Salish Sea Sailing and Sea Kayaking Adventure 

San Juan Adventure 1
San Juan Sailing, hiking, and sea kayaking adventure

Location: San Juan Islands, WA

  • Sailing
  • Sea Kayaking
  • Hiking
  • Trail Running

  • June 8-14, 2022
  • June 12-18, 2022

Cost: $2695 each

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Cost Includes
Sailing Charter, all meals on board sailboat or during sea kayaking trip, PFDs for sailing and sea-kayaking, services of Captain, Sea Kayaking guide, Hiking guide, sea-kayaks and all specialized kayaking gear including kayaks, paddles, spray skirts, and boat expenses such as fuel & moorage fees.
Cost Does Not Include
Transportation to/from Friday Harbor at start and end of trip, personal clothing, alcoholic beverages, guide gratuities, meals taken in restaurants (optional).

San Juan Adventure 2
San Juan Adventure 3
San Juan Adventure 4
San Juan Adventure 5
San Juan Adventure 6
San Juan Adventure 7
Spend a week sailing and kayaking in the Salish Sea as we explore our favorite remote islands in the San Juans. These spots can only be accessed by private vessel and are a hiking and trail running paradise. At night we will anchor in beautiful sheltered bays ideal for paddle boarding with a dedicated tender providing easy shore access. We have chartered Misty Blue Yonder, a modern 45 foot sailboat for our basecamp for the first 4 nights, and will then transition to sea kayaks as we explore the outer islands of the San Juans. This is the maiden voyage for an as yet unnamed adventure travel project we are launching.

The trip begins and ends in Friday Harbor on San Juan Island. Friday Harbor is easily reached from Anacortes by ferry, or by float plane from Seattle, and is central to the islands. This is an active trip that will have us sailing early each morning to a new hiking venue with time built in to give you afternoons and evenings unscheduled so that you can enjoy the boat. No previous sailing or sea kayaking experience is required. We have taken care of the logistics, will cook the meals, and make sure that everyone gets plenty of exercise of each day.

Planned Itinerary 

*Note: Boat life is shaped by the weather and tides, and we will adapt to the conditions to give us the best sailing and hiking each day. While we may do exactly what is listed below, we may also change up the order as needed. We have chosen the time of year with the best weather in the San Juans.

Day 1: Travel to Friday Harbor

Meet the group at 5:00 PM in Friday Harbor and board Misty Blue Yonder. Once on board we will conduct a safety briefing, help you move into your double cabin, and explain how the boat works. We will serve dinner in the spacious cockpit and discuss the plan for the week.

Day 2 -  Sail from Friday Harbor to Patos & Sucia Islands

After casting off in the morning we head for Presidents Channel and Patos Island 16 NM to the NE. This is a good spot to see resident Orcas. Our Captain will need help with the sailing and can bring any interested volunteers up to speed. It takes about 4 hours to reach Patos. The landing here can be tricky due to the current; we will either anchor at the west end of the island or be dropped off with the boat then sitting offshore while we visit the lighthouse and hike the 1.5 mile loop on this bucolic, uninhabited island.

Once off Patos, we depart, grab lunch on board, and swing around the north side of the island where we usually spot Stellars Sea Lions, and have seen Minke Whales as we sail to Sucia Island. The afternoon will be spent exploring Sucia's extensive trail system with participants also free to use the paddle boards to explore the shoreline. We almost always see river otters in the water around Sucia. Dinner will be prepared by the crew as the sun sets. When on Sucia our kids usually insist that we go for a night swim in the bioluminescence that is always present here in the summer.

Day 3 - Sail from Sucia Island to Cypress Island and then Orcas Island. 

In the morning we follow the current east and then south as we use the Rosario “Bullet Train” to travel 13 NM to Cypress Island. Once we land on Cypress we have several hiking options, ranging from 5-8 miles. We will be dropped off on the east side of Cypress, traverse the island and get picked up in Smugglers Cove or Strawberry Bay on the west side. We will then sail across to Orcas Island and tuck into East Sound. On the trip to Orcas it always makes sense to stop for homemade ice cream at the store on Blakely Island. We will spend the night at the Rosario Marina and serve another fine dinner on board. You also have the option to soak in the hot tubs at Rosario Resort's spa or run up to Cascade Lake for an evening fresh water swim.

Day 4 - Sail from Orcas Island to San Juan Island

Rosario is the ideal access point for the 8-12 mile hike of Mt. Constitution, the highest peak in the San Juans. Climbing this mountain will be our goal for the day. If we start from the resort the hike takes 5-6 hours or we can shuttle up to Mountain Lake and turn this into an 8-mile loop. The hike takes us up through the old growth forest of Moran State Park, and is about the most pristine section of old growth we have seen in Washington. Most of the old growth in the San Juans was cut to fire the lime kilns on San Juan Island, but this parcel was preserved by Seattle shipbuilder Robert Moran and then later donated to the State of Washington. The summit is a majestic place with views of Mt. Baker towering to the east. It the afternoon we can hit Buck Bay Bistro and pick up some locally harvested oysters, clams, & dungeness crab for dinner before the 2-3 hour sail back to Friday Harbor. We will spend the night onboard in Friday Harbor and get ready for the start of our kayaking adventure the next morning.

Day 5 - Paddle from San Juan Island to Stuart Island:

In the morning we meet our guide from Outdoor Odysseys and get outfitted for sea-kayaking. We will launch from the west side of San Juan Island after loading our double kayaks with 3-days food and camping gear. The guide will provide a thorough briefing covering paddling technique, safety, and boat handling. We won’t head out until everyone feels comfortable with maneuvering their boat. We then paddle north along the Haro Straight with views west to Canada's Gulf Islands. This is one of the prime spots in the San Juans to view salmon and Orcas and follows the rugged shore of San Juan Island. After a few hours we will take a break while the guide prepares lunch and then cross Spieden Channel to Stuart Island. We camp in Reid Harbor tucked among madrone, cedar, and douglas fir. Sit back and relax with a glass of wine while your guide prepares a gourmet meal.

Day 6: Circumnavigate Stuart Island or paddle to Jones Island:

We will spend the first half of the day circumnavigating Stuart Island while exploring its coves, beaches, and stunning headlands. This remains prime territory for spotting whales and always brings us Bald Eagles, seals, and a variety of interesting sea birds. Once done with the paddle you have the option to hike to the one room schoolhouse or all the way out to the light house.

Alternately we can use this day to move over to Jones Island and stay in the beautiful little campsite reserved for human powered vessels and hike on the trails of this island. Jones is unique because it is home to one of the only cacti that grows in western Washington thanks to the rain shadow created by the Olympic Mountains. There is also a grove of Garry Oak, native to the Islands, but increasingly hard to find. The guide and the group can decide if it makes more sense to circumnavigate Stuart or paddle to Jones, which puts us closer to San Juan on the last day.

Day 7 - Paddle from Stuart Island to San Juan Island

After a hearty breakfast we will begin the return trip to San Juan Island. A favorite stop along the way is Jones Island, with a good hike, if we have not already moved here the day before. After one last artfully prepared lunch we will arrive back on San Juan Island where we will load our gear and have you back in Friday Harbor between 3 and 4 pm. Catch the ferry back to Anacortes or continue your adventure in the San Juans.

The Boat 

Misty Blue Yonder is a 4-cabin sailing sloop, with 2 heads & 2 showers, a full galley, a spacious salon for eating and relaxing, and a nice swim platform for swimming off the back and easy access in and out of the dingy. We will have a dingy equipped with an outboard engine for getting to and from shore. This ship has an ideal layout for multiple couples or 2 families and is a charter boat maintained by premier local company San Juan Sailing. She also has a comfortable cockpit that provides plenty of room for outdoor dining. We will equip her with paddle boards and fishing gear for anyone with a license who wants to target in-season fishing.

Suntime Charters 

Colin Sternagle is a US Coast Guard Licensed Captain and runs Suntime Charters with his wife Ariahna Jones. Colin will be in charge of the sailboat. PNW born and raised, he teaches sailing for San Juan Sailing and Charters, was our sailing instructor, and had been a key consultant as we focus on projects on our own boat. John & Olivia know Colin and Ari from Olivia’s time spent working for Orion Expeditions where John & Olivia first met.

Outdoor Odysseys 

Tom Murphy is a sea kayaker with a skiing addiction. A longtime guide for Outdoor Odysseys, Tom purchased the company in 2012, and runs an exceptionally well organized kayaking program know for its great food & friendly vibe. He works like a dog in the summer and spends his winters skiing in Washington, Canada, and Japan. We should expect a visit from Tom in his restored 1950s Chris Craft ski boat.

Why are we running this trip instead of climbing or ski touring? 

Many years ago John guided a ski trip to the Antarctic Peninsula aboard a large retrofitted science vessel. On that trip he noticed a small sailboat also in this incredibly remote area for skiing. This gave him an idea that led to a trip 6 years later when he sailed 850 NM in the South Atlantic from the Falkland Islands to South Georgia Island on the Pelagic Australis with legendary skipper, Skip Novak. Skip, John, and Dave Hahn led a small group on a successful ski traverse of South Georgia following the route that Ernest Shackleton took in 1916. From here his interest in sailing grew and we now own a sailboat that we have been using to explore the San Juan Islands.

Over the past 2 summers we have spent the better part of the summer exploring the San Juans and building our sailing resumes in hopes of moving onto a larger boat capable of taking us to high latitudes safely, with our kids on board. On these trips we often find ourselves ending the day and chatting with Tom and Colin about how we could combine all of our skills into a compact adventure for our collective customer base. We decided this winter to pull the trigger and committed to a solid charter boat and put together a great team to make it all come together.

Do I need previous sailing or sea kayaking experience?: 

No. You should have decent fitness and be able to paddle for 4-5 hours per day and the hiking can be scaled up or down depending on personal desire. We recommend that paddlers be at least 12 years of age and younger paddlers will be paired with a parent in a double kayak. Trail runners will find this an ideal venue for long runs on pristine trails with a nice ocean breeze. Don't trail run? We can hike while the others get after it.

Am I going to get seasick? 

The San Juans are relatively protected from swell and as such we have not experienced much in the way of sea sickness while sailing here. If we head into the Straight of Georgia in high winds (optional) it is possible, but with basic precautions taken it should not be an issue. Knock on wood, but we have not gotten sea sick in the past two summers and we average 8-9 weeks out each summer.

How do the sleeping quarters work? 

The boat has 4 double cabins. Each sleeps 2 people comfortably, but is best shared by couples, families, or close friends. We are planning to have 6 guests. There is a higher rate for singles looking to have their own cabin. In a pinch we could squeeze 2 families of 4 on board, which would leave the Captain and the First Mate (John or Olivia) to bunk in the salon and/or the cockpit. If the weather is good you are free to sleep on the deck, which is quite large.

What gear do I need? 

Most of the gear that you take sailing can be used for the sea kayak leg. We will have bedding for the boat, but you are also free to use your sleeping bag for both the sailing and the sea-kayaking. We provide things you may not own like PFDs (lifejackets), spray skirts, and all of the specialized gear such as the boats, paddles, and such. On our boat we usually wear running shoes and/or flip flops and have found that all of our mountain gear works perfectly well for sailing. We will send you a detailed equipment list upon registration, but if you already do things outdoors you probably own everything you need.

What is the vibe we are aiming for? 

We love to sail and we love to get exercise. The goal of this trip is to make sure everyone gets to experience life on the water and gets as much aerobic activity as they want each day. Need to run 6 miles daily to be happy, that can easily be accomplished. We also realize that this is your vacation and have built in time for people to simply relax and soak it all in if that is what sounds appealing.

Add-On Trips 

Have more time before or after the trip and want to do some climbing? June is the perfect time of year to come over to Leavenworth for some rock climbing or head up to Mt. Baker for either a summit climb, a mountaineering course, or both. Drop us an e-mail if you would like to build out a bigger trip. The San Juans are also excellent for road biking if you want us to help connect you with some tour ideas on the ferry accessible islands, all of which have miles or excellent paved roads that can be combined into impressively long rides.