Traveling with family is never simple. Especially when it’s not just you and the kids, but you, the kids, your spouse, your in-laws, and about seven different sets of expectations. I’ve planned a lot of vacations before — quick beach trips, a couple city getaways — but nothing like trying to organize a multigenerational winter trip to Aspen. My wife had been wanting to take the kids skiing for years, and my mother-in-law kept saying she wanted to “see the Rockies before her knees give out.” So I finally bit the bullet, picked a week in January, and started planning.
I thought the logistics would be the easy part. Flights, hotel, rentals — I figured if I booked early enough, I’d be ahead of the game. What I didn’t realize is that Aspen is beautiful and magical and absolutely not the kind of place where you can just show up and expect things to work themselves out. Especially not when you’re traveling with a group that includes a toddler, a grumpy teenager, and two retirees who need to know exactly where the bathroom is every 45 minutes.
The real headache started when I began figuring out how we were going to get around. We were flying into Denver, because it was cheaper and had more flight options. I assumed we’d just rent a car — or maybe two — and drive the four hours to Aspen. I even had the idea that we’d stop along the way, grab lunch, take in the scenery. But as the date got closer, I started reading the fine print. Winter road conditions. Chain laws. Narrow, steep passes. All the kinds of phrases that make your stomach twist when you think about driving a rental full of family members through icy mountain roads.
So I started looking into alternatives. Shuttles sounded convenient until I read that they often meant sharing with strangers and following a fixed route. With kids and my in-laws? No thanks. Ride shares were too unreliable, and none of the car rental options guaranteed snow tires. I spent way too many nights up late reading reviews, checking forums, looking for something — anything — that wouldn’t make this trip start off stressful.
Eventually I came across a small transportation company that didn’t look like a national chain or some overly fancy celebrity-level thing. Their site was simple, kind of plain, but the reviews stood out. All these comments from real people, not bots or marketing fluff — families, couples, even solo travelers who all said the same thing: they were professional, on time, and most importantly, they knew the mountains. That last part sold me.
I emailed them, explained our situation, and got a reply the same day. They asked about our flight times, how much luggage we’d have, whether we needed car seats, and even if anyone in the group had motion sickness (they adjust the routes when they can, apparently). I hadn’t even thought of that. It was the first time in the whole planning process I felt like I wasn’t doing this completely alone.
The driver met us right outside the airport in Denver. SUV was spotless, warm, and roomy enough for all of us and our overpacked luggage. My daughter immediately fell asleep once we got rolling, and my son had his headphones on within minutes. My in-laws were comfortable, which is saying something, and my wife actually leaned over halfway through the ride and whispered, “This was the right call.” I agreed.
We didn’t hit any major weather, thankfully, but the roads were still slick in places, and I was so relieved not to be the one behind the wheel. Our driver knew exactly when to slow down, when to change lanes, when to avoid certain exits. He even gave us a heads-up about which rest stops had decent coffee. I know that doesn’t sound like much, but after traveling with family for 12 hours, good coffee becomes borderline sacred.
The drive into Aspen was stunning. Snow-covered trees, winding roads, the kind of views you only see in Christmas movies. We pulled into the resort without a single moment of tension. No one was carsick, no one was arguing about directions, and I didn’t have that familiar travel anxiety building in my chest. Just a smooth ride, a quiet car, and the knowledge that everything — for once — was actually going according to plan.
We used the same company again later in the trip when we needed to get into town for dinner and then again to get to the sledding hill one afternoon when the grandparents didn’t feel like going out. Each time, the driver was early, polite, and totally unfazed by our semi-chaotic crew. One afternoon we had to change the pickup time because my son dropped his glove off a ski lift (don’t ask), and they adjusted without a problem. It just felt… easy. That’s not something I ever say when we’re traveling with this many people, but it was.
I think what really struck me was that it didn’t feel like a “service.” It felt like someone who had our backs. Someone who understood how unpredictable travel can be, especially with a family, and made sure the ride wasn’t one more thing we had to worry about. There was no pressure, no sales pitch, just real help from someone who knew the town, the roads, and the rhythm of Aspen better than we ever could.
By the time we were heading home, even my notoriously picky father-in-law said, “Let’s use the same company next time.” That might be the only time in my life I’ve heard him suggest using something twice.
If you’re planning a trip to the mountains and thinking of just figuring it out when you land — don’t. Especially if you’ve got kids, or older parents, or honestly just want your vacation to start without stress. Find someone local who knows the terrain, who shows up when they say they will, and who makes it feel like you’re not just another booking on a clipboard. For us, this Aspen car service did exactly that.
It’s funny — I spent hours researching the lodge, comparing ski rental packages, even picking the perfect restaurant for my wife’s birthday dinner. But the part of the trip I’m most grateful for? The ride. Because that’s what set the tone. That’s what made the whole trip feel like something we’d actually want to do again.
I’ll probably never be one of those people who just “pops over” to Aspen for a quick ski weekend. It’s a process, especially with family. But after this experience, I get why people come back. And when we do, I already know how we’re getting there. Because when it comes to aspen private transport, there’s no need to overthink it. We already found what works.
