Top 25 Italy Moments – #13 Why I Was a Lousy Tour Guide

Me as a guide in 2006 "Photo by BJ Stanbery"

In 2006 I became a cycling guide in Italy. I wasn’t much of a cyclist and at the same time I was certain my passion for Italy and knowledge would be more than enough to lead clients through the region and give them a great experience.

After all, I basically served in this role in 1995 on my University campus and again in 2002 leading two friends on two occasions through Rome and Tuscany. I passed the Italian language test in order to work in Italy and so I assumed my language was at least “good enough”.

I quickly realized my language was not nearly enough and on my first week off in Italy I went to language school. I loved being in school and staying in the stunning Sicilian town of Taormina. I loved being there so much I really hated that I had to actually go to work the following week. I was fortunate enough to be able to shadow my first trip in Sicily and watch 2 professional and talented guides do a job I knew, even at the time, I would not be able to do.

Within the first few days of my guiding it was apparent to me that I lacked a very particular skill for being a guide in a foreign country: nurturing. My colleagues, mostly female, were so naturally adept at putting the client first, even to the guides’ obvious discomfort and frustration. I was amazed by the energy and stamina these women possessed, and I knew I was in trouble.

Why? Because I was in Italy! Italy was my place, my home for discovery, my soul-seeking enterprise and no client, no boss, and certainly no language barrier was going to get in the way of MY journey. I was in Italy, someone was paying me (very sparsely) to be there and I would be damned if anything was going to hinder my pilgrimage of self discovery. Of course this is hindsight. At the time I was a nervous wreck. Was I saying the right things, would I be on time? My head hurt so badly from dehydration, I was so tired, so tense, and without experience to show me when it would ease.

The very talented guides I worked with seemed to have limitless energy and almost a macho need to test their mental and physical capacities. If two talented guides worked side by side for the first time it was easy to see that they naturally competed to see who was the bigger martyr. Sacrifice was indeed the game, and I had no compunction to join nor any concept of the rules. From who swept the floor the most to who took out more trash, loaded more bikes, cleaned more dishes, read and wrote more notes; this was about the JOB.

Now, please know that I respect these talented folks enormously and this was the first job in my life where I faced the stark reality that on my best day I would NEVER and I mean that, be as good as most of these talented people. The problem was: I didn’t want to be. I wanted something else. I wanted a menial job so that I could be there and learning, experiencing Italy. I simply needed to survive and for the first time in my life I did not feel the burn to excel.

Sure, I gave a few wine seminars while I was there and I cooked some outstanding food for the group. I loved doing these things because it was the only time in my whole experience that my colleagues saw that I was more than a useless sack. I was so slow at loading bikes, terrible with knots, nearly sub-human with verbal directions (always have been), and not even proficient with the language. I was working uphill all the time and so when clients needed me, I was not 100% present.

I remain guilty to this day and damned near regretful about my intolerance of clients. Yet, I should be grateful. Because it was the client that showed me I was not in the right place. I was most definitely in the right country, just at the wrong time doing the wrong thing.

This was most clear one bright morning in the Maremma district of Tuscany. There were always 2 guides on a bike trip. One guide would cycle while the other would drive the support van. On this particular day I was the cyclist; my favorite job in the world because I had 1 clear task, to manage the riders and chat with them.

We had taken a short break mid-morning after riding through the tufa rock town of Sovana. Some of the faster riders had gone out ahead and now I was about to join the main group of riders for the remainder of the journey. I was already very tired as the hills were intense and steep in this region and I had been forced to double back on a couple of occasions to encourage timid riders to get down the hills. As we all were exiting an excellent coffee shop in town I heard a guest say loudly to another guest “my God I really miss my Starbucks!” I was devastated. You can miss cheeseburgers, fast flushing toilets, self-serve gas, and drive thru food while you are in Italy. You are allowed to miss wide roads, big parking lots, and reality TV if you are inclined. However, when you are in Italy, you cannot be forlorn for motherfucking Starbucks. You are in the land of coffee pressed through the clouds of heaven and laid in your cup by Maestros descended from the Renaissance. I could only think to say vaffanculo! So I knew I had to go.

I told the group that I was going to go out ahead and catch the lead riders and I would meet them in a few at the next town. I waved goodbye as I put my map in my pocket and went down the nearest road that would lead me as far from anyone in the group as possible. I rode alone for 1 and a half hours in the beautiful iron-rich hills of the Maremma. I thought about my future and my past. I knew this was not what I wanted to do. I had just left a very interesting job as a wine cellar manager and consultant to come here. I had broken up with a girl to come to Italy and finally live my life here. Yet, that was not the expectation of the company where I toiled. They had no interest in my romantic notions or my arguments to let me create wine-based trips in Italy. I knew I was in the wrong place and so did the company.

At the end of that trip I was told of my very discouraging client ratings regarding my performance. I was not shocked, and at the same time I was crushed. I had just spent the previous 10 years of my life making customers happy with my work. I had made life-long friendships with many of my clients and so the idea of being disliked and in some cases, despised, was more than I could handle.

The company offered me another chance (albeit one set on a collision course with failure) to right the ship. Instead, I informed them I had seen the writing on the wall and asked would it be possible to help in another way as I was not going to succeed as a guide? The company seemed surprised and at the same time obliged and sent me on a great trek across France and Ireland to deliver a van and bikes. It was my greatest 10 days on that trip to Europe. Sadly at the end my money was stolen (see the story here) on my return from Ireland to Italy. I left Europe in 2006 with my tail between my legs. I was a beaten man who had failed miserably at something where I thought I would excel.

I knew I had done a poor job and it would take me several years and even another attempt in the travel business to know why. I am now on a path the resembles very much my lone ride through the hills of Tuscany. I am free to see what I see and to tell of its greatness and wonder. Working for the company in Italy taught me much more about who I am not, as it appears I already knew who I was.


  1. says

    Good day, M! I loved reading this. It's amazing how many signs we can see in hindsight about our true inner selves. Thank you for sharing!

    Question: you mention a job as a wine cellar manager. Do you remember us meeting years back, our first meeting since UD days, at the Inwood shopping center? I don't recall the name of the wine shop (though we loved it), but is that the place you mentioned? Do you remember us bumping into one another? It was in the parking lot near the Inwood theater. I think the Bookstop was still open, but am not positive.

    I'm glad that day crossed our paths. :)

  2. says

    Very interesting story, an well written! :)
    Love: "However, when you are in Italy, you cannot be forlorn for motherfucking Starbucks. You are in the land of coffee pressed through the clouds of heaven and laid in your cup by Maestros descended from the Renaissance." 😉

  3. says

    Loved this! Very well written. I just completed a 2 week school to become a Tour Director to take people on trips, but have also been wondering if it's really for me. I haven't done it yet. Anyway, thanks for the insight. So, what are you doing now?

    • says

      Travel Spirit why dont you email me directly at and I would be happy to chat with you about this. I went on to establish one of the most exciting and successful tour companies in Southern Italy so my greater insight stems from all aspects of the biz. I would be pleased to offer some advice :-)

  4. says

    Great piece Mike. This is overflowing with rich and honest life experience and I certainly can relate. At least you were afforded this window into yourself in a marvelous and beautiful setting. I think that setbacks are nothing more than opportunities, but it is hard to know that when they are happening.
    Now I'm looking forward to reading about about how your money was stolen, and please know that it is my plan to find whoever did that to you and lay a little east coast justice on them, if you know what I mean. When next you see them, they will be limping, with one gonad left.

    • says

      I think you may be taking it out of context, as this particular behavior certainly was not universally the case. I think the overall gist of my post paints an honestly flattering image of the successful guides and a rather failing view of myself. I am confident I do not come off as a hero here. In addition, the observation for which you comment was simply my way of explaining a way of doing things that while wholly matriarchal and nurturing in their essence, there was indeed a bit of a pissing contest element to the day to day chest beating for who could out work whom in the matriarchal capacity. It was actually a little ironic to see the naturally dismissive spirit to male horn-blowing be perhaps a bit out paced by the parties involved to exact precision and duty to the endeavors of leading, cleaning, not complaining, and enduring. It was an environment that made the company very successful and in many ways made guest experiences world-class. However, if you look at the Philosophical principle of The Other that I am loosely invoking in my post, you will see that I am attempting to say with a bit of humor that I was The Other in a society that functioned well as The Same. I was the odd man out in a place that must have order and adherence to certain successful principles in order to succeed. In this, much like being in a den of Gladiators training and prepping for combat I was not possessed with the skills nor the mental toughness to succeed in the role. Once again, I failed at something because I lacked the talent and quite possibly the desire to do a job that was needed in the way it was needed.
      I take sole responsibility for my lack of fortitude and inertia to be successful. Macho and unforgiving while not pertaining to all certainly was and continues to be the way in which I saw the profession at its height. Those who succeeded by other means notwithstanding.
      I hope this sheds some light on my commentary and please accept my apologies if I offended your sensibilities in any way.

      • says

        to elaborate one step further: by unforgiving I mean to say that methods to success can often be off the path prescribed. The gladiators here accepted only those that followed the track and the chain. Ways to success not along these lines were dismissed and derided. This is by its nature a little unforgiving but maybe the more apt term would have been intolerant. Once again this generality most certainly did not apply to all, yet it certainly applies.

      • Ashley says

        I was not at all offended…no worries. I found it really interesting to read your perception of this years later.

        • says

          In all honesty you were an exception and of all the people I would not want to offend it would be you. You were a patient exception with a natural curiosity as well as a keen understanding of the job that bordered on fine art. As I said this was my perception and I wanted this to point much more to my own failings and shortcomings versus pointing to my perceived flaws in the system.

  5. Ashley says

    Hmm…I might argue with your last comments however. Although I agree with you that there were certainly methods that became habit and many things that had been set in stone as best practices, so to speak, I would argue that many aspects of the job were ever-evolving and open to new eyes. In some cases however, it was almost necessary to rely on certain tried and true functionalities so as to leave brain space for the inevitable chaos invoked by the addition of inclement weather, untenable guests and italian traffic.

    • says

      You are 100% correct here. I am not saying the regimen was wrong I am saying that variation from it and especially in the living environment of leaders vs guest experiences was frowned upon. In essence I should be more thorough with this kind of post yet have no interest in a detailed exposé of something that in essence works very well.
      My failings at this have haunted me for a very long time and expunging some of the self-frustration was my impetus to write. The society of leaders was a warm and inviting place for many. It was challenging and difficult for me to
      Imagine I did not fit. I have grown to understand the reasons in recent years and this is why I am out on this path now.
      Believe me when I say that the lessons I learned from you are only exceeded by my admiration of you as a person and a leader. You have crazy talent and I remain in awe of your work and a few others. I never took the time to adequately explain how much I gathered from you nor how disappointed I was in myself for not achieving a level of success you would have liked from me. You did the job with mastery and aplomb. So much so I knew I was out of my league. This was tough for me to swallow, but true.
      Ashley thanks for taking the time to respond and bigger thanks for reading my work of which I am now very proud.
      Best to you and your lovely family!

  6. says

    What a great piece, Michael. I was getting winded, frustrated, sweating, blisters on my heels, and downright desperate to escape as I read this. Adventurers do not fit in the same box with people who need Starbucks in an Italian village… You are not a joiner. Neither am I. Give me five minutes with those clients and I'm outta' there! I love it.

    • says

      I had a very bright client from Seattle tell me this almost word for word on my shadow trip. He told me that I was an excellent actor because I was obviously an introvert who fooled the world to believing the opposite (all but him obviously)
      I want to share my Italy in so many ways. Clearly not the way this job required. George this comment made my day. I still anguish over my performance in this job and am only now willing to share my feelings and frustrations.

  7. says

    My wise old grandmother taught me that what I do will determine what 80% of the people think of me, 10% will not like what I do under any circumstances, and 10% will like what I do regardless of what it is. That was 45 years ago. Still holds true.

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