My 7 Worst Travel Mistakes

“We don’t make mistakes, just happy little accidents” – Bob Ross

With more than 20 years of corporate travel and a few additional decades of personal travel, I can assure you that I have made some mistakes along the way. Some had little consequences and others, well, serious consequences, but the important thing is that I learned from each and every one. In the hope that I might impart some knowledge and lessen your chance of making the same mistakes, I am gladly and humbly sharing my 7 worst travel mistakes with you.

travel mistake

map la guardia jfk new yorkDuring one of my corporate trips, I had to select a layover city that wasn’t familiar to me. I decided to take an earlier flight than usual and was faced with going through New York. Big city airports don’t bother me, in fact, I much prefer them to smaller ones, as they offer more things to see and do during layovers. I made my selection of flights late one evening and I admit that I didn’t pay a lot of attention to the layover details. I was in a rush to book my flights and I multitasked work activities at the same time. When I arrived in New York, I had about a 3-hour layover before my connecting flight. I explored La Guardia airport and an hour before boarding time I slowly walked over to my gate. When I arrived I notice the information panel listed the flight destination as Nantucket, however, I was headed to Atlanta. I approached the counter and asked if the gate had changed for the Atlanta flight. The agent asked to see my ticket and she looked up and told me that I was in the wrong airport! I had failed to notice that although I arrived in La Guardia, my second flight was taking off from JFK airport, 12 miles away. Fortunately, she was able to rebook me on the next flight out of La Guardia but I lost 5 hours waiting for my new departure.

To avoid mistake # 1 – Be very careful to check the details of your layovers, especially in cities with multiple airports. 

Another time I had booked my flight through an online travel site. The entire site had screens with drop-down menus. Again, multitasking, I accurately selected San José as the city, but somehow I selected the second San José. The city I wanted was San José California but I selected San José Costa Rica as my destination. I did find the flight was more expensive than usual, but at the time, flight costs greatly fluctuated. I was fortunate to notice the error the moment I printed my tickets, however it took me more than an hour on the phone to fix the issue.

To avoid mistake # 2 – Be very careful to select your flights or hotels carefully, especially when dealing with pull-down menus. 

I arrived very late at night in a city unknown to me. As I entered the cab I told the driver to take me to the Marriott Hotel. He quickly interrupted me and told me it would be a 20-minute ride. I told him to go ahead and I relaxed as we headed to the hotel. When I arrived there were many people waiting to check in, but I waited patiently for my turn. As I handed over my passport and credit card, the hotel clerk asked me a few times to spell my last name. He couldn’t find my reservation and told me the hotel was full. I haded him my printout and he quickly told me the Marriott hotel that was booked was the OTHER Marriott hotel 45 minutes away. Needless to say, I wasn’t a happy traveler. 2 hours later I finally laid down in my hotel bed to get a few hours sleep before my very early morning meeting.

To avoid mistake # 3 – Ensure you give ALL the hotel information to your driver, including the actual address. 

It was a Friday night and I was excited to get back home for the weekend. I was leaving my work location where a major football game was being held. All the hotels had been booked months earlier. Because of the type of arrangement we had with our hotel, I had the option to extend my stay but it had to be done at least the day before the extension was needed. I checked out and headed to the airport only to find out that my flight had been canceled. I had a new cell phone and had forgotten to update my traveler profile with my new number. I also had checked the flight status a few hours before my checking out of the airport and my flight was on time. Somehow, between my last check and my arrival to the airport, my flight was canceled due to mechanical difficulties. The airline was unable to rebook me until the next morning but they agreed to find me a hotel room for the night. Turned out every single hotel in the city or nearby areas was fully booked. The closest hotel was 2 hours away and I wasn’t keen on staying all night at the airport. Turned out I lost an entire day due to that unfortunate situation.


To avoid mistake # 4 – Ensure you keep your travel profile up to date, with your latest numbers and email information. Always check your flight status closer to the time of your departure for the airport. 

I often traveled during the busiest business travel times; Monday mornings and Thursday or Friday late afternoons. I, like many others, traveled with a carry on suitcase to avoid having to wait for my luggage. Often on commuter planes, we are asked to place our luggage (even carry on) on the jetway as we are boarding our flight, to later recover the suitcase at our arrival. If you’ve ever been on a flight with many business people, you might notice that many have similar black carry on suitcases. They look very alike, especially at night. Turned out someone grabbed my suitcase by mistake and left before I noticed my suitcase hadn’t been brought to the jetway. I checked on the carousel to see if it hadn’t been added to the regular luggage and figured it hadn’t made it to my plane. An agent checked my luggage tag only to let me know it had been unloaded with all the other carry-ons. We found a similar carry on left on the jetway and realized the owner of that suitcase took mine by mistake. The next day the airline called stating my suitcase was taken by mistake and was returned to the airport. I received it that same afternoon.

colourful suitcases

To avoid mistake # 5 – Lots of suitcase look alike. Add some bright bows or ribbons or stickers to differentiate yours, or buy a bright pattern or colour not often seen.

During my walk across Spain on the Camino de Santiago, I used my debit card in a bank machine and just as my money was about to be given out, the power went down in the area. Given this was on a Sunday and the bank was closed, I needed to wait until the morning to return to the bank to get my card and my cash.

To avoid mistake # 6 – The chances of this happening to you are slim, but just in case, bring along a backup credit card or debit card. 

When I traveled for work I always paid by debit card or my corporate credit card. Chances are what happened to me will almost never happened to you, but it served as a lesson for me. On August 14th, 2003 the Northeast blackout of 2003 was a widespread power outage throughout parts of the Northeastern and Midwestern United States and the Canadian province of Ontario. I had just landed in Newark New Jersey to connect to my flight to my hometown of Ottawa. Little did I know that I was part of that big blackout. The airport ran on their generators and after more than 8 hours, the airlines finally arranged to find out hotel rooms out of town. When I got to the hotel I had no way to pay as all the cash machines and the credit card machines were down. I couldn’t even pay dinner in cash as all I had were a few dollars. Given the extenuating circumstances, the hotel took prints of our credit cards, and the next day buses were waiting for us to bring us back to the airport. I managed to get onboard a flight to Montreal (one of the only ones available) and the rental car company arranged for me to drive one of their cars to the Ottawa airport, only because it hadn’t been checked in. I made it home, without my suitcase and very hungry!

cash money

To avoid mistake # 7 – Always have some amount of cash on hand in the local currency. Best to have it and not use it (it can always be reconverted) than not have it and be stranded as I had been.

I’m sure that if you have traveled you likely have a few, as Bob Ross calls, happy accidents.

What did you learn while you traveled?


Retired exec consultant who traveled for more than 4 decades, both corporate and leisure. I appreciate my travel experience and want to share tips, photos and stories with readers! I live in Ottawa Canada and have traveled to 31 countries.

2 thoughts on “My 7 Worst Travel Mistakes

  • February 3, 2018 at 4:25 am

    Thanks for the tips! I look forward to using them the next time that I travel.


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