Paddles, Pedal & Paint, Part 1: Planning the Ultimate Kayaking Trip to the San Juan Islands

Watercolor and Kayaking with Outdoor Odysseys: Your Ultimate Guide to Kayaking in the San Juan Islands

I slammed “BOOK NOW” like it was a Taylor Swift presale. That’s right, folks—Departure: August 13th! Cue the dramatic music and floatplane propellers. This blog post is your glitter-covered, all-access backstage pass to everything I’ve learned while prepping for this five-day, salt-kissed, pedal-island adventure, watercolor-splashed, kayak-powered adventure of a lifetime.

What’s the plan, you ask?

Think of it as summer camp for your inner mermaid-meets-biker-meets-“why do my arms hurt?” explorer. We’re kicking things off with a day of biking around Lopez Island (aka the charming, laid-back cousin of the San Juans), followed by four glorious days of kayaking and dabbling in watercolor painting.

And before you say “but I don’t paint…” guess what? Neither do I. The last thing I painted was a rock in third grade, and it still looked like a potato. No experience necessary—just bring your curiosity, sunscreen, and a sense of humor.

Who is this for?

• Already booked? You're my people. Start doing shoulder rolls.

• Thinking about it? Lean in closer, friend. This blog is your one-stop paddle shop for everything you need to know—from “where do I put my snacks?” to “how do I emotionally prepare for a floatplane?”

So grab your metaphorical (or literal) paddle, because this trip is equal parts splashy, soulful, and spectacularly awkward in the best way possible.

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Introducing: Outdoor Odysseys: Watercolor & Kayaking Trip

Overview: Paddle, Paint & Rewild Your Soul: A Creative Journey with Katherine Homes

Ready to swap your inbox for ocean spray and your to-do list for a paintbrush? Join environmental artist Katherine Homes and Outdoor Odysseys for an unforgettable four-day kayaking and watercolor adventure through the breathtaking San Juan Islands. This trip is your invitation to disconnect from the noise and reconnect with your wild, creative self.

We'll spend our days gliding through sparkling waters, encountering marine wildlife (think seals, porpoises, maybe even an octopus!), and setting up camp under starlit skies. Expect multi-course campfire cuisine, local wine, and the kind of shooting stars that make you forget about cell service entirely.

No painting experience? No problem. This journey is for beginner to intermediate painters with an adventurous spirit—you just need curiosity and a willingness to explore. Katherine’s work is rooted in environmental connection and honoring the wild—both out there and within ourselves. Together, we’ll slow down, breathe deep, and discover how art becomes a bridge between our inner landscapes and the natural world.

Each day includes a gentle mix of basic watercolor techniques—color mixing, sketching, and playful experimentation. Some days we’ll be inspired by seaweed tangled with shells, others by wind-twisted driftwood or a sweeping forest view. You can follow your own muse or join the group in choosing a subject—either way, you’ll come away with more than just a painting. You'll return with stories, salt in your hair, and a rekindled connection to nature.

🌊 What's Included:

• 🛶 Kayaking & Camping Gear

  • Sea kayaks, paddles, spray skirts, and dry bags

  • Life vests (PFDs)

  • Tents and sleeping pads (possibly sleeping bags too—confirm with the outfitter)

  👩‍🎨 Art Supplies

  • Watercolor materials (paints, paper, brushes)

  • Sketchbooks or journals

  • Instruction and support from Katherine Homes

  🍽 Meals & Beverages

  • All meals from lunch on Day 1 through lunch on Day 4

  • Gourmet multi-course dinners cooked outdoors

  • Local wine (often with dinner)

  🌿 Professional Support

  • Experienced sea kayaking guides

  • Art facilitation by Katherine Homes

  • Naturalist knowledge and wildlife spotting support

  🏕 Logistics & Safety

  • Group camping reservations

  • Transportation logistics for gear

  • Safety briefings and paddling instruction

  • Emergency support or evacuation plan

  🌅 Extras

  • Stargazing, beach walks, and quiet time for reflection or journaling

  • Optional short hikes or explorations around camp

  • A flexible pace—some solo painting time, some group sessions

  

  
  

The Itinerary: Ready, Set.... Pedal, paddle, paint!

Day 1: Pedal-Powered Paradise on Lopez Island

Let the island magic begin! I’m kicking things off on Lopez Island, the chill, bike-friendly gem of the San Juans. I’ve got a trusty two-wheeled sidekick reserved from Village Cycles, and get this—they’re delivering it right to the ferry dock. I step off the boat, and boom: my adventure-mobile is waiting like a loyal steed.

My digs for the night? A cozy glamping tent at Lopez Farm Cottages & Tent Camping—because I like my stargazing with a side of real pillows and fairy lights.

The day’s agenda is full of low-key wonder:

• 🌊 Shark Reef Sanctuary for rugged coastal views and wildlife peeping (seals, sea lions, maybe an eagle or two).

• 🏖 Spencer Spit State Park for beach vibes, tidepool wandering, and pretending I’m in a Pacific Northwest postcard.

• 🪶 Iceberg Point for a soul-filling hike and prime birdwatching—I’m talking clifftop trails, salty breezes, and views that make your phone camera cry.

It’s pedal-powered freedom at its finest, and I’m here for every wind-swept, sun-dappled minute of it.

Day 2: From LoCo to FriHo – Island Hopping in Style

This morning, I'm squeezing in a few final hours of Lopez Island magic—maybe one more coastline cruise or a last-minute snack stop (because ferry snacks don’t hit the same). Then it's back to the harbor to return my noble steed (aka rented bike) and hop aboard the ferry to San Juan Island.

Next stop: Friday Harbor, where I’ll be treating myself to a well-earned night of R&R at the dreamy Box Inn & Spa. Think plush beds, chill vibes, and possibly a hot tub situation. It's the perfect reset before the paddles hit the water and the kayak adventure begins.

One island down, four more days of salty adventure ahead!

Day 3: Launch & First Strokes

We kick things off in Friday Harbor, where your Outdoor Odysseys guides meet the group (6–12 paddlers total). After a scenic van ride to the launch site, you’ll pack up, get a paddling orientation, and hit the water once everyone feels confident. We'll kayak the stunning Haro Strait—keep your eyes peeled for whales! After a hearty shoreside lunch, we paddle to remote Reid Harbor on Stuart Island. Set up camp, unwind under the trees, and enjoy a three-course dinner with wine as the sun sets.

Day 4: Orcas, Paints & Bioluminescence

Today’s all about circling Stuart Island—prime orca territory. Expect sea cliffs, eagles, sea lions, and jaw-dropping views of Mount Baker. Back at camp, warm up post-plunge with hot chocolate or wine, then pick up your paintbrush for a late afternoon watercolor session. After dinner? Join a magical night paddle to witness glowing bioluminescence.

Day 5: Wild Islands & Sunset Art

After breakfast, we paddle to Speiden Island, scanning for exotic wildlife and bald eagles. Then we cross the channel to Jones Island—a kayaker’s paradise ringed with forest and waterfront campsites. Paint on the beach, feast on more campfire cuisine, and enjoy what might be the best sunset in the San Juans.

Day 6: Sunrise Sketches & Wasp Island Maze

We’ll greet our final morning with a serene sunrise sketch session, paintbrush in one hand, coffee in the other—channeling that golden light like true outdoor artists. After packing up camp, we’ll weave our way through the winding channels of the Wasp Islands, a paddler’s playground of rocky islets and hidden coves.

Our last lunch stop is on Turn Island, a perfect farewell picnic spot before we paddle the home stretch to San Juan’s east side. By 2–4 PM, we’ll be back in Friday Harbor—salty, sun-kissed, and maybe just a little reluctant to say goodbye.

But don’t worry—I’ll be swapping my tent for luxe digs tonight, checking back into the Box Inn & Spa for one last cozy island sleep (with real walls and indoor plumbing!).

Day 7: Homeward Bound (With Coffee in Hand)

Like all epic adventures, this one wraps with a sunrise sendoff. It’s an early start as I meet the Island Airporter shuttle at 5:05 AM, conveniently just a stone’s throw from my cozy bed at the Box Inn & Spa. (Bless them for that.)

This magical little shuttle zips travelers between Friday Harbor and SEA-TAC, making the island-to-airport journey refreshingly painless. By 9:30 AM, I’ll be checking in at the Seattle airport, coffee-fueled and kayak-core fulfilled, ready to catch my 11:30 AM flight back to Bend, Oregon.

My bags are heavier (with sea-salted gear and probably a few shells), but my heart? Totally full.

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Getting There: Logistics (aka How to Avoid a Panic at Sea Level)

So you’re in. Or you’re maybe in. Either way, you’ve gotta get yourself to Friday Harbor on San Juan Island, where the real adventure begins. Here’s your logistics lowdown:

Note: All my options start from Seattle-Tacoma International Airport (SEA) because that’s the rabbit hole I personally tumbled down. Honestly? I wasn’t about to cross-reference flight paths from every North American airport just for fun. BUT—if you’re flying into somewhere else like Vancouver International in Canada and need a route plan? I’m your gal. I will happily geek out on ferry schedules for the adventure bound.

🚗 + 🛳 Car Rental + Ferry from Anacortes

Best for: Control enthusiasts, road trip romantics, podcast bingers, and anyone who prefers to choose when they land in water.

Rent a car at SEA-TAC, cue up your favorite playlist, and enjoy a scenic 2.5-hour drive north to the Anacortes Ferry Terminal. You'll probably want to park in long-term parking (~$40 for 5 days), then strut onto the ferry like your in an REI ad—snacks in hand, bags under my own supervision, no baggage claim drama in sight.

You’ll sail into Friday Harbor 90 minutes later, calm, collected, and snack-happy.

Why would I choose this? Because I like calling the shots. This route is perfect if you want full control over your timing, your snacks, your playlist, and your luggage. It’s relaxed, flexible, and you get to avoid coordinating with shuttles and strangers. Honestly? I’d probably have picked this if I were starting or ending my trip on a weekend—BECAUSE the weekend shuttle from SEA to Anacortes requires a transfer (a.k.a. “extra logistics I didn’t vibe with”). If you’re coming midweek or enjoy a good road trip, this one’s a winner.

Pro Tips:

• Don’t forget to bring your overnight bag (the car’s not coming with you).

• The ferry ride is supposed to be a stunner: seals, eagles, mountains, and possibly dolphins.

• Walk-on ferry passengers don’t need a reservation—score! (though, I did purchase my ticket online so it's one less thing to do the day of!)

My Route (and Favorite This Time):

🚌 Option 2: Shuttle + Ferry

Best for: Car-free folks and nap-in-transit enthusiasts.

If traveling on a Weekend:

Bellair Airporter Shuttle runs between Seattle-Tacoma International Airport (SEA) and the Anacortes ferry terminal, making it a great option for car-free travelers. Just a heads-up—it’s not a direct route. The shuttle makes a few stops along the I-5 corridor (think Mount Vernon, Burlington, etc.), so expect a slightly longer ride.

If you are Traveling Monday-Friday (like me!)

Island Airporter offers a smooth, no-drama shuttle from SEA-TAC Airport straight to the San Juan Islands, Monday through Friday. No confusing transfers, no unnecessary stops—just you, your luggage, and a direct ride to island time. Just be sure to book ahead, and look for pickup at the south end of baggage claim, right outside Door 00 or Door 2. Easy-peasy.

Lucky me—I’m traveling to and from the islands on a weekday (cue the dance music), so this dreamy, hassle-free option was totally in the cards. I’ll get scooped up at SEA-TAC, enjoy a scenic drive to the ferry terminal, hop aboard the boat, and roll right onto Lopez Island without lifting a finger. Island mode: activated.

🛩 Option 3: Fly with Kenmore Air (*or one of the other options*)

AKA: “Let’s launch ourselves into the clouds and hope we stick the landing—in water.”

Best for: People with strong stomachs and excellent travel insurance.

Kenmore Air offers flights from Boeing Field (wheeled) and Lake Union (floatplanes) directly to Friday Harbor. It’s fast (45 minutes), it’s scenic, and it’s thrilling. 👉 kenmoreair.com. They’ll even shuttle you from SEA to the terminal. Bless.

🚂 Option 4: Train + Ferry

Best for: Novel readers, nature lovers, and vintage travel romantics.

Take Amtrak Cascades from Seattle to Mount Vernon, then Uber to Anacortes, and ferry it from there. You’ll feel like the main character in a charming indie film.

🛥️ Option 5: Private Charter

Best for: Bachelorettes, boat captains, and those living out their “rich aunt energy.”

If you’ve got the budget and the vibes, charter a private boat, helicopter, or seaplane. Arrive like the mermaid queen you are.

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🧡 Pro Tips for Peak Joy

• Book early! These trips fill faster than a Taylor Swift stadium.

• Pack light but smart. Outdoor Odysseys has your packing list dialed in—just follow it.

• Be open. To friendships, new experiences, and maybe singing sea shanties (and in my case... a bit of painting).

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🚣‍♀️ This Isn’t Just Kayaking—It’s Soul-Level Self-Care

With Outdoor Odysseys Kayaking (and Paint), you’re not just paddling—you’re pressing pause on the chaos. It’s part wilderness therapy, part creative retreat, and a full-on reminder that you’re powerful, free, and yes—nature-approved bathroom breaks are 100% legit.

Not vibing with painting? No worries. Their trip lineup is basically a choose-your-own-adventure for the soul—ranging from single-day paddles to multi-day escapes that leave you salt-kissed and glowing.

• 🧘‍♀️ Yoga more your thing? The 3-Day Yoga & Kayaking Tour is basically a floating retreat.

• 🧘‍♂️ Craving quiet? Their Meditation & Kayaking Tour is your new favorite still point in a spinning world.

If you love water, wonder, and a little woo, they’ve got something magical with your name on it. Check out their full tour lineup here (and no, I’m not getting paid—I’m just a fan with paddle-blistered hands and a happy heart).

Coming on the trip? Amazing! I’ll see you at the ferry with granola bars and a dry bag full of excitement. Just here for the vicarious thrill? Totally cool. Come back for Part 2 beginning August 13th—there will be stories, possibly sunburns, and definitely snacks. Want to join in real life? LET’S GOOOO. I’ve got the sunscreen—you bring the trail mix.