july 2026
Travsessed is
heading To San Juan Islands–Washington!
Outdoorsy Magic — A Hiking & Camping Weekend Adventure
This is the ultimate outdoorsy, fun long-weekend getaway—the kind of trip that fills your soul and smells like campfire and sea breeze.
Travsessed is heading to the San Juan Islands, one of Washington’s most breathtaking and untouched corners of the Pacific Northwest. This trip is all about coastal beauty, wild adventure, and that rugged-meets-relaxing vibe the PNW does best.
Think sunset whale watching, beautiful hikes, kayaking in one of the most stunning parts of the country, picnic lunches, stargazing and storytelling around the campfire, local wine, and delicious Pacific Northwest food that somehow tastes even better outdoors.
Where We’re Headed
San Juan Islands – A dreamy archipelago of over 170 islands scattered between Washington and Canada. Expect misty mornings, salty air, and postcard-worthy sunsets at every turn.
Friday Harbor – The charming harbor town where island time truly begins. Cafés, art galleries, local wine bars, and the perfect spot to watch the ferries drift in and out.
Orcas Island – The “gem of the San Juans,” known for its mountain peaks, lush forests, and panoramic views from Mount Constitution. The hiking here is unreal.
San Juan Island – Rugged coastlines, hidden coves, and some of the best whale-watching in the world. Keep an eye out for orcas gliding by at sunset.
Let Us Take Care of You!
Get yourself to Washington — we’ll handle the rest!
We’ve done all the researching, planning, organizing, and heavy lifting so you don’t have to.
This is the ultimate Pacific Northwest weekend getaway — all you have to do is show up with an open mind, a positive attitude, and be ready to relax, explore, and have fun with your new travel crew!
TRIP HIGHLIGHTS:
Sea kayak through the iconic San Juan Islands, one of the most breathtaking coastal regions in the Pacific Northwest
Private sunset whale-watching tour — experience golden-hour magic on the water, surrounded by orcas, sea lions, and bald eagles as the sun sets over the San Juan Islands
Summit Mount Constitution on Orcas Island for panoramic views of the sparkling coastline and snow-capped peaks
Uncover off-the-beaten-path adventures — hidden forest trails, mountain lakes, and secret coastal overlooks
Savor chef-prepared, locally sourced meals (with perfectly paired wines)
Sip and savor at a local winery, complete with a fun picnic lunch
Enjoy a weekend packed with adventure, connection, and unforgettable memories
The Ultimate Outdoorsy, Adventurous Weekend Experience!!
Trip Details:
4 Day Weekend Getaway
Dates:
July 24-July 27th, 2026
Cost:
$3,905.50
($250 coupon code can be applied for discount at check out)
What’s Included:
We’ve thought of everything — so you can just show up, unplug, and enjoy the adventure.
- All accommodations — cozy yurts and a peaceful night of glamping under the stars
- Expert local guides + full support team ensuring every detail runs seamlessly
- Two Travsessed hosts (Kim & Erran) guiding, coordinating, and bringing the good vibes all weekend long
- All meals included — delicious, freshly prepared breakfasts, picnic lunches, and dinners cooked by your guides (with local ingredients and wine pairings)
- Private sunset whale-watching tour — experience golden-hour magic on the water while spotting orcas, sea lions, and bald eagles from your private boat
- Guided sea kayaking adventure — paddle through pristine island waters with all equipment and safety instruction provided
- Wine tasting & vineyard picnic lunch at a charming local winery
- Hike Mount Constitution — complete with a packed trail lunch and breathtaking summit views
- All gratuities included — we tip hundreds of dollars on your behalf so you can just relax and enjoy the experience
- Transportation during the trip — including guest pickup, activity transfers, and island travel
- Off-the-beaten-path exploration time to wander the charming harbor towns, relax lakeside, or soak up the island vibe
What’s Not Included:
- Airfare to and from Washington
- Transportation to and from the San Juan Islands
- Travel insurance
- Meals not listed in the itinerary
- Optional or additional activities outside the planned itinerary
All Travsessed Adventures are very group oriented and we do the majority of activities together. Our goal is to create an experience where we can all connect, get to know each other, and share in the adventure together.
Trip Itinerary:
Subject to change…but this is the overall vibe.
We will provide a full trip itinerary, packing list, restaurant guide & more detailed trip info, once you have signed up.
Day 1
Welcome to the San Juan Islands!
Your Pacific Northwest weekend adventure kicks off as we meet at Memorial Circle around 10:30 a.m. to start the journey together.
We’ll kick off the adventure with a fun welcome picnic brunch, where you’ll get to know your Travsessed team and new travel friends.
After brunch, we’ll ease into island life with a 3.5-mile guided hike through American Camp and the Cattle Point Lighthouse — a stunning coastal trail filled with wildflowers, rugged cliffs, and sweeping ocean views that instantly set the tone for the weekend ahead.
Next, we’ll check into our cozy lakeside retreat, where we’ll be staying in beautiful, remote yurts — the perfect home base for the next two days of island exploration.
And yes, each yurt comes with its own private hot tub for the ultimate post-adventure unwind.
As the sun begins to set, we’ll head out on a private sunset whale-watching tour — an unforgettable evening spent cruising through waters home to orcas, sea lions, otters, and bald eagles. We’ll top off the night with a sunset dinner aboard our private boat — great food, wine, and incredible views. Sunset, wine, and orcas… what a way to kick off a magical weekend together!
MEALS INCLUDED: Brunch, Dinner with wine
Day 2
Paddle, Sip, and Savor the Islands
Wake up surrounded by nature and enjoy a fresh, guide-prepared breakfast — coffee in hand, lake views all around.
Then it’s time to hit the water for a guided sea kayaking tour from Roche Harbor. Paddle through calm island coves and keep your eyes peeled for seals, eagles, and maybe even an orca fin in the distance. Your guides will provide full instruction and gear, so all you have to do is show up ready to explore.
After working up an appetite, we’ll unwind with a wine tasting and picnic lunch at a local vineyard. Sip Washington wines, soak in the laid-back island atmosphere, and enjoy a chef-style spread prepared by your Travsessed team.
The afternoon is yours to relax, stroll the lakeside trails, or simply kick back with your new travel crew.
As the sun sets, we’ll gather for another guide-prepared dinner at camp.
MEALS INCLUDED: Breakfast, Picnic lunch, wine tasting, dinner
Day 3
Mountain Views & Glamping Under the Stars
After breakfast, we’ll head to Orcas Island for another unforgettable day of exploration. Lace up your boots for a scenic hike up Mount Constitution, where panoramic views of the San Juan Islands, sparkling bays, and distant snow-capped peaks make every step worth it.
We’ll enjoy a packed trail lunch before heading to Moran State Park, where we’ll set up camp among the towering evergreens and spend the night glamping on Orcas Island.
That evening, we’ll gather under the stars for a farewell dinner featuring a delicious local menu with wine pairings — the perfect finale to an incredible weekend of exploration, connection, and pure Pacific Northwest magic.
Relax around the fire, soak in the stillness of the park, and savor your island sunset with your new Travsessed family.
MEALS INCLUDED: Breakfast, Lunch, Dinner with wine Pairing
HIKE DETAILS: The summit trek up Mount Constitution is approximately 6.7 miles round-trip with about 1,500 ft of elevation gain
Day 4
Slow Morning & Island Goodbyes
Wake up to the sound of birds and the soft glow of the morning sun filtering through the trees. Enjoy one last group breakfast prepared by our incredible guides, savoring the slow start with a hot cup of coffee and island views.
Take your time this morning — sip your coffee by the water, wander the nearby trails, or simply relax and soak up the peaceful island magic. This is your moment to breathe, reflect, and do whatever feels good for your soul.
After breakfast, we’ll pack up camp and head to the charming town of Eastsound to browse local shops, have lunch and enjoy the island vibe before catching the ferry back to San Juan Island.
Once we arrive back in Friday Harbor, we’ll say our goodbyes (for now!) — hearts full, cameras full, and memories made to last a lifetime.
MEALS INCLUDED: Breakfast, Lunch
Travel and Arrival information
Once you’re signed up, we’ve got you covered! We’ll help you sort out all the logistics — how to get to and from Friday Harbor and what travel options work best for you.
Closest Airport: Seattle–Tacoma International Airport (SEA)
Your adventure begins and ends on San Juan Island, with our group meeting in Friday Harbor around 10:30 a.m. on Day 1.
To reach the island, you’ll first travel from Seattle to Anacortes, where all ferries to San Juan Island depart. From there, enjoy a 1.5-hour scenic ferry ride through the San Juan archipelago to Friday Harbor — the official start of your Travsessed adventure
arrival Details:
Airport: Seattle, WA (SEA)
Pick-Up Location: Friday Harbor, San Juan Island
Meeting Time: Around 10:30 a.m. on Day 1
Departure Details:
Drop-Off Location: Friday Harbor, San Juan Island
Return Time: TBD
Airport: Seattle, WA (SEA)
getting to friday harbor
Option 1 – Fly:
Take a quick charter flight from Seattle to Friday Harbor for the fastest route
Option 2 – Drive or Shuttle + Ferry:
Drive (≈ 2.5 hours) or take a shuttle (≈ 3.5 hours) from Seattle to Anacortes, then board the 1.5-hour ferry to Friday Harbor.
All ferries to San Juan Island depart from the Anacortes Ferry Terminal.
Our rendezvous point is within walking distance of both the ferry terminal and the island airport.
pro tip
We highly recommend arriving a day early in Seattle, Anacortes, or Friday Harbor to avoid potential travel delays from flights, ferries, or luggage mishaps — and to start your island weekend stress-free.
Activity Level: Active & Adventurous
This trip is designed for travelers who love to move, explore, and embrace adventure! We’ll be hiking, walking, and kayaking our way through some of the most beautiful parts of the San Juan Islands — so come ready to move your body and soak it all in.
No advanced experience is required — this is a great trip for beginners with an open/positive mindset.
You can expect:
Bring an open mind, a sense of adventure, and a good attitude — and you’ll be more than ready to conquer this unforgettable Pacific Northwest experience!
Why Travel With Travsessed
We’re Kim & Erran, a healthcare traveling couple & the founders of Travsessed.
We are travelers who are obsessed with travel!! We love traveling and researching & planning and we put our heart, souls and so much love and thought into every single detail and trip that we plan!!
We create one of a kind, small group, boutique travel experiences for healthcare workers (and their friends or partners)
We plan & organize all the things…so all you have to do is show up & have a good freakin time!!
We work closely with small local businesses, friends, and local guides to create a unique, one of a kind experience that you will not find anywhere else!!
We always get off the beaten path & dive into the local culture, food, people & experiences!
We go beyond the surface & way past the “highlights” to create experiences that will give you a deeper perspective, understanding & appreciation for the places you visit.
And we have a lot of fun along the way!!!
What Other Travelers Are Saying:
My trip to Peru with Kim & Erran was packed full of the perfect amount of everything my soul needed from, adventure to relaxation to communing with some of the coolest people I’ve ever met. Truly had the time of my life and look forward to embarking on another Travsessed adventure soon! Keep on doing what your doing. Travel changes a person to their core for the better and I really believe you two are fulfilling your life’s purpose.
Just got back from the most amazing trip to Machu Picchu in Peru with Travessesd!! It was truly an adventure trip of a lifetime! I can’t say enough good things about Kim and Erran and the whole Travessed experience- from start to finish it was perfectly planned and executed with a focus on excellent, beautiful, epic adventures where we were immersed in the local culture of Peru
Travsessed Peru was the most well-thought-out, adventurous, incredible trip! Kim and Erran do such an amazing job at creating a culturally immersive and unique journey! The group was an instant family that motivated and inspired each other the whole way! I couldn’t have planned a better trip to Peru, and I wouldn’t trade the memories, tears, laughter and love for anything!
Kim and Erran put on the best trip imaginable!! Not only did I get to experience a new country for the first time but I got to meet some of the most amazing people to do it with ♥️ I love that we didn’t just do “touristy” things but got to experience a lot of the culture. I would do it again in a heartbeat. 100/100
