from San Juan Island to Anacortes you are choosing a one-of-a-kind experience. No backtracking, new campsites every day, and the opportunity to see more wildlife than on any other sea kayaking trip in the San Juan Islands.


From start to finish you will get to see the entire archipelago as the quaint pastoral landscape, dotted with beautiful seaside homes, gives way to the heavily forested and more mountainous landscape of the eastern San Juan Islands. With its glacier-covered volcanic peaks, Mount Baker appears suddenly through gaps between islands and provides one of the most dramatic landscapes in Washington State. Each night, your island campsites offer a slightly new sunset and a brand new perspective of this lovely island group.

Delicious Cuisine

Our hope is always to exceed your expectations regarding the food we serve. We understand that the one thing that you are sure to remember is whether the food was enjoyable. On our tours, you won’t go hungry! As the company's owners, we see to the creation of each meal plan on our multi-day camping expeditions. We source most of our food from local organic farms here in the Skagit and Samish River valleys and use the freshest seasonal ingredients possible in all of our dishes. On our 5-day trips, we often make a quick stop at little stores found on certain islands to replenish our stocks and support the communities there. This allows us to offer the freshest meals throughout the excursion. If you have any special dietary needs, then just let us know, we can accommodate almost any request.


This is an authentic kayak expedition camping experience! Once you depart from San Juan Island you will be entirely self-sufficient, carrying all you need in your kayaks. Your campsites are all in peaceful marine parks and offer splendid views right from your tent. Due to the dry climate of the San Juan Islands, there is not enough water for showering, although many provide potable water. There is no electricity at these campgrounds and so we recommend bringing an external battery for your electronic needs. Washington State Parks operates well-maintained toilet facilities at each camp area.

No Experience Necessary!

Like all of our kayak tours, this one requires no previous paddling experience. Because we depart from San Juan Island the first day can require longer paddling distances. If you wish for a less ambitious itinerary then please let us know at the time of booking so that we can discuss the different options available.

What is included (Fully Catered Package*)

  • Professional guiding service.
  • All of your kayaking equipment (boats, paddles, lifejackets, dry bags, etc).
  • All meals (from lunch on day one to lunch on day three) plus snacks, hot drinks, and limited cold drink mixes. Please feel free to bring your alcohol of choice.
  • Cooking Equipment.
  • Complimentary insulated travel mug to take home with you afterward!
  • All camping equipment, including tents, and insulated Thermarest sleeping pads.
  • All land use permits/fees.
  • Complimentary transportation to the launch site on San Juan Island.
  • The best customer service support in the industry.

Please check our packing list carefully to ensure you have the appropriate gear. If you plan to bring any of your own equipment, then please let us know before arrival so that we do not bring unnecessary duplicates.

*Self-Catered package includes everything above, except food, cooking equipment, travel mug, and camping equipment. This is a great option if you already have your own camping gear and want a budget-conscious choice.

What is not included:

  • Flights, airport transfers, taxis, transportation to launch site.
  • Travel/Medical insurance.
  • Alcoholic beverages.
  • Sleeping bags.
  • Rain Gear.
  • Personal Items (toiletries, clothing, headlamps, etc.).

Sleeping bags can be rented for $35/trip. Please reserve these in advance to ensure that we have one ready for you. They can also be reserved at the time of booking.

About The Area

You will gain quite an appreciation and understanding of the labyrinthine waterways of the San Juan Islands on this trip. Choosing a one-way itinerary allows you to cover new territory with every stroke of the paddle, unveiling new shorelines that you otherwise would be unable to explore on just one trip.
Starting on the west side of San Juan Island, you will be kayaking along the Canadian Border. The body of water here is called Haro Strait, which has a storied geopolitical history. It is a significant waterway due to the presence of the international border between the United States and Canada, a border created in 1872 after an interesting military situation on San Juan Island known as the Pig War.
The trip will also traverse the wildlife-rich waters of Wasp Islands Group, a cluster of nine little islands that are mostly undeveloped, supremely beautiful, and have attracted sailors and visitors for over two hundred years.

Traveling through the heart of the islands allows you to be in the most protected waters of the San Juan Islands. You’ll float past beautiful historical farms and private vacation homes, and the San Juan Island ferries will often be in view as they carry islanders and visitors to their various destinations.

On the last days of your trip, you will enter the islands of Rosario Strait, the principal waterway in this part of the San Juan Islands. It is a hotbed of activity for many kinds of wildlife. There are many National Wildlife Refuges here, and the Cypress Island Reserve with its unbroken forested slopes dominates the scene. The abundance of seals and porpoises on this side of the San Juan Islands is the likely cause for the recent explosion in sightings of transient orca whales here. Keep your eyes peeled for whatever the day brings.

Five days of travel, ever-changing scenery, and no reason at all to backtrack. There is a good reason why this is becoming the most popular 5-Day kayaking trip in the San Juan Islands!

Is this for you?

We specialize in small group, all inclusive, multi-day sea kayak trips in the San Juans.

  • On these multi-day sea kayaking expeditions we strictly adhere to a 6 guest per guide ratio.
  • All trips larger than 6 people will have two guides.
  • Groups of 6 or more guests can choose to have a private kayaking experience! (multi-day trips only)
  • A small sea kayaking group can move much more efficiently. We need less time attending to logistical issues like setting up or breaking camp and have more time for exploring and having fun in the San Juan Islands.

The longer multi-day sea kayaking expeditions are best suited for folks in reasonably good shape. Occasionally there is a need to make a long push to get to the next campsite and we would not want to wear anyone out on a long crossing. We actually design these trips to be a little more physically involved. 5 day trips might average 8-10 miles per day paddling.

Anacortes Kayak Tours reserves the right to change or cancel available departure dates and prices. Once you book a kayak tour with us we will run it, as long as weather conditions permit us to conduct a safe sea kayaking excursion.