Sometimes things do not go as planned. The joy of travel for me is exploring the unknown, getting a little out of my comfort zone to learn more about a place or culture. This sense of adventure can lead to unfortunate situations and can create bouts of utter frustration or anger. Luckily, time heals all wounds, supposedly, and these “misadventures” become an anecdote to share with others. I have decided to share a few of mine, starting with my first true international misadventure.

Back in 2005, my brother Brad and I planned a brothers’ trip through Italy, starting in Florence, cruising through Cinque Terre and ending at the White Truffle Festival in Piedmont, which was as awesome as it sounds. Brad was already in Italy, having attended a friend’s wedding in Tuscany the previous week and we planned to meet up at our hotel in Florence. I was literally flying solo and arrived in Rome, with a plan to take the train to Florence.

I tend to be a meticulous researcher in general, and I had done my due diligence in preparing for my journey. I had found the easiest transfer from the airport to Rome Central train station, the cost and frequency, as well as the various train times for my connecting train to Florence, just in case my flights were delayed. I knew where to purchase tickets, how to walk to the hotel in Florence and the contact information for the hotel if I needed to leave Brad a message. I had the details covered, or so I thought. One massive oversight was the need to validate my train ticket and this led to an awkward situation within thirty minutes of first stepping foot into Europe.

I purchased the ticket for the train from the airport to Rome, on the fantastically named Leonardo Express. I went to the board the train and noticed yellow boxes at the beginning of the platform. I observed about half the passengers sticking their tickets into these mysterious yellow boxes. I attempted the same, and found nothing happened. I saw multiple people walk past me without even glancing at the boxes, so I said “screw it” and boarded the train. That was a mistake.

As we left the station for the short ride to Rome, the conductor came around and checked for tickets. I handed over my ticket and instantly knew by the man’s facial expression that something was amiss. What came next was a flurry of unintelligible Italian and exaggerated hand gestures. I attempted to communicate, saying “Inglese?” This was not meet with much appreciation. All the passengers around me began staring at me and I knew I had done something stupid. He continued yelling for what seemed like an hour before the woman sitting across from me began to laugh. She leaned over and said “you did not validate your ticket. The conductor wants to fine you and wants whatever cash you have in your wallet.”

Shit.

To explain the validating process, and what I should have done, train tickets sold in Italy do not have a date or time printed on them. In order to use the ticket, you validate the ticket on the platform by inserting them into a slot in a yellow box, which stamps the date and time across the bottom of the ticket. This shows the conductor that you are not reusing an old ticket and have just recently stamped your ticket. In my situation, the box I used was not working, which in hindsight should not have been surprising since this was the Italian train system.

I had my new friend explain to the man that I did not know I had to validate my ticket and that I did not have any cash, which was truthful. She explained this to the conductor, who was becoming more and more upset with my general existence.

The kind woman said that the man wanted to follow me to an ATM when we arrived at the Rome station so I could pay him in cash. He wanted at least €40. Alarms starting going off in my head. Even though this was my first time overseas, I knew that the prospect of a stranger following me to an ATM was not in my best interest. In fact, it sounded like straight robbery. My journey was officially off to a rough start.

Luckily, the woman translating was in my corner. She apologised for the conductor, whom she acknowledged was just trying to rip me off because I was a tourist and had made a simple mistake. There was a legitimate fine for not validating tickets, but this conductor was clearly just interested in collecting whatever extra cash he could. I tried to explain to the man that I had attempted to use the yellow box but that nothing happened. That story was of no interest to him. He eventually moved on, checking the rest of the tickets in the carriage. Once he was out of sight, the woman provided me with sound advice: “When we arrive at Rome, just run.” I evaluated my options. Wait for the conductor to follow me to an ATM, where he would most likely rob me of whatever I could take out in one transaction, or just make a run for it. I choose the latter.

As the train screeched into Rome, I grabbed my luggage, waited at the doors. As soon as they opened, I bolted. I heard the conductor blowing a whistle and yelling in my direction. I glanced back briefly to see him trotting towards me. I weaved through the crowd on the platform like a running back, bumping a few passengers with my bag along the way, but not making too big of a scene. I emerged in the ticketing hall and found an open window, where I quickly purchased a ticket to Florence. I dashed to the platform and boarded the train, minutes before it departed the station. Even in my haste, I was able to to validate the ticket this time around.

I learned quickly from this experience, and made sure to validate my ticket for every train ride, despite the fact that most of the yellow boxes were not operational. I made it safely and without incident to Florence, where I had an unbelievable week. At the time, I was confused and slightly flustered, though the “run” advice worked quite well. But hey, that is what makes misadventures interesting. Eventually.