My 4 Most Frustrating Travel Fails of 2019

by Lyle Daly | Updated July 21, 2021 - First published on Feb. 29, 2020

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Frustrated Traveler

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I made some amazing memories during my travels in 2019 -- but I also had my share of annoying screwups.

I made some amazing memories during my travels in 2019 -- but I also had my share of annoying screwups.

Since I spent 2019 living in several different cities, I got to do quite a bit of traveling. For the most part, this went well, as I enjoyed all my trips and didn't have any truly disastrous experiences.

There were, however, some moments where I was kicking myself for making bad decisions. To help others learn from my mistakes, here are the most frustrating travel fails that I had last year.

1. Taking too much luggage

This is traveling 101, and I should have known better. When I first moved from the United States to Colombia, I took one piece of carry-on luggage and two checked bags. That put me at the limit of the business class baggage allowances, and I didn't need to pay any extra baggage charges.

There were two problems, though. The first was that it was extremely inconvenient anytime I needed to move that much luggage from one place to another. And the next time I flew, my girlfriend and I had one bag more between us than allowed, resulting in an additional charge of about $50.

Since then, I've consolidated down to a carry-on and a checked bag. Had I been smarter about what I took with me in the first place, I would've saved a bit of cash and the headache of having so many bags.

2. Booking a terrible Airbnb at the last minute

There's always a trade-off when making travel plans. Do you set everything up in advance, sacrificing flexibility for stability, or do you keep your options open? I usually go with the latter, but this has come back to bite me.

One such situation was when we needed a place for a week at the last minute, so I booked an Airbnb that seemed acceptable for a short stay. Oh, how wrong I was. Although this apartment was listed as having two bedrooms, one "bedroom" was just a hallway that had a bed shoved in it, blocking the bathroom door. The internet connection was unstable. And not only was it filthy, it also had roaches to complete the nightmare rental experience.

We had to suffer through one night there because there were no other options, but we left the next morning.

I learned two important lessons from that rental:

  • Try to book places at least a few weeks in advance, because it's stressful and difficult to find a good option at the last minute.
  • Never trust lukewarm vacation rental reviews. If reviews are short and only say things like "nice place" or "good communication," those aren't exactly ringing endorsements.

3. Picking the hotel that didn't offer free breakfast

After that Airbnb experience, I figured I'd book into a hotel for the remaining days. I booked a place using the travel portal from one of my credit cards, and after comparing a few options, I picked one that looked the nicest.

Upon arrival, I learned that there was an extra charge for breakfast every day. That was an unpleasant surprise, especially since I was sure the listing online had said "complimentary breakfast." But when I went back to look, I realized that it actually said "continental breakfast."

Of course, I also had to check if the other hotel I was considering had free breakfast, and it did.

While the breakfast wasn't super expensive at $10 per person, it still added $60 to my bill at checkout.

4. Arriving at the airport too early

Arriving early to the airport may not fit the typical definition of a travel fail, but it does when the airport is under construction and there's nothing to do.

My logic wasn't actually horrible. I didn't want to worry if there was any traffic on the drive to the airport. Even though this was a smaller airport, I figured it may still have a comfortable airport lounge to pass the time until the flight.

Once again, I was way off base. We arrived about two hours early, but airport personnel didn't let anyone on our flight go through security until 45 minutes before the scheduled departure time. The only snack option was a small minimart, and after we finally went through security, there was absolutely nothing to do except sit and wait.

What to take from my travel fails

As frustrating as these issues were at the time, they were also good reminders of the following:

  • It's not worth it to take too much luggage. You have more to move, you may need to pay extra baggage fees, and the only benefit is taking along things that you probably don't need.
  • Give yourself plenty of time when booking vacation rentals and hotels so that you can be selective about which you choose.
  • Read carefully when you make any sort of travel booking to confirm that you're getting what you want.
  • If you're planning on spending time at the airport, check what it offers first and bring something to do while you wait.

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