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I love the fact that I can take my home on adventures.  Sailing through the San Juan Islands and dropping anchor at a beautiful destination for the night is something I feel fortunate to be able to do. After buttoning everything up on the boat, I usually lower a small river kayak down to the water from the fore-deck and then paddle to shore to walk trails, sit on a beach, or hit a local store if available.  The kayak is really meant to be on rivers, it doesn’t track that well on flat water, nor does it cut through waves well – but it gets me to shore and back in a passable manner.  Back on my boat, I’ll cook dinner and then read and relax before calling it a night – the water lapping at the sides of my boat and (hopefully) some gentle rocking lulling me to sleep like a baby in a cradle.

At anchor in ‘Cimaise’ off Spencer Spit.

But I’ve felt a growing disconnect for some time. Mid-September found me standing on the northern shore of Cyprus Island and looking out at my sail-boat which was bobbing up and down – tied to a state park mooring ball.  Curious about a couple odd looking ~12ft sailboats that were pulled right up on the beach – I ended up speaking to two women who were camping nearby. They had recently arrived in these small sailboats called ‘Pelicans‘, unloaded their gear and set up camp.  I relayed that in my former life I hiked a lot and prided myself on carrying minimal and ultra-light gear, that I loved my sailboat but that I felt like I was driving a motor home and staying in aquatic KOA campgrounds.  They laughed and said that if I wanted to carry the analogy further they were car-camping with their Pelican sail boats.  And then they pointed to some sea-kayakers who had just glided up, ‘And those people are back-packing.‘ Their words echoed in my ears. Even though I liked the feeling of the wind pulling me along and having a lot of amenities on my sailboat – I have been feeling increasingly detached from the coasts I am traveling along with a boat that needs at least seven feet of water,  rendering many small coves and inlets impossible.

So when my friends Kimberly and Benj invited me a couple weeks later to go on a multi-day sea kayaking trip with them I did not hesitate.  Both are experienced ‘outdoor folks’,  versed in adventure races, kayaking, pack-rafting, and back-country skiing to name a few.  Kimberly has also been working through a full sailing curriculum and developing skills in marine chart reading and navigation techniques.  They had an extra kayak to lend and had already studied the tides, currents, and wind conditions and plotted a route.  And the start would be near my home town of Anacortes, WA. In other words, all the hard work was done and all I really had to do was show up. As Kramer would say, ‘Giddy Up!’

Kimberly and Benj on Spencer Spit, Lopez Island.
Rosario Strait – Wikipedia

We decided to get a jump on things by taking our kayaks on the ferry to Orcas Island from the terminal just west of Anacortes on Fidalgo Island – the goal included a safety step, allowing us to skip a potentially rough crossing of Rosario Strait – a tough body of water encompassing shipping lanes that route some pretty large commercial boats north to Canada and Alaska.  We met Megan and Ross, two of Kimberly and Ben’s friends at the ferry terminal and started sorting gear out – thankful that the ferry was running a little behind schedule.  Getting our kayaks on to the ferries required a little finesse, greatly aided by a having some small wheels to strap under each kayak.






Boats in a boat. Heading to Orcas Island on the ferry.


The ferry ride went quick and with a little more fussing near the landing on Orcas Island, we had our boats in the water and we were off to the races.  Benj had lent me a pretty fast fiberglass kayak – this was almost ten feet longer than the little river kayak I keep on my sailboat for getting to shore. It had lots of room for carrying gear, and foot pegs attached to a rudder that could be dropped down. I decided to try paddling without the rudder and found that with a little effort I could keep a relatively straight line and almost keep up. I still have some work to do with my technique, or possibly I am just lazy – for most of the trip I was a laggard but never by too much (or else the group was simply being kind and slowing down occasionally so I could catch up). Overall,  we were lucky,  conditions were really calm and without much effort we were covering ground at 3-4mph headed toward Spencer Spit on Lopez Island.  The area was not new to me – but seeing it from a sea-kayak and moving through it largely under human power was new.


Playing keep up while minding the ferry traffic.

After a few hours of paddling we reached one of my favorite places in the islands: Spencer’s Spit – a long stretch of sand sticking out into the water on the east side of Lopez Island.   During the summer, I would often tie up to a mooring ball on the north side of the spit and go ashore to stretch my legs, walking a loop trail that went past a campsite reserved for people arriving solely under human power. The campsite was part of the Cascadia Marine Trail, a 150 mile water trail starting further south in the Puget Sound. There was some pretty explicit writing on the sign at the campsite that paddling ashore from a moored boat did not constitute ‘arriving under human power’ – but this time I was legit.  We pulled our boats up high above the tide line, ferried our gear a couple hundred yards up to the site and had a great evening.

All done for the day – kayaks above the high tide line


Looking out the south side of the spit toward Thatcher Pass

The morning of the second day of paddling brought a low tide and calm waters again. We headed back north – mindful of crossing the north-south ferry route and the seals that were checking us out.

Tide is out! Getting ready to leave Spencer Spit.


Kimberly checking a compass bearing before leaving Spencer Spit

Just as we reached Obstruction Pass Park – we met up with two more friends Emma and Greg. Now numbering seven, we caught the current running east through Obstruction Pass and then paddled a couple miles north to Doe Island, a tiny dot on the east side of Orcas Island. I had sailed by it before without too much thought, but it turned out to be a gem with some really great campsites facing Rosario Strait.

I took the southern-most site and spent a couple hours reading and dozing in my hammock before everyone sat down to eat dinner together. While swinging back and forth, I finished the book ‘The Sun is  Compass‘ (non-affiliate link to independent bookshop) about a couple who paddled and trekked ~4,000 miles from near this area to Alaska.  I highly recommend the book , especially for bird lovers as the writer, Caroline Van Hemert, is an ornithologist.. Reading about their epic journey, along with this relatively brief experience in the Salish Sea has kindled some dreams.  Sadly no sunset as we were facing east, but still a beautiful night with some good company.

Reading and dozing


Dinner on Doe Island


On the third day, we woke to the sun coming up over Lummi Island and the ragged bumps of Cyprus’s ridge line. Kimberly, Benj and I were going to paddle back to Anacortes, crossing Rosario Strait finally and hugging the west side of Cyprus Island as we headed south. The others had more time and were going to continue north to Clark Island for more adventure.

The meandering ridge line across the water is the west side of Cyprus Island – about 3 miles away and our first goal for the day.


Breakfast of champions – At Kimberly and Benj’s camp spot on Doe Island.


After we had everything packed up, we said goodbye to the rest of the crew and headed east, crossing three miles of open water – essentially cutting directly across Rosario Strait and a major shipping lane that routes traffic north to Vancouver and Alaska. The first part of the paddle was idyllic – the water was calm and it felt like a perfect early fall day on the water.


Benj taking a moment  – my favorite picture from the trip.

Later, as the coast line of Cyprus Island loomed closer and offered sanctuary from potential shipping traffic, we had a few tense moments trying to decide whether we could outrun a tug pulling two huge shipping containers (we decided to wait – which is probably always a good call but a hard one to make when you are loitering in the northbound shipping lane).  The picture below doesn’t really do it justice – tugs that look like tiny specks in the distance can be in front of you before you know it. And when they are pulling huge barges and you are in their way, no one is particularly happy.


A tug pulling not one, but two (!) barges – Benj waiting for the traffic to pass. Fortunately not much other traffic.


After the tug and barges passed us, we started paddling for the west side of Cyprus, letting the current pull us a little to the south before finally pointing our boats straight south and running with the current toward Strawberry Island near the southern end of the island.

Safely heading south along Cyprus – closing in on Strawberry Island.

Of course I don’t have any closing images of our final arrival at Washington Park near where we initially boarded the ferry three days prior. Let’s just say it was a nice beach, filled with families enjoying one last summer picnic. And us, pulling our kayaks ashore with smiles. Maybe you can close your eyes and imagine.

What did I learn on this trip?  a) I want to buy a sea kayak! Ideally something really light weight (30 pounds would be ideal) with water-proof hatches that are large enough that I can easily fit dry bags with my gear into the compartments.  I don’t want tiny little hatches.  b) Likewise – I need a large cockpit. My knees are pretty messed up at the moment (another reason to get more into paddling) and trying to double up my legs to get in and out of the kayak is hard. c) I don’t need a rudder. I’ve heard they can add up to 5 pounds to a kayak.  Maybe I’ll learn that there is a really good time to have one and I will change my tune.  d) I want to learn more about sea-kayaks with out-riggers and sail kits.  It seems like the perfect combination but I’m also a bit skeptical how well it really works.  e) I need better core strength. This goes for pack-rafting too – both ask the paddler to sit straight up in their seats. But I’m a sloucher and thus a less efficient paddler. f) I’m going to need to figure out a good system for carrying a sea-kayak on my boat and also on my van. g) Given that I’m still new, clumsy, cheap and can be known to trash gear easily – buying a plastic kayak instead of fiberglass might be a wise starting point. e). I’m interested in someday trying to do a human powered journey to Alaska.

Big thanks to Kimberly and Benj for having me along on this trip and showing me the ropes.  That was fun.  I’m writing this a week later from my parents house on the bank of the West Branch of the St. Regis River in northern New York. I just had a great conversation with neighbor Larry about paddling opportunities around these parts as well as in the nearby Adirondacks. It’s been a little over 4 years since my first and last canoe trip in the Adirondacks. An experience that I often revisit in my mind – wishing it had continued.  This time,  I hope to at least dip a paddle in the water before heading back to Anacortes for some serious sea-kayak shopping. Or maybe a Pelican sailboat. Or maybe an Angus Expedition Rowboat with a sail kit. Or maybe a kevlar canoe. Or maybe all of the above. One can dream right?


October 1, 2022
Camp High Skies – Parishville, New York.


Approximate Paddle Route

6 thoughts on “Paddling from Orcas Island to Anacortes in the San Juan Islands

  1. This sounds and looks great! Great post–enjoyed reading this. Its been a long time for me, but many of your experiences reported here resonate with the few overnight paddle trips I’ve done in the San Juans. Especially the comment about watching the traffic and holding up, even though they look like specks initially. I’ve launched from WA Park–think I told you. I’d like to get out there again. A lot to be said for those plastic boats–I’ve used those up around Bham. Nice for bumping into things.

    1. Hi Scotty – I was thinking about you out there – a story you told me about waiting to leave Cyprus I think due to the tide. Tricky waters literally and figuratively. Benj just sent me a link to a plastic boat on Craigslist. I’m still in NY but maybe when I get back….will touch base with you then too. – Seth

  2. Quite a feat, Seth. You never cease to amaze me. Hope your Mom & Raphael are doing well. I thought of them recently while on a AAA Bus/ Cruise trip Akron, Niagara Falls, Toronto, Ottawa, Montreal, Quebec, NH, VT to Boston; then Bar Harbor, Halifax, St. John, Portland and back to Boston. Just no time to get off to see them. Cell phone was crappy… oh well. Hope to get up to see them sometime. Wishes of continued success and good health on your journeys. Pictures were beautiful, too.
    Arne Hosbach

    1. Thanks Arne for the read and the comment and the sentiments! Sounds like quite the trip you were on! Love to family and stop by if you are ever in northern WA! -Seth

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