I’m sure that being a professional traveler looks good on the outside. I do my best to fit into cultures and present myself well on the road. But even the smoothest of cool cats make mistakes, and I’m hardly that cool. I’ve made an idiot of myself more than I even bother to keep track of.

Today I present a sort of confessional. A handful of times when I did something dumb enough to remember long term. As I write this, I realize I could keep going for days with similar stories, racked up over more than 25 years of travel. I share these awkward stories with you for one purpose, to help you remember that doing something stupid is just part of travel. I’ve gotten over it, and so will you.

Language is Hard

I will share a dirty secret with you- I am rubbish at foreign languages. School was so easy for me in every other respect, I got good grades without trying, but foreign language is what I suck at. Oh, the irony. It would have to be that I am the only person I know that actually needs to speak several foreign languages. Sigh.

Because of my perpetual battle with multiple foreign languages, I have many stories of misunderstandings and idiotic things I’ve said. I want you to know that if I can do it, so can you. Make an idiot of yourself, it’s ok. The locals appreciate the effort.

Years ago, when I was studying in Rome, I bought my fruit and veggies every day in the Campo dei Fiori. I had my regular places and felt very proud of myself for communicating my needs and understanding the responses. I happen to love peaches, and bought them almost every day. For months, I asked for “mezzo chilo di pesce” and the fruttivendolo always gave me a funny, sympathetic smile. One day I realized the word for peaches was pesche (pronounced PESS-kay) rather than pesce (PESH-ay), very similar words and only separated by a single letter. I’d been asking for months for a half kilo of fish, not peaches. D’oh.

Not as many years ago, I was working on book research, heading to the island of Capri. As I boarded the boat, I couldn’t help but notice the captain. He was muscular and tan, with an oily Julius Caesar haircut. He was like some sort of absurd Hollywood stereotype of a Roman God. He took my ticket and looked me up and down. A few minutes after departing, the hot captain came over and sat himself down next to me, handing me a beer and two plastic cups. Me? Hot guy wants to sit with me? Seriously?

And then he spoke….Italian is actually Florentine dialect. Italy is a relatively new country, and 100 years ago each region had its own unique language, sometimes indecipherable to other Italians. The dialects still persist in many parts of Italy, particularly in the south.

This is to explain that when the hot captain opened his mouth, out came a stream of deeply accented gibberish that made him sound like he had marbles in his mouth. I strained to listen and understand what he was saying. Nothing. Nada. I felt so stupid, I could not catch even a single word. He was obviously frustrated, and gestured at the beer. I split it between the two glasses and smiled apologetically.

I told him “mi dispiace, non ho capito…” and he tried again and again to talk to me. Still couldn’t understand Neapolitan. “Inglese?” I offered. Eventually we both sat in awkward silence and drank our beer. I think that silence lasted about 10 years, or that’s what it felt like. Exasperated , he gave up and went back to work and I sat through the rest of the ride turning several shades of red.

Tour Guides Make Mistakes Too, But Worse

Have you ever made a wrong turn? Yeah, no big deal, you just turn around and go back the other way. But what if 26 souls (who’ve paid good money for your expertise) are following behind you? I think I die inside a little when that happens.

Once I reserved a group dinner at a restaurant in Rome near Piazza Navona. I didn’t have their number on me, so I Googled it. They didn’t seem to remember me but booked me all the same. We, 29 of us, arrived at the restaurant and they had no reservation for me. How could that be possible? My group stood there staring at me as I quietly panicked. Ok, so I asked if there could possibly be another restaurant with a similar name nearby. “Bo.” said the host, an Italian way of saying “I dunno.” I planted my group at a picturesque fountain while I canvased the restaurants on Piazza Navona, and after checking four of them, my heart was racing and I was feeling desperate.

And then I saw one, and it had the exact same name as the restaurant I thought I’d reserved. Bingo! It was a tacky, touristy place, but they had chairs for us to sit in. They served something resembling Chef Boyardee pasta to eat and I was so embarrassed, but my group didn’t seem to mind since it had killer views of the fountains. Actually, I think they pretended to like it because they felt bad for me. Lesson learned, don’t trust Google.

On another occasion, when I reserved a group dinner the owner mentioned that he had another event at the restaurant that night. Was that ok? I didn’t mind. It was a big restaurant with multiple floors. Turned out, that other group was a tour from a competing company and they were seated literally inches from my group in a tight, underground room. When I say we were rubbing elbows, I mean that literally.

It was apparently their first night and the guide had a microphone, giving a noisy slideshow about their itinerary. It was our last night, where we normally say our goodbyes and give speeches, but in this case we couldn’t even hear ourselves think. The other tour guide came over to give me a piece of her mind in front of my group, how dare I eat at HER restaurant! I pointed out that I hadn’t planned the overlap and tried to say something funny to cut the tension.

She didn’t think I was funny, but once I mentioned who I worked for she immediately became more friendly and gave me her card…hoping for a job recommendation. Ummm. No. I don’t know who was more humiliated that night– me, the other tour guide, or the staff that had to deal with both of us.

One morning, after a night spent having a little too much fellowship with my tour guide colleagues, I sleepily led my group on the well worn path down into the Rome subway and the Vatican beyond. We boarded the subway, and as usual, I asked the group to split up into different cars so it was easier to get on.

Packed into train cars and chatting with the handful that stayed with me, something seemed off. The car wasn’t as full as it should have been. And then it dawned on me…we were going the wrong direction. Rather than panic, I searched for my group, counting them down as I went, and got them off the train. Did we have everyone? By some miracle, yes. We ran around to the other side of the tracks and got on a train going the right direction, arriving late for our reserved time slot. Luckily, Italians never really expect you to be on time, so the only damage was to my ego.

I did actually damage myself a few years back. Also in Rome. I was headed to San Clemente church, a marvelous sight that shows the layers of the city. Leading the group down the ramp to the entrance, I didn’t quite compute that the pine needles on the ramp, mixed with rain, mixed with Tom’s shoes’ crappy soles, made the most slick walking conditions you could create. I went down like a pratfall you see in the movies, comically tumbling and landing on my left leg with all of my weight. And like in the movies, the adrenaline and distilled humiliation I felt made me jump right back up without assessing the damage. I’m alright, I’m alright!

I hobbled down the steps with my local guide and asked her if she wouldn’t mind taking the group to the church without me while I went in search of ice. Once the group was out of sight, I assessed the damage. It was bad, but not broken. I knew it would become a hematoma, as my tour guiding skills also include amateur physician skills. I knew I wouldn’t be able to walk the rest of the day and I felt so dumb for all of it. So embarrassed to do that in front of my group.

And then something happened in the church. Another group stopped and gathered around someone, gasping and calling for help. Someone had suffered a heart attack. The church custodians rushed over and called the ambulance service, which arrived with sirens and lights ablaze. I sat on a pew lamenting my leg and watching the drama, the crew of medics swarming the church, not thinking about my group. They returned to the church just in time to see the hubbub, and every single one of them freaked out, thinking the person on the stretcher was me. Oh, great, the tour guide is dead. I noticed them and waved them over. My local guide was pale as a white sheet. While they were relieved when I got their attention, I think I was not the only person traumatized that day.

Sometimes, It’s Just Not Your Day

The queen of all days-gone-wrong was my day I had a misadventure in Tuscany. But car rentals are a deep well of embarrassing anecdotes.

Most recently, I was working on the Rick Steves Sicily book, navigating around parts of the island I didn’t know. I followed Google Maps to my hotel. Yeah, you know where this is going. The app lead me off the road and down to a city park. It told me to drive through the park and down a trail. That didn’t seem right, but the map offered no other solutions. The trail grew muddier, narrower, and more suspicious. Long canes of pampas grass rubbed alarmingly against either side of the car, so I stopped and got out.

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From there, I could actually see my hotel. It was on a hill perched above the park and there was no way this road was going there. So I had no choice. I had to drive in reverse to get out. The grass on either side of the car groaned and screeched as I carefully drove the narrow, curvy trail backwards. Sure enough, when I got out and look, a lovely long scratch ran the entire length of my dark green Fiat 500. Shitshitshit!

Rattled and upset about the car, I did finally get to my hotel. I set my phone and purse on top of the car, emptied the back and shut the hatch…hearing a sickening crunch as it slammed shut. That can’t be good. Had I damaged the car some other way? I inspected the door and my heart stopped when I found the culprit. It was my iPhone, smashed at the hinge between the hatch door and the car. It had slid down while I was unloading. Not only was the phone cracked, it had chipped the sunroof of the car. There are not enough expletives.

My phone is my office, I really can’t function properly without it. As it was, I couldn’t leave it in a shop to be fixed in Sicily, so I had to buy a new one, a $500 blunder. The finding of the phone shop and the day that went with it are another embarrassing tale for a different day. (Side note- I did have that phone fixed when I got home and a week later it fell out of my pocket while I was mowing the lawn…and I shredded it for good)

The day I had to return the car I felt like a cat with its tail between its legs. I was so worried and embarrassed, I’d never damaged a car before. I got to the Palermo airport and dutifully fessed up to my crimes. The attendant looked the car over and shrugged. You see, I’d bought the super extra insurance package. He joked that I could have crashed it if I’d wanted to. Thank goodness for being an overly cautious traveler, and thank goodness for the graciousness of Sicilians.

These are but a few of my embarrassing tales. I could go on. I hope they make you feel a little bit better about blunders you’ve made.

Want to join me in the confessional? Share your tales of woe and travel embarrassment here or on my Facebook page and I’ll compile them into an article of commiseration.