My 5 Most Cringe-Worthy Travel Fails, From Missed Flights To Wrong Hotels

by Gary Leff on October 7, 2024

I do pretty well in travel but also make my share of mistakes, mostly out of habit or path dependence. Since I know how things ‘usually work’ I don’t always pay attention to schedule changes. And I don’t pay attention to the details of my reservations – I’m on auto-pilot, I know that when I land in a given city I ‘always’ go to the same hotel. If I booked a Hyatt there, it must be my usual one!

Here are the (5) biggest mistakes I’ve made in travel, though each one worked out just fine. I thought I’d share these to show my own fallibility, I know the correct advice and should always follow it but I am… human.

Showing up at the airport in the afternoon for a morning Sydney – Los Angeles flight Virgin Australia had changed the flight time months earlier, which at some level I knew, but Delta (who issued the award tickets) hadn’t notified me of the change. Delta re-booked me onto their own non-stop the next day in business class (revenue inventory) and Virgin Australia gave me a hotel room for the night.
Snuck into a United Airlines club lounge when my ticket would have granted me access anyway, only I didn’t realize it. That was over 20 years ago and I still feel rather dumb for it.
Showed up at the Novotel Bangkok Suvarnabhumi hotel only to learn I’d made a reservation for the following month they simply moved my prepaid booking ahead.
Drove to the wrong Hyatt in Miami out of sheer habit, I’d simply gotten used to staying at the Hyatt Regency Coral Gables. To save me the hassle of changing hotels they simply transferred my booking and I wasn’t treated as a no show at the other property.
Let my AAdvantage miles expire when I was a teenager. I’d accumulated about 20,000 miles from a trip to Australia (I flew American back when they served Sydney via Honolulu with a DC-10) and when I went to credit a trip to Florida I learned my account was no longer active. I didn’t re-join the program for about 5 years, and though it wouldn’t benefit me in any way I still wish I had my original account and joining date.