This Travel Mistake Almost Forced Us to Spend Our Anniversary in a Rental Car

Sep 4, 2018

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I travel a fair amount each year, often with multiple trips to different places every month. For this reason, I have routines I follow when researching travel dates and locations. But every system has its flaws, and I discovered a major flaw that almost ruined my anniversary trip to Telluride. It’s called human error.

This year, to celebrate our 10th anniversary, my husband and I wanted to get away to somewhere with cooler weather. After some debate, we decided on Telluride, Colorado. My family has had a special connection with Telluride for generations, but I hadn’t been in over a decade and Josh had never visited this special spot.

The stunning mountains, walkable historic town and comfortable 40 to 60 degree average temperatures in early September sealed the deal. The bed and breakfast property we’d been eyeing was available for our dates, and flights were quite reasonable from Houston’s George Bush Intercontinental Airport (IAH) to Montrose Regional Airport (MTJ), which is about 90 minutes from Telluride.

View from the Telluride gondola
View from the Telluride gondola

Where things went wrong

I let Josh know what I found, and we both agreed to book the trip to Telluride for the big anniversary celebration. This back and forth happened by phone and by text while I was in New York City preparing to launch TPG Family back in July. As you might imagine, things were a bit, er, hectic.

As soon as we agreed on the specifics I booked our flights. But before I could get to the hotels, I got distracted with work, and didn’t return to booking hotels for a day or two. When I searched that time, the bed and breakfast was no longer available. I did a larger search for the area on to come up with an alternative, and there was virtually nothing that worked for us. As in nothing. At. All. was showing that Telluride was 99% booked, and what was left was around $1,000 per night and up with a three day minimum. That was not at all what I was seeing when I did my spot checks for hotel availability before I booked flights.

Turns out, human error was a factor. I was in a rush, and had searched the correct weekend for flights, but accidentally searched the weekend before for hotels. Getting a hotel the second to last weekend in August in Telluride was no big deal. However, the last weekend in August (also the first weekend in September) was — unbeknownst to me — the annual Telluride Film Festival. This is, as it happens, a very big deal with A-list celebrities, film industry folks and film buffs flocking to the very small mountain town and booking up any and every available room, basement, inn, house and probably even some camp sites.

By the time I realized my mistake, our flights were already past the 24-hour free cancelation window. Not only that, but we had grandparents flying down to watch our kids that weekend, and we very much wanted to go to Telluride, whether Emma Stone, Nicole Kidman and Robert Redford were there or not.

Every day, multiple times per day, I checked hotel availability and as the date crept closer, the situation was not improving. A few weeks went by and we still had found nowhere even remotely acceptable to stay. Things were looking so bad that when we locked in our car rental we booked a large SUV so we could sleep in it if we had to: true story.

This could have been where we spent our anniversary…in the car.

I’m not kidding even a little when I say I thought we would probably end up camping in our car. But I’m not really the camping type, so this was the “hell or high water” plan. (And hell and high water — read: Hurricane Harvey — was exactly what ruined our anniversary trip last year.) We were going to Telluride whether we had a hotel or not.

In the middle of all of my hotel searches, I reached out to the bed and breakfast where we really wanted to stay and asked them to please keep us in mind if anyone canceled for the weekend of the film festival. I highly doubted that would ever happen, but it’s free to ask.

And then, just as we were starting to consider nonrefundable, over-priced and utterly mediocre properties miles and miles away from Telluride, I got an email from the Dunton Town House in Telluride: the place we really wanted to stay.

They had a last-minute cancelation for our dates and offered the room to us at their regular holiday (in this case, festival) rate.

Compared to the insane prices I was seeing for poorly rated properties (and compared to the joys of sleeping in the rental car), this seemed like winning the jackpot. We later learned that a production company had rented out several of the property’s five rooms, and then decided not to attend the festival. Their loss was very much our gain.

Dunton Town Home breakfast area
Dunton Town Home breakfast area

Don’t make the same mistake

I know to check flight, car rental and lodging prices before booking anything non-refundable, assuming I have travel date or location flexibility. I followed that booking method for this trip, but I was careless, and my hotel search was one weekend off. That small but simultaneously massive error could have easily forced my husband and I to spend our 10th anniversary camping in an SUV.

This time, we also got really, really lucky. We held off from making other plans and just kept hoping and checking. Reaching out to the property never hurts, and in this case, it’s what saved the vacation. If you ever find yourself in a similar situation, don’t be shy about establishing a connection and sharing your story — especially if you’re interested in a privately-owned property.

It is also a very good idea to check local event calendars before falling in love with a destination, especially where lodging options are limited, such as Telluride.

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