Flying private’s a lot less glamorous than people think sometimes. Sure, you get cool perks and see insane places, but a lot of it is just being on call, waiting for the phone to buzz, making sure you’re 100% ready to go at a moment’s notice. That’s exactly what happened when I flew my client into Aspen last month for a weeklong stay.
We touched down at Aspen/Pitkin County Airport on a bluebird afternoon, the mountains still holding onto a little snow, the tarmac shimmering from the sun. Flight was easy—clear skies, light headwind. The client’s car was already waiting, blacked out SUV with all the bells and whistles. After we shut down the Citation and buttoned her up, I made sure the luggage was squared away and then basically got told, “Thanks, see you in a week.”
Which is exactly how I like it.
Once the client was off living the dream—probably at some $10k-a-night chalet in Red Mountain—I had the better part of seven days to myself. Had to stay local, had to stay ready, but otherwise, my time was mine. And if you’re gonna be “stuck” somewhere, you could do a hell of a lot worse than Aspen.
First thing I did was get myself into town. I’d arranged for an Aspen private car service ahead of time because screw messing around with rental counters and parking drama. Plus, when you’re rolling a flight suit and dragging a headset bag around, you already look half-homeless. A clean, quiet ride downtown made a big difference.
I posted up at a small lodge just off Main Street—nothing fancy, but walking distance to just about everything. And yeah, prices were crazy compared to back home, but whatever. Client was footing the bill for accommodations (part of the deal), and I wasn’t about to waste it.
First couple days I just explored. Walked all around town, grabbed coffee at a place called Local, cruised through a few galleries I had no business being in. You ever pretend like you’re gonna buy a $30k painting? I did, and let me tell you, it’s hilarious when you’re wearing sneakers and a trucker hat.
Hiked up Smuggler Mountain on Tuesday—trail was a little mucky from snowmelt but manageable. It’s a good climb, nothing technical, and at the top you get a panoramic view of Aspen that seriously looks fake. Snapped about a hundred photos and managed to only slip once coming down, which felt like a personal victory.
Midweek I rented a bike (e-bike, don’t judge me) and hit the Rio Grande Trail. Probably did 20 miles round trip without even realizing it. That path winds along the river and you can basically cruise for hours if you want. Found a little burger stand halfway through, grabbed a cheeseburger the size of my head, and sat by the river pretending I wasn’t thinking about flight schedules.
Had to stay within cell service most of the time, so I didn’t get too deep into the backcountry. It was weird—being in a place that screams “adventure” and knowing you can’t go full-send because you might get called back to the airport with an hour’s notice. But honestly? The chill vibe kinda suited me.
Ate way too good while I was there. One night I hit White House Tavern and absolutely destroyed their fried chicken sandwich. Another night I went fancier, sat at the bar at Steakhouse No. 316, ordered a steak, and just people-watched. Aspen’s a wild mix—you’ll see a guy in ski boots next to a lady wearing a fur coat and carrying a dog that probably flew private too.
Met a few other pilots hanging around town, which happens more than you’d think. There’s kind of a secret brotherhood of us lingering near airports like we’re in some exclusive club nobody talks about. Grabbed beers with a guy flying a Gulfstream and another guy doing short hops for some billionaire’s ski crew. Swapped horror stories and plane pics until closing time.
Toward the end of the trip, the client’s assistant called me and gave me the heads up they were planning to head out early. No biggie—part of the job. Booked the prep services for the plane, made sure we were fueled up, filed the flight plan.
And since they wanted a last-minute ride to Denver instead of flying commercial out of ASE (don’t ask me why rich people make weird choices sometimes), I ended up arranging an Aspen to Denver limo service for them. They wanted something comfortable but low-key, no logos, no fuss. Found a service that fit the bill, made it happen, and just like that, they were gone.
I had one last free afternoon before my own flight home, so I splurged on a ticket to the Aspen Art Museum. Honestly, I didn’t expect much, but it kinda blew me away. Some of the installations there are unreal, and the rooftop café had a view that made me want to miss my own plane. (Don’t worry, I didn’t.)
Wrapped up the week with one more lap around town, grabbed some pastries to-go, and sat on a bench just soaking up the sun. It’s rare in this gig to get real downtime without pressure, and Aspen treated me way better than I probably deserved.
Flew back out the next morning just after sunrise, smooth as glass all the way back to home base. Spent half the flight daydreaming about those mountain trails and wondering when I could swing back through—not for work, not on call, but just for me.