Planning the Aspen Adventure
I’d never been to Aspen before. Never skied either, unless you count that one time in college I slid down a bunny hill in Vermont and ended up on my back. So when my girlfriend told me she wanted to go to Aspen for her birthday—like, really go, not just talk about it over wine—I wasn’t exactly sure what I was signing up for. I’d been to Colorado once, years ago, but Aspen felt like a different world. Everyone talks about it like it’s all champagne bars and ski boots, so I figured, why not? Let’s do it.
She handled most of the planning. Found a little lodge near downtown, picked the restaurants, even booked a snowmobiling tour. But when it came to getting there, I kind of dropped the ball. I just assumed we’d land, grab an Uber or something, and be on our way. Easy. But no one tells you how wild the logistics can get in the mountains, especially if you’re flying into Denver like we were. We didn’t even land that late—just after noon—but it had already started snowing by the time we grabbed our bags.
No Ubers, No Problem
There were no Ubers. None. I’m standing outside the terminal, phone in my hand, freezing, just watching the little circle spin on the app. Everyone else seemed to have rides already waiting. I was starting to feel pretty dumb. That’s when she pulled out her phone, smiled like she knew something I didn’t, and said, “Don’t worry. I booked a car.”
Apparently, she’d looked into it days earlier and figured I’d forget. So yeah—she had it covered. Five minutes later, a black SUV rolled up with our name on the dashboard. I’d never been so relieved to see a car in my life.
The driver was calm, friendly, and totally unfazed by the snow that was now picking up speed. I was trying to play it cool, but inside I was pretty sure the mountain pass was going to be terrifying. It wasn’t. He handled it like he’d done it a thousand times—and I’m guessing he had. The roads were narrow, sure, but the tires were legit, the ride was smooth, and the car was warm. And clean. That kind of clean you only get from someone who actually cares.
A Scenic and Comfortable Ride
It took a little over four hours to get to Aspen, but it didn’t feel that long. We stopped once for coffee, and the rest of the time we just kind of zoned out, looking out at the snow-covered hills and occasional elk crossing. The driver knew exactly where to go, where to avoid traffic, and even pointed out a few spots along the way—small towns, scenic points, places people usually drive past without noticing. It was more like being guided in than just dropped off.
Turns out the company she booked with was called Aspen Way to Go. I’d never heard of them, obviously, but after that trip I started paying attention. We saw their cars a few more times during our stay—always sharp, always on time, always calm in the middle of whatever chaos was going on downtown. One morning it dumped almost two feet of snow overnight. A few other guests at the lodge were scrambling to figure out how they were getting back to the airport. Not us. Our ride was already scheduled, confirmed, and sitting warm out front with time to spare.
Exploring Beyond Aspen
We ended up using them a second time during the trip. Not even for anything major. Just wanted to get out of town for a few hours, go check out this hot springs place someone recommended. Could we have rented a car? Probably. But why mess with it? Parking in Aspen isn’t exactly a dream, and I didn’t come all the way here to drive through winding roads in a car I don’t know with other drivers who maybe forgot how to handle snow. We called the same company, booked a car, and the same kind of experience played out again—easy, smooth, and just kind of nice.
The thing I noticed about this limo service—and I don’t mean like stretch-limo, prom-night stuff, just proper private car service—is that it didn’t try too hard. No weird tuxedo driver, no over-the-top energy. Just reliable, comfortable, and run by people who clearly know how to deal with tourists who are slightly out of their depth, which I fully was. But I never felt like I was being upsold or talked down to. If anything, it felt like they were quietly making sure we didn’t make dumb decisions without ever saying it out loud.
Why I’ll Always Use Aspen Way to Go
By the time we flew home, I felt like we’d figured out a bit of the Aspen rhythm. You wake up early, beat the lines, ski till you can’t feel your legs, and then somehow find the energy to hit a bar or two before crashing into bed. And through all of it, the one thing I never had to worry about was getting around. That’s kind of a rare thing on trips like this. Usually there’s one moment where transportation becomes a headache—missed bus, delayed shuttle, that kind of thing. But not this time.
We’re already talking about coming back in the summer. Apparently Aspen’s just as good—if not better—when there’s no snow on the ground. Hiking, mountain biking, paddleboarding… I’m game. And you better believe I’m not messing around with random rides when we go. She’s already joked that I lost transportation-planning privileges permanently. Honestly? I’m fine with that.
If we’re coming back, we’re booking the same company. Same everything. Maybe even the same driver if we can request it. The guy was that good. I’ve taken plenty of trips where the transportation part felt like a necessary evil—something to just survive. This time it actually made the trip better. It set the tone from the moment we landed and took the stress completely off the table. That alone was worth it.
So yeah, for a first-timer in Aspen, I got lucky. Could’ve easily started the trip stuck outside an airport trying to flag down a car that never comes. Instead, I slid into a warm seat next to someone who actually planned ahead for once. That first ride into the mountains changed the whole tone of the trip, and I don’t think I’ll ever do it differently again.
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