Goodbye van life (for now), hello Airstream life!

My first experience towing our Airstream was down a serpentine 1.5 mile driveway, a steep descent through an overgrown orchard. At the exit gate, I somehow forgot I was lugging a 28’ tail behind me and almost hauled the trailer over a tall curb and through a giant bush. *gulp*

Chelsea immediately adopted a mantra: trailer trailer trailer, which she chanted anytime I was turning. Not to be dissuaded, my first gas station stop left the trailer hanging so far out that I partially blocked the entrance. I earned a few stink eyes from other drivers as they crept over a curb to get past me.

At least I was able to back the trailer into place in the pitch dark when we got home! Hey, one outta three ain’t bad…

Soooo yup, this whole Airstream thing is a giant disaster going to be a learning experience.

Chelsea riding in the back of the truck down the initial driveway orchard gauntlet.

Why an Airstream?

Like many people, we’ve experienced a rough few years. COVID headaches, some health drama for me and Chelsea, a business cycle that took down my company… It feels like a lot, at least relative to halcyon days of yore. We can’t shake the feeling that life is short and fragile and that we’ve gotta go live some of our dreams.

In short, after 6+ years in Bend, we feel VERY in need of some wandering (traipsing, if you will?). Time to seek space to clear our heads and get recentered.

While our senior kitty Oliver is still with us and my Italian citizenship still isn’t official (someday), we aren’t psyched on international travel. We considered renting Airbnbs around the U.S., but wow, expensive much? Also, we want our own space vs. transitioning to new lodging constantly. However, the idea of long-term van travel doesn’t feel appealing.

So after kicking it around for awhile, we bought a used 2017 Flying Cloud Airstream. If I say so myself, she’s a beaut! Cozy, light and bright inside, with all the amenities to make long-term travel comfy and sustainable.

I hope my head isn’t really this tall…

Our goals with the Airstream:

  • A comfortable escape pod for smoke season. Sadly, it’s the 5th season here in Bend—we’re currently mired in an apocalyptic haze as I write this. Also, we’re over winter and want to hit the road for that.
  • A way to stop in a place and stay longer, a week or two instead of night. I’m planning to outfit the Airstream for extended boondocking.
  • Not having to constantly pack stuff up anytime we need to head to the grocery store or go for a hike. Aka parking the trailer and having a separate 4×4 run-around vehicle that can go anywhere. (As a friend said, “I think I speak for all of your followers when I say I want to hear more about THAT TRUCK.”)
Searching for the perfect truck…
  • A desire for more space! The van has ~15 sf of floor area. It’s a small-but-effective space and I love traveling in it, but not for long periods of time. The trailer is under 200sf, another world in terms of space.
  • More comfortable seating. In the van, we always feel perched, not kicked back and comfy. For extended travel, we’ve realized we want a real lounge space.
  • I want to play lots of piano, my fav hobby these days (apologies to my mountain bike). Yup, I’m still fired up on learning the music of old dead white guys from centuries ago. Hey, it lights me up…I’m going with it! There’s a perfect space to set up a piano between the twin beds up front in the Airstream.
Holy square footage, batman!

In short, we aren’t the spunky early-30 somethings who set off in our van without any running water or lights. A decade later, we want something closer to a tiny house. Yup, getting soft. I’ll own that!

Also, van life has a kind of momentum to it where we are constantly on the go, driving to and fro seeking excitement. Two nights at Bryce Canyon, then charging off to Zion National Park for a night, then onward to Gooseberry Mesa… and so on. It’s GREAT for short trips, but akin to flitting about Europe and seeing a 17 cities and 12 countries in a whirlwind trip. Our goal with the Airstream is to set up the conditions to thrive with slower travel.

Modifying the A/C (whoa, we have A/C!) with an EasyStart.

What am I excited about? So much.

Waking up in nature. NOVELTY. Backing the trailer up to the ocean, a river, or the North Rim of the Grand Canyon and eating breakfast with that view. Exploring whatever area we’re in. Playing piano outside under big trees. Drawing anything and everything. Reading a ton. LESS HOUSE MAINTENANCE. Finally learning how to surf and returning to a consistent yoga practice. Parking near famous trails and experiencing them more than once. Camping with friends along the way.

For our first long trip, I’m planning to just relax, to see what it feels like to not check work email or worry about payroll or need a cell signal all the time. It’s been 17 years since I had that kind of space.

Honestly, this just feel like a big life curveball out of the blue. Trailer life?! Never, ever would I have seen this coming. It’s an experiment in a different style of living, mobility with more comfort. Many people love it, but is it for us? We’ll see!

I suspect it’ll be fantastic. At least once I learn how to pull a trailer without leaving a swath of destruction behind me.

Oh, did someone else want to get into this gas station? (Rental truck, btw.)


  • Yes, this feels like a massive change from how we’ve traveled in the past. I’ll be in therapy for at least a year to grapple with the loss of my VanMan street cred.
  • No, this isn’t a mid-life crisis and no, I don’t plan on getting a paunch. (Har har, George.)
  • Yes, we bought a truck! And YES, I admit I’m excited to drive it. You can take the boy out of Idaho, but… After a ridiculous series of encounters with car salesman that reinforced everything negative I’ve ever heard, we found a rare used Ford F150 (in Idaho) with a heavy duty payload package that is going to kick ass and not feel like a monster truck. Well, kind of not a monster truck…
My dad picking up our for-sure-a-monster-truck in Idaho, where all such trucks live.
  • Yes, this will affect how we approach travel. We’re actually going to have to plan! No more turning up any fire road to search for a camping spot. A little upfront planning or scanning Google terrain should yield more epic boondocking spots perfect for longer stays. And yes, more campgrounds.
  • Yes, we still have plans for Italy and oh-so-much international travel. But my citizenship quest is still ongoing and all that’s down the road a bit. Europe will still be there, I suspect. (Go away, Putin.)
  • No, we are not selling our house. We love it, our neighborhood, and our neighbors. We’ll be back! However, we are planning to rent it. Interested in a fall/winter stay in a sweet modern house in Bend, Oregon with the feel of a botanical garden? Hit reply and send me an email!
  • Yes, our 19 YO super-senior cat Oliver is coming with us. In fact, he’s already started meowing at the front door to our house because he loves to visit the Airstream. It’s super cute how he sits by the trailer screen door and sniffs the breeze.
Oliver the security detail.
  • Nope, we are not selling the van. At least not yet… First I need to test out what long-term travel in a trailer is like. I’ve put too much work into the van to flippantly sell it. But I have envisioned what a pop-top camper on the truck would be like for shorter local trips, coupled with the Airstream for long jaunts. Ch-ch-ch-chaaanges!
  • The trailer is a 2017 Flying Cloud Airstream, the 27’ FBT (front bed twin). It’s in fabulous shape because the previous owner never used it and the one before that was afraid of towing. Gosh, why?
  • No, we have no idea how trailer stuff works. How does one use a stinky slinky? There will definitely be a learning curve! But I know van systems well from building and remodeling our van, not to mention DIYing solar on our house, so I’m optimistic it’ll work out. What could go wrong?

That’s a wrap. Much more to come on this latest jaunt, but right now I’ve gotta finish staining the front door trim. Getting our house ship-shape before launch!



Ready to awkwardly back up anywhere, anytime.