There are certainly more travel savvy folks than I, but I do like to consider myself on the very experienced side of the spectrum. I’ve lived on three continents, visited close to 40 countries, and faced about every situation possible when it comes to the logistics of getting from point A to B. Today, I’ll share how after even all of that travel, there are times when I fail miserably.

The Late Show

Last year I was visiting Kuala Lumpur, Malaysia for business and was very proud I had located and booked the Le Meridien hotel which sits directly on top of Kuala Lumpur Sentral (that’s how they spell it) Railway Station. The KL Ekspress (I love the way Malaysians have made English their own) is a 25 minute train ride form the station to the airport. A perfect set up, right?

The morning of my departure, I thought I had planned which train to take from the Sentral station to the airport perfectly. However, I failed to recognize I was flying low cost carrier Air Asia X which has its own, new terminal and a reputation for being a mad house with long check-in lines, infrequent travelers, and strict time cut offs. Needless to say, my hour and a half arrival before my flight was not near enough time, and I quickly found myself behind a family of eight from Tajikistan apparently attempting to check in for a flight for the first time.

I ended up sprinting through the airport, cutting off people, forgetting there was a secondary security screening to get to the gates, chucking a just-bought $5 bottle of water across the security area to a trash can I think I caught out of the corner of my eye, and making it to my flight with the boarding door closing. I then only had seven hours of Air Asia X to look forward to.

Checked Baggage Rookie

In 2009, I won the US Navy-wide fantasy football league which scored me two tickets and an all expense paid trip to the Super Bowl XLIV in Miami. Problem was, the Navy planned this all very last minute and the only flight from Hartford, CT I could get included an overnight layover in Chicago.

At check-in in Hartford, I asked the agent to check my suitcase only to ORD so I could pick it up and have clothes for the night in the hotel. Upon landing at ORD, I confidently deplaned and strolled right out the doors to catch the hotel shuttle. I woke up the next morning looking for my suitcase in the hotel room when I realized I was a moron. I have never seen the suitcase since.

“Sir, there is no Business Class”

I once had a flight from Providence, RI to Chicago on United which was serviced by a small, regional Bombardier CRJ-200. At check-in I was handed a boarding pass which said economy. I was so confident I had used my award miles to book business class I began to argue (politely) with the check-in agent there was a problem.

I realized after I was done with my speel that the smug grin on the agent’s face was because she was waiting the whole time to say “Sir, CRJ-200s don’t have a business class.” I thanked her for her time and swiftly headed towards security.

Train Platforms Are Tough

Surely we’ve all played out this scene in the subway station of a large city: After you get through the main gate and find the train line you need, you have a decision to make. You can head up or down a set of stairs which lead you to one of two platforms servicing the same train line, each headed in the opposite direction. If you chose the wrong platform, you go in the opposite direction of your intention.

While living in the Tokyo region, I once went up and down the same flight of stairs three times without realizing it. Each time I went down the stairs to the platform, I boarded the train only to once again be headed in the wrong direction. When I returned to the original station, I apparently headed back up the stairs, got spun around, and came down to the same platform again.

Apparently an elder Japanese gentlemen had spotted the 6’1″ rather large white guy do this and after the third time, had enough mercy on me to politely tap me on the shoulder and take me across a pedestrian bridge to the staircase leading me to the other platform. To this day I think of  the amusement I provided him each time I showed back up at that platform with a more and more bewildered look and imagine him telling his buddies over sake about the big white guy who got confused.

So there you have it, a supposed travel pro who continues to make rookie mistakes. In the end, it’s all part of what makes travel fun.

What silly mistakes have you made when traveling?