Life as a Winter Photographer Isn’t as Glamorous as It Looks
If you’ve ever worked as a freelance photographer in the Rockies during winter, you know what it’s like to run entirely on caffeine, cold fingers, and the constant anxiety of being late. Between weddings, private events, corporate shoots, and last-minute commercial jobs, I’ve probably driven more miles between Aspen, Snowmass, and Vail in rental cars than I care to admit — usually on very little sleep, usually on slick roads, and usually regretting not hiring someone else to deal with it.
But I’ll be honest — I used to think that booking private transport in Aspen was only for the ultra-rich. You know, celebrities and CEOs getting whisked away to their chalets in Escalades with blackout windows. I figured it just wasn’t in the cards for someone like me who’s hauling camera gear, tripods, lighting kits, and half a dozen backup batteries that lose charge faster in the cold. Still, after one too many breakdowns (literal and emotional), I finally caved last season and started asking around for recs. I needed a better system.
The Recommendation That Finally Changed How I Work
That’s when one of the planners I work with regularly — someone who runs ultra high-end weddings out here — told me straight up, “Stop driving yourself. Just use Aspen Way To Go.” She said it like I should’ve already known, like it was common knowledge. But somehow, I’d never heard of them. Maybe because they’re not loud about their marketing. Maybe because they actually don’t need to be.
So I looked into it. Didn’t take long — the website was clean, easy to book through, and actually showed availability without me having to submit some weird inquiry form and wait two days. I locked in a full-day schedule that included three separate stops across Aspen and Snowmass — two weddings and one proposal shoot — and added a note about my equipment load just in case.
A Ride That Made My Job Easier From the First Minute
I didn’t expect much, honestly. I figured the driver would be on time (hopefully) and at least help me lift a case or two. What I didn’t expect was the guy to be waiting for me outside my rental with the trunk already open, wearing gloves, and asking which bags had fragile lenses. He’d checked the note I’d left. Already I felt like I was dealing with someone who actually read the job before showing up.
The car itself was spotless. Not flashy — just warm, comfortable, and functional. It had more than enough space for my gear, a few extra blankets in case I needed to wrap anything sensitive, and even USB-C charging which saved my butt later in the day when my phone dipped below 10%. But beyond the basics, what stood out to me most was just how calm the entire ride was. Aspen gets hectic, especially in peak season. Roads get jammed, parking disappears, events run over. But this guy? Unfazed. Adjusted on the fly, kept things flexible, and always had a backup plan if we needed to reroute or stall a few minutes. That kind of adaptability is rare.
How Better Transport Made My Photography Work Better Too
After that day, I started using them for every major gig. And I noticed something unexpected: my work got better. Not because I suddenly got more talented, but because I was less stressed walking into each job. I wasn’t arriving flustered or scrambling to unload gear in front of a busy lodge. I wasn’t worrying about whether I could get the rental car back to the lot before close. I just showed up, focused, and did what I was hired to do.
I mentioned this to a videographer friend who was heading into town for a multi-day shoot, and he asked me if the cost was worth it. I told him it depends on what you value — if you care about showing up prepared, keeping clients happy, and having a clear head to do creative work, then yes. 100%. We’re used to hacking everything to save a buck, but sometimes the hack is just hiring professionals and letting them do what they’re great at.
Why I Now Recommend This Service to Clients and Friends
Eventually, I started recommending the service to clients too. One of my couples was flying in their parents for a winter elopement and didn’t want them driving in the snow. I gave them the name and they booked it immediately. They ended up raving about the driver afterward and said it was the only part of the day that didn’t feel like it required 15 backup plans. That’s what made me realize this wasn’t just helpful for me — it actually raised the bar for the entire event experience.
And honestly, I’ve worked with plenty of transportation companies over the years. Most are either way too impersonal or way too into themselves. Either it’s just a dispatch number and some guy who barely speaks or it’s full-on tuxedo service that makes you feel weird unless you’re dressed in black tie. What I like about Aspen Way To Go car service is that it sits perfectly in the middle — professional, local, efficient, but also approachable. They don’t need to put on a show. They just show up and get it done, every single time.
The Kind of Service That Becomes Part of Your Routine
My favorite moment might’ve been last month, though, when I had an early morning sunrise shoot planned on the edge of town — icy roads, pitch black, and gear that couldn’t handle another bounce in a trunk. My driver showed up five minutes early, helped me quietly load everything, and even brought an extra thermos of coffee because “sunrise shoots are brutal.” That’s when I realized this had gone beyond just a hired service. These folks actually care. And in this town, that’s saying something.
If you’re trying to book, just go to AspenWayToGo.com — don’t overthink it. They keep things simple, and I appreciate that. No drawn-out process, no upsells, no weird hidden fees. What you see is what you get, and what you get is really solid service. It’s the kind of reliability that lets you focus on the stuff that actually matters.
Whether you’re a creative working the event circuit like me, a couple planning something unforgettable, or just someone visiting who doesn’t want to spend half their trip figuring out how to get from point A to B, this is the way to go. Literally.
I don’t rave about companies often. Most come and go, and the service is fine but forgettable. But every once in a while, you come across something that just works — not in a flashy way, but in a way that makes your life noticeably easier. This is one of those rare finds. I’m not going back to juggling rentals and guessing routes. I’ve already got my next three dates booked, and I’m never looking back.
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