Paddles, Pedal & Paint, Part 2: The Ultimate Kayaking Trip to the San Juan Islands
- Wandering with Jodi
- Aug 27
- 9 min read
I paddled, I laughed, I painted—and I somehow managed to keep up with 15 fellow kayakers without capsizing once. (A personal victory worth at least one slice of celebratory pie.)
Note: If you’re wondering how I wound up here in the first place, you’ll want to backstroke over to Part 1, where the “epic trip planning” chaos lives.
After a flight into Seattle, a shuttle to San Juan Island, and a check-in at my hotel, it was time for the mandatory ritual of exploring Friday Harbor—the kind of cute, walkable town where you start to wonder if you should just move there and become a full-time lighthouse painter.
Of course, the moody Seattle clouds hitched a ride with me and hovered over the island like uninvited guests. Sunshine made a few half-hearted attempts to peek through, while my weather app tried to give me heart palpitations with talk of an “atmospheric river” set to crash into Day 1 of paddling. (Yes, I checked the forecast roughly 5,000 times. No, it never reassured me.)
Still, there was exploring to do. After wandering in and out of
charming little shops, I followed my stomach to Downriggers, where I perched on the patio overlooking the marina. Calamari? Ordered. Clam chowder? Absolutely. A deliciously indulgent drink? Don’t mind if I do. Watching the boats sway in the harbor while sipping chowder felt like I had already won the trip.
Stuffed and happy, I waddled back to my home base at Earthbox Inn & Spa, where I attempted to channel my inner responsible adult and get some sleep. After all, four days of kayaking and camping awaited me—preferably with more paddling than panicking.
Day 1: Launch Day
The morning began with a short stroll through Friday Harbor, but not before I made a strategic pit stop at The Salty Fox for a chai latte. (Because if I was going to be swallowed by an “atmospheric river,” I was at least going to do it caffeinated.) Thankfully, the skies were holding back—for now.
Soon, the vans arrived, loaded with kayaks and our two trusty guides. After quick introductions and a round of nervous-but-excited chatter, we tossed our gear aboard and headed off to San Juan County Park, our launch site.
Once there, the ritual began: unpacking, re-packing, and wrapping everything in more layers of waterproof protection than a burrito in tinfoil. We were each given two dry bags—a dainty 10L and a monster 30L—plus plastic bags for sleeping gear in case the forecasted deluge decided to live up to its name. (Spoiler: it did.)
Before hitting the water, we did the classic “dry run” kayak sit test—climbing into boats on solid land to adjust our foot pegs. For those sitting in the back, this was critical. Steering was their sacred duty, and no one wanted to discover mid-paddle that their legs didn’t reach. Life vests and skirts on, safety briefing delivered (a cheerful explanation of what to do if you flip into 41-degree saltwater), and paddles in hand—we were officially sea kayakers.
We set off knowing our first stop—lunch—might also be our last. The atmospheric river was creeping closer, promising rain, wind, and seas that were less “serene postcard” and more “washing machine.” And sure enough, not 10 minutes into our paddle, the skies opened. But despite the rain, the winds stayed calm, and we were rewarded with sightings of eagles, porpoises, and even pink salmon doing acrobatics beside us. Our route hugged the shoreline until we reached Turn Island, about 3–4 miles from launch.
There, the guides made the call: this was camp for the night. We caught a blessed break in the downpour, enough time to pop up our tents while the guides whipped up lunch. The rest of the day became unexpectedly cozy. Under tarps strung through the trees, we shared wine, hot chocolate, and tea, while laughing, chatting, and taking our first watercolor lesson with the travel paint kits provided. A few of us explored the island during another dry spell, where the view of the main San Juan Channel made it crystal clear why our guides had stopped us—whitecaps and howling winds looked more like a scene from Deadliest Catch than a vacation.
Evening rolled in with a hearty dinner, more watercolor doodles, and yes, more wine. Then it was off to our tents, where the rain performed its drum solo all night long. To my great relief, my little backpacking tent—with its trusty rain fly—kept me snug, dry, and dreaming of sunshine.
And wouldn’t you know it? By morning, the storm had moved on, the skies had cleared, and the sunrise promised us a fresh start for Day 2.
Day 2: Sunshine, Channel Crossings & Island Heaven
The day kicked off with the smell of hot coffee and a camp breakfast so good it made me briefly wonder if we should just keep our guides forever. Fueled and happy, we packed up camp, wrangled our gear back into the kayaks, and slid into the water. Destination: Jones Island.
The sky had mostly turned blue, the sun was out, and the mood among
our little kayak fleet was pure joy—even when we had to cross the San Juan Channel and it felt like we were playing an extreme sport called “kayak vs. giant motorboat.” Spoiler: we lived to tell the tale.
The wildlife didn’t disappoint either. Bald eagles soared overhead like they owned the place, porpoises popped up with casual greetings, and salmon leapt out of the water as if auditioning for Cirque du Soleil. Seals lounged on the rocks, clearly unimpressed by our paddling technique.
After crossing the channel, we aimed between Shaw and Crane Islands, then rounded past Deer Harbor on Orcas Island before finally reaching our home base for the next two nights: Jones Island Marine State Park. Since there’s no ferry service, you can only arrive by kayak or private boat, which makes it feel like you’ve stumbled onto your own private paradise.
The first campsite we pulled into was already packed with fellow adventurers, but luck was on our side. We paddled a little further to the west side of the island and scored wide-open, empty campsites—complete with front-row sunset views. Jackpot.
Tents pitched and lunch devoured, the afternoon unfolded into pure island bliss: basking in the sunshine, watercolor painting in the salt-kissed breeze, and collectively agreeing that life was pretty darn perfect. Even the threat of evening rain couldn’t dampen the mood.
As the day wrapped up, the sky delivered one of those sunsets you wish you could bottle up and take home—brilliant golds and pinks melting into the horizon. A few seals decided to stage a playful water show just offshore while we savored another fantastic dinner (with—you guessed it—more wine).
By bedtime, a few light sprinkles tapped on the tents like a lullaby, and I drifted off warm, cozy, and grateful. Tomorrow would be Day 3, but for now, Jones Island was absolute magic.
Day 3: Wildflowers, Seals, and Island Magic
Day 3 greeted us with a gift: no rain and the promise of sunshine. Spirits were high as we set out to explore Yellow Island and McConnel Island—two very different but equally magical stops.
Now, Yellow Island isn’t just any island. It’s a protected nature conservancy, and if your group is larger than six (like ours), you actually need special permission to visit. Why? Because it’s one of the San Juans’ rarest ecological treasures—a grassland ecosystem bursting with wildflowers and alive with birdsong. In peak season, it’s basically like stepping into a painter’s palette that spilled across the island.
When we landed, we were greeted by the island’s caretaker, who shared the island’s history and pointed out the rustic little cabin still used by The Nature Conservancy today. After the talk, we wandered along the trails, stopping often to marvel at wildflowers, watch birds flitting about, and laugh at the seals sprawled on the rocks like sunbathing divas.
From there, it was on to McConnel Island. We stuck to the public side, set up camp chairs, and enjoyed a leisurely lunch in the sunshine. The rest of the stop was pure relaxation: sketching and painting the coastal scenery, swapping stories, and soaking in that deep, contented silence you only get on tiny islands surrounded by big water.
Eventually, we paddled back to our base camp on Jones Island, where the adventure wasn’t quite over. Some of us laced up shoes and hiked a big loop around the island, rewarded with sweeping views and that delicious sense of being tucked away from the world. Evening brought another stellar dinner (our guides really outdid themselves), and as the stars crept out, we tucked into our tents, resting up for Day 4: the return paddle to San Juan Island.
Day 4: The Grand Finale (and the Whales Deliver!)
Day 4 dawned with a bittersweet vibe: it was pack-up-and-paddle-home day. After one last hearty camp breakfast (seriously, our guides deserved medals for their cooking), we got the lowdown on the day ahead. The good news? No rain. The bad news? We’d be paddling into both current and wind all the way back. Cue collective sigh.
The first challenge was crossing the San Juan Channel again, with clear instructions from our guides: “Keep paddling—don’t lose ground.” Easier said than done. There were moments it felt like we were paddling on a treadmill, but then a porpoise would surface nearby, a seal would pop its head up like a curious dog, or pink salmon would leap dramatically out of the water. These little distractions made us forget (at least for a few minutes) that progress was… slow.
Eventually, we landed at Point Caution, just outside San Juan Harbor, for one last well-earned lunch. Bellies full and arms rested, we pushed off for the final stretch. Spirits were high, but a tinge of disappointment lingered—we’d seen so much wildlife, yet the iconic whale sighting had eluded us. My kayak partner and I had already decided it was okay. The trip had been incredible, whale or no whale.
But the San Juans weren’t done surprising us.
About an hour after lunch, nearing Friday Harbor, our guides shouted: “The ferry just pulled in—if we want to cross before it heads back out, we need to go. Now.” Adrenaline surged. Nobody wanted to be “that group” holding up a ferry, so we dug in, paddles churning.
And then it happened. Out of the corner of my eye, I thought I saw a puff of spray. My heart skipped a beat. “Nah,” I told myself, “wishful thinking.” A minute later—another spray. This time unmistakable. Whales. Three of them.
We froze mid-channel, paddles resting across the boats, and erupted into cheers as the whales surfaced again, sleek and powerful, gliding past as if they were escorting us home. It was pure magic—one of those goosebump moments you know you’ll replay in your memory forever.
The last half-hour back to shore flew by on a wave of whale-fueled joy. By the time we carried the kayaks back to the vans, we were exhausted, exhilarated, and grinning ear to ear.
Mission accomplished: four days of laughter, paddling, painting,
wildlife galore… and, at last, whales.
Top 10 Must-Haves for a Successful Kayak Adventure
(a.k.a. How to Stay Warm, Dry & Happy Instead of Cold, Wet & Grumpy)
1. Follow the Gear List Like It’s Gospel
The packing list from Outdoor Odysseys Sea Kayaking is spot-on. Seriously—don’t wing it. They know what keeps people happy (and dry).
2. A Real Waterproof Jacket (Not Just “Cute Rainwear”)
I brought the NRS High Tide Jacket—cozy, warm, and armed with velcro cuffs that stopped salty seawater from sneaking up my sleeves. Armpit puddles = 0, Me = 1.
3. Kayaking Gloves = Finger-Saving Superheroes
Your hands are your engines. Gloves prevent blisters, keep you warm, and make paddling way more enjoyable. Forget them, and you’ll regret it.
4. Footwear That Loves Water (and Loves You Back)
Water shoes = good.
Booties = better.I wore bootie socks under water shoes—game changer.
Dry socks + camp shoes at the end of the day = instant joy.
5. Quick-Dry Shirt for Paddling
On the water, I only needed a short-sleeve quick-dry shirt under my jacket. Minimal layers while paddling = maximum comfort.
6. Camp Layers You’ll Actually Love
Once the sun dips, the temperature dips harder. Pack:
A fleece jacket (your cozy camp BFF).
One or two thin, warm long-sleeved shirts for layering.Sipping tea (or wine) around camp in fleece? Bliss.
7. A Trustworthy Tent, Sleeping Bag & Mat
This isn’t the time to gamble with gear. Storm-worthy is the only kind of tent you want. A soggy sleeping bag is the stuff of nightmares.
8. Snacks, Snacks, Snacks
Yes, the guides feed you well. But kayaking burns calories like crazy. That mid-afternoon granola bar or chocolate stash will feel like fine dining.
9. A Sense of Humor
Rain will fall. Currents will test you. Salmon will leap in your face. Embrace the chaos—it’s part of the fun.
10. A Camera (or Cell Phone) to Capture the Magic
From whales and eagles to glowing sunsets and goofy campfire selfies—you’ll want proof this trip wasn’t just a dream. If you’re relying on your phone, pack a solar charger. (Because nothing kills the vibe like 1% battery right before the whales show up.)
✅ The bottom line: The right gear keeps you warm and dry, the snacks keep you fueled, and the humor keeps you sane. Nail these 10, and you’ll spend less time shivering and more time laughing, paddling, and soaking in the adventure.
Ready to Plan Your Kayak Adventure?
Whether you’re dreaming of paddling alongside porpoises, watching the sun set from a quiet island campsite, or just trying not to tip over while laughing with friends—your adventure is waiting.
I’d love to help you plan it! From gear tips to route ideas (and maybe even which snacks pack best in a dry bag), I can help you get on the water feeling prepared, confident, and excited.
✨ Let’s make your kayak adventure one for the memory books.
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