How an Aspen ski vacation gone wrong ended with my family in the police station

Jan 4, 2020

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It was the perfect plan.

We were going to spend a family vacation skiing and snow tubing in Aspen Snowmass for a few days in late December and early January. We had booked the slopeside Westin Snowmass with Marriott points, our Marriott suite upgrade nights cleared and we had United flights booked directly in and out of Aspen. We didn’t even need a rental car since the hotel offered an airport shuttle. It was simple, old-fashioned, mountain family fun. At least, that’s how it appeared on paper.

(Photo by Summer Hull/The Points Guy)
(Photo by Summer Hull/The Points Guy)

And it really was classic winter family fun. At least until all four of us ended up in the Vail police station.

This tale of travel plans gone awry will seem bizarre and even unbelievable at times. But it’s an important reminder that even the best-laid plans can be cancelled, snowed out or hauled away in a police cruiser — and that having a Plan B isn’t always enough. So, strap on your snowshoes.

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View from the Westin Snowmass (Summer Hull/The Points Guy)
View from the Westin Snowmass (Summer Hull/The Points Guy)

A snowballing situation

Other than a five-hour flight delay getting into Aspen, the trip started off well. The suite was extremely nice for the 35,000 Marriott points per night we paid, the Snowmass skiing courtesy of our annual Mountain Collective Passes was quite good, the sun was out and my oldest daughter even starting skiing blue runs with me.

But the day before our flight home, I checked in for our flight and looked at the weather. The forecast? Snow. Lots of snow.

Snow is great for ski towns in the winter, but it isn’t great for those hoping to fly in and out of smaller airports like the one you’ll find in Aspen. I immediately knew the next travel day probably wouldn’t go as planned, so I booked a speculative one-way car rental for the next day to drive the couple hundred miles from Aspen to Denver (DEN) as a Plan B, just in case our flight got cancelled.

Related: Things to know about Colorado’s new winter traction law

Surprising exactly no one, our flight home from Aspen (ASE) to Houston (IAH) was in fact cancelled due to weather. Because flights around the New Year were packed full, United didn’t have confirmable space on any other planes out of Aspen for at least five days. Five!

There weren’t many hotel rooms available in the area, either, and certainly none available on points or at affordable rates. There was, however, an afternoon break between snow storms, so we picked up our SUV rental from Hertz and decided to drive toward Denver, where both flights and hotel rooms were in greater supply.

We made it 90 miles, or as far as Vail, before night fell, the snow returned and we hit major traffic courtesy of accidents and deteriorating road conditions.

When it became clear we had to stop soon, we booked the last room in the area with two beds at the Vail Marriott Mountain Resort. The cost? A cool $1,000 for the night. It was peak New Year’s Day ski season for Vail, so prices were exorbitant everywhere.

Vail Marriott (Summer Hull/The Points Guy)
Vail Marriott (Summer Hull/The Points Guy)

Luckily, I didn’t have to stress too much about the cost, as it was only for a night and our Chase trip delay insurance should cover up to $2,000 in trip delay expenses (up to $500 per airline ticket, for four tickets booked).

After a decent night’s sleep — in what turned out to be the most expensive hotel room I’d ever slept in — we started the next day optimistic and ready for our new early afternoon flight home from Denver. It was still snowing and the roads weren’t great, but at least the sun was out and we had allotted several extra hours for the drive from Vail to Denver.

Related: Credit cards that offer trip delay coverage

When the backup plan fails

Just two miles into the drive, on I-70, the rental car lost all power and the engine died.

Luckily, we were passing a truck chain-up area when this happened, so we coasted between 18-wheelers on the side of the road. Less lucky? We were now in a car that wouldn’t drive and smelled awful. I’m no mechanic, but something was clearly broken.

I started making calls and got through to the roadside assistance number for Hertz who agreed to send a tow truck. That truck didn’t arrive for about four hours.

While trying to figure out our next move while sitting in a stalled car on the side of an icy road, several very large vehicles lost control near us and started sliding. Thankfully, they didn’t hit us, but I quickly decided we had to leave the car. The problem was we couldn’t see anywhere to go, the temperatures had plummeted to single digits and it was still snowing.

Oh, and our 4-year-old was now feeling nauseous. Because, of course she was.

Just before we began digging through our luggage for ski gear to start hiking, I called the Vail Police Department and asked for help or advice.

(Summer Hull/The Points Guy)

Minutes later, I was loading my kids into the back of a police car — after the little one finished throwing up into the snow on the side of the road.

My husband stayed with the broken rental car for an hour or two, optimistically waiting for the tow truck, until the same officer returned for him and all our nine bags.

We were safe, but we were stuck in a police station … which was quite obviously a far cry from the slopes of Aspen.

There were no rental cars available, no room on any bus or shuttle service into Denver, no Ubers available and no way to get the four of us into Denver and onto a flight home — not for the next four days.

Desperate measures

I zeroed in on a new possibility: There was one flight with four seats available that evening out of Eagle County Regional Airport (EGE), about 30 miles away. The seats were in first class on Delta going through Salt Lake City (SLC) for about $5,000 for the four of us.

I was desperate, but I wasn’t suddenly desperate and rich. We were already well over $1,500 into our Plan B, which will hopefully be reimbursed. But there are never guarantees until it happens.

While a police station isn’t the Four Seasons — that’s actually located just across the street — we weren’t in some awful location. But we were now late for work, out of clothes, exhausted, stressed and traveling with a sick kid. Basically, we were all just ready to just be home.

With distress surely evident in my voice, I called United from the police station. I asked for any flight out of the nearby Eagle airport, since we simply couldn’t get to Denver as I’d hoped. At first, I was told it would be days until a flight had availability out of Eagle. I then asked specifically for seats on the Delta flight for sale on Google Flights and Delta’s website.

That was also a no at first, too, but then I started telling our story. It just came out. I couldn’t stop it.

Related: What’s new this ski season

My daughter with the Vail Chief of Police (Summer Hull/The Points Guy)
My daughter with the Vail Chief of Police (Summer Hull/The Points Guy)

Our original Aspen cancellation was a weather-related issue, and I was asking for seats on another airline in first class. It was a stretch and, up to this point, the airline hadn’t really helped much after cancelling our original flight home. But it never hurts to ask, right?

I was put on hold and, with nothing short of a holiday miracle, the agent made it happen. I might have cried. OK, I totally cried. We had a way home — at least, if we could make it to the airport.

That was doable, but still not simple. After Ubers kept cancelling our requests, I Googled a local taxi service in Vail. I called the first one I saw and asked for a ride to the airport for four people and a lot of bags.

“It’s a long story,” I said, “but we’re at the Vail police station.” (I totally assumed he was going to say, “Um, no.”)

Instead, the driver, Jon, immediately said he was on his way in an SUV with snow tires. It wasn’t going to be a cheap ride (read: $200), but I was immediately grateful since it would represent progress. He was kind, and even texted us later to make sure we got home safe.

Try, try again

During the drive to the airport, I saw that United was now selling three seats on a nonstop flight that afternoon from Vail to Houston. Since we were now ticketed on Delta, it wasn’t a simple change but, after a few more phone calls, the girls and I got into the last row on that flight. My husband was moved to the last seat on a connecting United itinerary a couple hours behind us, but ahead of the Delta flight.

With inches of more snow on the way, we just wanted out of the mountains. Thankfully, this time, the plan worked.

(Summer Hull/The Points Guy)
(Summer Hull/The Points Guy)

Lessons learned

I know what you’re thinking: How bad can a few extra days in Aspen really be?

But I’ll tell you that, in a broken down car, on the side of an icy road, with massive trucks skidding toward you and no clue how to get you and your kids home without spending thousands of additional dollars, it can be pretty bad.

So many things went wrong, but there was also quite a lot that went right. Perhaps most importantly, we encountered good people willing to help, and we never gave up.

The usual tenet of being extremely proactive in the event of airline delays and cancellations was certainly true here, but continuously checking flight availability from numerous area airports; setting Expert Flyer alerts; and quickly and persistently asking for the help we needed were all important measures. If we accepted the initial “no” answers we got from the airlines and Uber drivers as final answers, we would still be in Colorado.

In the future, we’ll continue to book flights with credit cards that offer the best trip delay coverage and, despite the temptation to save a few hours when things go as planned, we will also strongly consider avoiding mountain town airports that are prone to cancellations during severe winter weather. The latter is especially true during peak travel times when back-up options will be harder to come by.

For example, currently available Bureau of Transportation (BTS) statistics for 2019 indicate that departures and arrivals at Aspen’s airport are only punctual 62% and 66% of the time. Even worse is the 7.55% cancellation rate. I suspect winter-specific data points are more grim.

Related: Booking ski trips with points and miles

Snow is fun until it’s time to leave (Summer Hull/The Points Guy)

Denver International, on the other hand, had a cancellation rate of just 1.78% in 2019, and there will be far more seats available when cancellations do happen in Denver than what you’d find in Aspen.

At the end of the day, we got home safely and made memories — perhaps too many memories, but memories all the same. We love the mountains and will keep taking ski trips, but perhaps in a strategically different way next time.

And, hopefully, this is the last time I’ll see my girls in the back of a cop car.

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