ChatGPT Planned My Ski Trip. Here’s What It Got Wrong.

The mornings are frosty and flannels are back in rotation, which means skiers are pulling their gear out of storage and obsessing over ski pass options. I’m no different. I just scored my first pair of Hestras (finally joining the club), secured my ski pass, and am dreaming up a ski trip with my little brother.

Last year, we chased storms through Banff and the Powder Highway, but this year, I’m looking for simplicity. And since everyone seems to think AI can do just about anything, I decided to put it to the test: Can ChatGPT plan a brother-sister ski trip from start to finish? And more importantly, could it do it well?

I asked, I reviewed, I clarified. Here’s how it went:

The Destination

My brother lives in Denver and I live outside of Telluride, so we needed a destination that is a doable drive or flight for both of us. (Doable for me is around four hours of travel time.) We also like to ski more advanced terrain when we’re together.

ChatGPT recommended Wolf Creek, Crested Butte, Aspen Snowmass, Copper Mountain, and Jackson Hole, calling out Wolf Creek and Crested Butte as the “best picks.” I dug in deeper, asking how much it would cost to ski these five resorts without a pass (my brother has an Ikon, I have an Epic), how much we should expect to pay for gas or flights and lodging, and which resorts tend to be quieter, with shorter lift lines.

At the end of my questioning, I came to the same conclusion ChatGPT had from the start: Our best bet in regard to equal travel time, terrain, and cost would indeed be Wolf Creek or Crested Butte.

My takeaway: AI is a great brainstorming tool. It’s great at coming up with ideas regardless of what requirements you throw at it. That said, I was surprised that it didn’t suggest any out-of-state options other than Wyoming. I was expecting it to recommend a few ski areas outside of Salt Lake City.

When to Go

My experience as a seasoned ski vacationer tells me that the best time to book a ski trip is an off weekend in January or February. But ChatGPT had other ideas.

It suggested visiting Wolf Creek as early as December, noting that it’s “One of the best places in CO for early-season powder. Terrain can be ~50–80% open by Thanksgiving.” Meanwhile, it suggested waiting until mid-February to book a trip to Crested Butte, noting that late in the season is when the extreme terrain often opens.

My takeaway: Impressed. It clearly gave the question more thought than I did, but just to be sure, I had to fact check the “~50–80% open by Thanksgiving” statement. The amount of open terrain at Thanksgiving varies by season, but Wolf Creek is often close to fully open around the holiday. Last season, for example, 100 percent of the mountain was open by Thanksgiving.  That said, early season is unpredictable by nature, so you’re taking your chances, to be sure.

Trip Planning

Here’s where things got a little muddy. When I asked for a list of winter lodging options in a moderate price range in and near Wolf Creek and Crested Butte, ChatGPT gave me a list of accommodations along with their distance from the ski area and estimated rates—but some of the facts were off.

For example, it suggested staying at the Alpine Inn in Pagosa Springs to ski Wolf Creek, noting it’s a 1–1.5 hour drive from the resort; it’s actually only 40 minutes. And in Crested Butte, it recommended the Nordic Inn, stating ambiguously that it is “likely in town.” In reality, Nordic Inn is located in the ski village at the base of the resort, not in the town of Crested Butte at all—a distinction that’s pretty simple for humans to figure out, but not so much for A.I.

Similarly, when I asked for a sample itinerary of what a four-day/three night ski long weekend at Wolf Creek and Crested Butte might look like, it gave me a great outline, but with a lot of incorrect details, including drive times.

My takeaway: ChatGPT is great at providing a general idea of what a trip could look like, but I wouldn’t trust it to literally plan your ski trip. You have to double check all the details—from hotel and lift ticket costs to drive times and restaurant recommendations. Pretty easy if you’re already a savvy ski traveler and can likely spot the inaccuracies; more difficult if you’re truly planning from scratch, as most destination skiers are.

The Cost

I asked ChatGPT to provide a budget for both me and my brother for our long weekend that includes lift tickets, lodging, gas, and food/entertainment. I felt like it gave us a good idea of what to expect, but I took the numbers with a grain of salt—especially after I asked the same question twice and it gave me two different answers.

My takeaway: When it comes to prices, which can vary greatly based on when you plan to ski, your car’s gas mileage, how often you eat out, and where you want to stay, ChatGPT can give you a general idea of cost, but not an estimate worth basing decisions around. And the fact that it changed its cost estimation the second time around tells me that it’s pulling data from different places each time—so you may be getting lodging costs from a blog post written five years ago.

The Verdict

I would use ChatGPT again to plan a trip, especially if I didn’t have an idea of where I wanted to go and needed to narrow down options. It is great at filtering out the noise in order to tailor suggestions to meet your needs.

That said, I’d skip it for sorting out details. I would rather talk to friends and scan Reddit to fill in my itinerary with après plans and hotel options, and would trust my own cost estimations over the ones I got from ChatGPT, because unlike pretty straightforward details like a resort’s vertical drop or skiable acres, hotels, restaurants, and bars can close or change hours or ownership, and you don’t want to make concrete plans based on potentially outdated info.

In other words, use it to brainstorm trip ideas and travel inspo, but don’t head out before fact-checking the most important details first.