Touring Italy With Two Friends | How it all Went Wrong, What we Learned, and What We’ll Never Forget

Touring Italy with Two Friends for 5th Time in 7 Years | Motorcycle Memoir

I am writing this on a flight back to New York after spending six days riding motorcycles through Tuscany with two of my favorite people. We’ve ridden for a week in Italy five out of the past seven years—an annual tradition interrupted only by our weddings and the births of our children.

Since we first met in 2009, I’ve relocated to Southern California after a lifetime in New York. One friend now lives in Spain via London and raised in Italy, and the third in our trio resides in Hong Kong via London. It’s no small feat getting us all to travel to Italy once a year for a week of riding, laughing, and of course the roads and food!

Why do we do it? For the motorcycle riding, of course. But, I think after this year, it may actually be more for the friendship and the adventure. And this year was an adventure, let me tell you.

All of our trips have brought the typical thrills of riding, what many will agree, are some of the most beautiful and challenging roads in the world. Italy has it all—beautiful sweeping roads through hillsides, steep switchbacks, and small towns that look like they are out of a movie.

Dave Bober and Company on Italy Motorcycle TourMy personal favorites are the roads somewhere in between—roads that force me to use all my skills—the tight/technical roads with short straightaways interrupted by unpredictable radius turns at steep elevations. San Bernardino Pass, Valle Spluga, Apennine Mountains, Stelvio Pass…the list is endless. Ahhh, I want to turn the plane around and go back and do it all again!

Our annual pilgrimage to moto mecca also brings with it unpredictable obstacles and challenges that test our collective patience and will—bad weather bikes that don’t work properly, lost luggage, fatigue, no hotels available when we arrive to a new town, GPS malfunctions, and the occasional “off” (that to date has only left one of us with a bruised hip and ego). There are and will be things that happen on a multi-day motorcycle trip that break up the bliss that is riding in Italy.

Through it all, however, we have never lost our cool over the years and have always worked as a team to solve whatever challenge is in our path. In the end, the more challenging the obstacle, the better story it makes for over dinner and a bottle of wine.

That’s why I love these amigos—no one gets left behind and, when something unforeseen happens to one of us, it happens to all of us. There’s no blame—only support and a willingness to find a path that gets us back on track as a unit, together.

Each year, it seems one of us causes more of the adventure in our adventure than the others. Sadly, this year it was me, and the consequences were more than a simple inconvenience. But, the lessons learned from our struggles may last a lifetime, and how we reconciled it all was arguably our finest hour as riders and friends.

After day 1 of riding–all of us on Ducati Multistrada machinery–I was not happy with the bike’s suspension settings. So, I endeavored to make some adjustments on all the bikes that would help with the load we were carrying, as the grip that seemed unpredictable to all of us. A couple of clicks of rebound and compression damping adjustments, and some added spring-preload made a world of difference.

However, when I was trying to gauge how the rear shock was behaving on my friend’s bike after I made the changes, I mistakenly pushed down on the top box a few times, instead of the frame, to see how the shock compressed and rebounded. That would cost us dearly as it turns out.

Motorcycle Tour in Italy VillaThe next day that same top box fell off during a 60-mile or so leg of our daily ride. My friend did not feel it fall off and, compounding the loss, he had put all of his electronics, ID, passport, and other essential in the box, as rain was in the forecast. Odds are I damaged the mount on the top box and the rotten luck was that it did not fall off right then and there, or in a place we could recover it.

We retraced our 60-mile route no less than three times, but no top box was found. His phone was on airplane mode to avoid incuring roaming charges, so we could not find it by having it traced. In the end, it was all lost.

I felt horrible, of course, and offered to pay for his loss. Like the gentleman he is, he refused. So, before they had the chance to stop me, I paid for as many meals and hotel rooms for both of my friends during the rest of the trip.

My friend who lost all his valuables never yelled at me, and did not once say anything other than he knows I did not do it on purpose, that he forgives me, and that he does not want it to ruin my trip. It was so magnanimous, it almost brought me to tears.

After a hug and another apology from me, we all went into problem solving mode. His credit cards were cancelled, we filed a police report, and appointments were made for him to have travel documents so he could travel back to Hong Kong after the trip

Yes, there was more. On Day 4 of our six-day trip, we got caught on a mountain in a heavy downpour and stopped to quickly put on rain gear. In my haste to don the gear and put my soggy/wet/foggy glasses in my pocket, I must have dropped the key fob to the motorcycle and rode away.

Motorcycle Italy Tour helmetsSome motorcycles will start if the fob is close by (even in a puddle!) and continue to run without any warning as you and the bike distance yourself from the fob. When we got to the bottom of the mountain, I turned the bike off. Then, I tried to turn the bike back on and, of course, it would not start. Lost fob, and no key!

It rained the whole next day, so going back up and looking for the key on very technical, and now wet, road seemed an unnecessary risk—think needle in a haystack.

We had the rental company ship the back-up key to us in Florence, which was near where we were staying. Unfortunately, the key did not show up on time and, because Day 5 was a wash due to weather, that was effectively the end of my trip.

My two friends rode back to Rome on Day 6, where we stayed the night before returning to Spain, Hong Kong, and New York. I took a taxi from outside Florence to Rome, while the rental company picked up the bike.

In yet another display of true friendship and concern, and unbeknownst to me as I slept in that day before the taxi arrived to take me to Rome, my two friends in the wee early morning of Day 6 and before they set out on their long trip to Rome to end the trip decided to go up the mountain on their own and see if the fob was still there.

They felt bad my trip was cut short. Once again, I was moved by their commitment to our friendship and the selfless act of riding 30 miles up a wet mountain road to try and save me the money in key loss charges and shipping, and for me to continue the ride with them.

Ducati Multistrada tours in ItalyI sit here writing and thinking about how to wrap this up. I’m both moved by my friends’ generosity of spirit and moral compass, and equally upset at myself for the mistakes that I made. However, all that we had to go through would be a waste of time and money if there were no lessons to be learned here.

One of my friends who leads us on these annual trips is Italian, and knows the terrain and language. He said it best: “I learned that we should not only be responsible for our own organization and safety, but for each other’s as well. Let’s be mindful and accountable for not only our own belongings and preparedness, but also each other, because if something bad happens to one of us, it happens to all of us.” I love that.

The week was an invaluable lesson in humility, slowing down, being present in those moments that matter, and experiencing what true friends do for each other in times of crisis. It’s hard to articulate the bond we have and how it has gotten stronger—not from the thrill of a road, but from the unconditional support and unity we’ve exhibited for each other in trying times on the road over the years.

I know this particular trip will stay with me and be of help to me in many ways as I try to honor the loyalty of my friends by using what happened to make me a better friend, husband, and father. I also know my buddies will never let me live this one down, and I’m ok with that. And, yes, we’ll be riding again together next summer!

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