Aspen wasn’t exactly on my radar this year. I’d had a busy spring, some client work in California and then a last-minute destination shoot in Mexico that went completely sideways. By the time October rolled around, I was pretty much planning to just shut off and recharge for the season. But then I got a call from one of my favorite clients — a lifestyle brand I’ve worked with a few times — asking if I’d be available for a fall-to-winter transition shoot in the Rockies.
The brief was simple: golden leaves turning to snow, cozy textures, early firepit vibes. They wanted that blend of luxury and grounded nature that only places like Aspen can pull off. I hesitated, mostly because I was tired and not super stoked on the logistics, but they sweetened the deal by offering to cover everything — flight, lodge, local transport. “Just bring the gear and the eye,” they said. And I mean, that’s hard to turn down.
I flew into Denver because the connections to Aspen were either too expensive or too sketchy. It’s always a gamble flying into those small mountain airports. The issue, of course, was how to get from Denver to Aspen without spending four hours behind the wheel of a rental in unpredictable weather with $15K worth of gear in the back. I’ve done that before. Never again.
So I hit up the client to ask what the plan was for transport. They sent over details, and I saw they’d booked me with a local chauffeur company — not a national chain, not a shuttle, just a small operation with a reputation for getting creatives and execs up the mountain without the stress. I didn’t think much of it at the time. Transportation usually falls under “nice if it’s good, but doesn’t matter as long as it’s not bad.”
Turns out it mattered a lot.
My driver texted me before I even landed to confirm where he’d be, what the vehicle would look like, and how long we’d wait if I got delayed. He met me at baggage claim, helped with the gear, didn’t ask any weird questions about it. The car was immaculate — black SUV, clearly prepped for mountain driving, warm as soon as I got in. No small talk unless I initiated it. I’ve worked with dozens of transport people in this job, and the ones who just read the vibe and adapt? Rare. This guy had it dialed in.
We hit the road and I zoned out for most of it. Answered emails, scrolled through location folders, tried to figure out if the late season snow was going to mess up our shot list. Every time I glanced up, we were further from the city and deeper into those winding stretches of highway that get really sketchy when the temperature drops. I didn’t worry. He drove like someone who’d done it a thousand times and didn’t need to prove it.
About halfway up, he offered a stop if I needed to grab food or a bathroom. I didn’t, but I appreciated that it wasn’t just a point A to B drop — he was clearly used to the fact that not everyone in his car was a seasoned mountain traveler. We rolled into Aspen just before dusk, snow starting to fall in that gentle way it does before it gets serious. He pulled straight into the private lodge, unloaded everything, gave me his card in case anything changed, and left without a fuss.
I don’t know why that level of calm competence surprised me, but it did. I’ve worked jobs where just getting there is a logistical nightmare. Drivers get lost. People show up late. Gear gets shoved into trunks like it’s luggage. But this? This was as smooth as if I’d been driving myself — maybe smoother, actually, since I wasn’t stressed the whole time. If anyone in my line of work asked me about getting around Aspen, I’d immediately recommend this Aspen private chauffeur. No fluff, no oversell — just a solid experience that let me do my job without extra noise.
The rest of the shoot went well. Better than well, honestly. We caught the exact transition the brand wanted — gold leaves hanging on under a layer of frost, fog rolling off the river early in the morning, that quiet stillness that makes Aspen feel like another planet when it’s off-season. I had more freedom than usual with the creative, so I shot a lot of film, did some handheld video, even experimented with some slow shutter stuff I’d been meaning to try for a while.
There were a couple days where I needed to scout spots outside of town, and each time I just sent a quick text and the car was there — no delays, no confusion about addresses, and always someone who already knew how to get where I was going without needing to GPS it mid-drive. I didn’t think twice about leaving gear in the car while I walked locations. That trust isn’t common, and I don’t throw it around lightly.
I wrapped the shoot on a Thursday, and we had a little sendoff dinner at a tiny place tucked into the edge of town. The kind of spot that’s impossible to get into on weekends but half-empty on a cold weekday night. On the way back to the lodge, my driver asked how the shoot went — not like a generic “How was your day?” but like he actually wanted to know if things worked out. I told him yeah, it had. Better than I expected.
The next morning, he was there at 6 a.m. sharp, car warmed up, coffee waiting in the cupholder. We drove back in silence mostly, just watching the mountains wake up. I edited a few selects from my laptop in the backseat, uploaded them using the car’s hotspot (yes, really), and got a head start on client delivery before we even hit the highway.
It’s easy to overlook the impact of transport on a work trip like that. But the older I get, the more I realize that the things that seem small — the ride to and from — often shape the entire experience. If that had gone wrong, I would’ve started the job stressed and ended it drained. But because it didn’t, I showed up calm, focused, and able to do what I was there to do.
I’ve since passed their name to two other photographers and a producer I trust. And when the brand said they wanted to book another shoot in spring, I told them: use the same team. Don’t change what works.
If anyone ever asks me who’s the best car service in Aspen, I’ve got my answer. It’s not the flashiest one. Not the one with the biggest ad budget. It’s the one that made my job easier without asking for attention. That, to me, is luxury.
