Why I Take My Son on Some of My Tours

Sometimes the most important lessons aren't taught at home or at school. They happen quietly, somewhere along the road.

We were waiting for one of the riders to catch up.

It was a warm summer afternoon in the Umbrian countryside, and the group had stopped at the top of a climb. Nobody was saying much. We were all looking down the road, waiting for the last cyclist to appear around the bend.

Then, from the child seat behind my bike, Leonardo broke the silence.

He looked at the empty road, smiled, and made a perfectly timed joke about our "late rider."

The whole group burst into laughter.

It wasn't rehearsed.

It wasn't something I had encouraged.

It was simply the kind of spontaneous humour that only children seem capable of.

I remember looking at him for a second and thinking that he had already understood something many adults spend a lifetime trying to learn: people rarely remember a perfect day, but they always remember how someone made them feel.

That afternoon, he wasn't just my son riding with us.

He had quietly become part of the group's story.

---

People often ask me why Leonardo occasionally joins me on some of my tours.

The answer is much simpler than they expect.

I don't bring him because I hope he'll become a tour guide one day.

I don't bring him because I want him to take over Greenways.

That choice will always belong to him.

I bring him because I want him to know, with complete honesty, what his father does for a living.

I want him to see what happens behind the scenes.

Not just that I leave home in the morning and come back in the evening.

Not just that work pays the bills or allows us to travel together.

I want him to understand where our life comes from.

The responsibility.

The preparation.

The long days.

The conversations.

The unexpected problems.

The trust people place in me when they choose to spend part of their journey with a stranger.

These are things no child can truly understand by simply being told.

They have to be witnessed.

When I was young, I knew my father worked hard.

But I never really knew what his days looked like.

I couldn't see the decisions he had to make.

The responsibilities he carried.

The people whose lives crossed his every day.

Looking back, I sometimes wish I had understood more.

Perhaps that is why I have chosen something different with Leonardo.

I want him to see my work not because I expect him to follow my path, but because I hope he grows up understanding that every meaningful life is built through commitment, responsibility, and relationships.

Not through shortcuts. Not through appearances. But one ordinary day at a time.

---

A tour, after all, is never just about the places we visit.

It's about the people who share the journey.

And that's exactly what I hope Leonardo remembers.

Not the kilometers we ride.

Not the villages we stop in.

Not even the vineyards or the views.

I hope he remembers the conversations.

The laughter.

The generosity of people who, only a few hours earlier, had never met each other.

Because that's where Greenways truly begins. Not on a bicycle. But between people

---

Leonardo has a way of making people forget they met only a few hours earlier.

It happens almost every time.

Someone asks his name.

Then his age.

A few words in English.

A smile.

A high five.

And before long, the conversation somehow belongs to him too.

I remember one tour with Carly, Destiny and Carly's mother.

From the very beginning, there was something completely natural about the way they connected.

Leonardo kept turning around from the child seat to wave at them.

Now and then he stretched out his little hand towards me, asking for a high five while we were riding.

We laughed.

They laughed.

The kilometres passed almost unnoticed.

There was no effort to entertain anyone.

No one was trying too hard.

It was simply one of those rare days when everything felt easy.

By lunchtime, it no longer felt as though they were guests.

It felt as though we had known each other for much longer. When the tour came to an end, something happened that stayed with me. Leonardo didn't want to say goodbye. He was in Carly and Destiny's arms, smiling, laughing, and holding on for just a little longer before leaving.

Watching that moment, I realised something.

He wasn't quietly observing the experience from the child seat. He had become part of it.

Watching him reminded me of something adults often forget.

They don't worry about where someone comes from.

They don't wonder what language they speak.

They don't think about age, culture, or differences.

They simply decide whether someone feels kind.

And if they do, the rest takes care of itself.

Sometimes I wonder if adults spend too much time learning things that children seem to understand instinctively.

That trust begins with curiosity.

That friendship often starts with something as simple as a smile.

And that making people feel welcome doesn't require a script.

Only genuine attention.

I often say that Greenways isn't just about showing people beautiful places.

It's about creating the space for real human connections to happen.

Leo has reminded me of that more than once.

Without ever knowing he was teaching me anything.

---

There is another moment that often comes back to my mind.

It never happened on a bike.

It happened around a table.

One afternoon, during lunch at a small family winery, Leonardo picked up a glass of wine. Without anyone saying a word, he held it by the stem, gently swirled it, brought it to his nose, and took a deep breath.

Then he smiled.

"Ahhh..."

The same spontaneous sound someone makes when smelling fresh bread, clean laundry, or the aroma of something they love.

Everyone at the table laughed.

Not because he was pretending to be an adult.

But because we all realised exactly what had happened.

Nobody had taught him how to do that.

He had simply been watching.

Watching me.

Watching our guests.

Watching the winemakers who, with quiet pride, pour the result of an entire year's work into a single glass.

Children don't always learn from what we teach. More often, they learn from what we repeatedly do.

That moment reminded me that our actions will always speak louder than our words.

It made me wonder how many of the habits we pass on to our children go unnoticed by us.

Not because we planned them.

But simply because they were paying attention.

At the end of every tour, once the last goodbye has been said, we load the bikes back into the van and begin the drive home.

Those quiet moments are often my favourite part of the day.

Sometimes we sing along to the same songs that had been playing through the speaker while we were riding.

Sometimes we talk.

About the people we met.

The funny conversations.

The lunch.

The dog that ran alongside us for a few hundred metres.

Or the guest who couldn't stop smiling after the first sip of Sagrantino.

Now and then, while I'm driving, I feel a small hand reaching towards me.

Leonardo is asking for one last high five before he falls asleep.

It's become our little ritual.

One simple gesture.

No words.

Just a reminder that we shared another day.

Years from now, I don't expect him to remember every road we've ridden.

He probably won't remember every village, every winery, or every beautiful view across the Umbrian hills.

And that's perfectly fine.

I hope he remembers something far more important.

I hope he remembers that his father loved what he did.

That work was never just about earning a living.

It was about welcoming people.

Listening to their stories.

Sharing time around a table.

Building trust.

Creating memories.

Most of all, I hope he remembers that there was never a difference between the person I was at work and the person I was at home.

Because Greenways has never been a character I step into every morning.

It has always been an extension of the way I choose to live.

One day, Leonardo will choose his own path.

It may have nothing to do with bicycles.

Or travel.

Or Greenways.

And if that is what makes him happy, I will be proud of him.

Because the point was never to pass on a business.

It was to pass on a way of looking at the world.

A way of treating people.

A way of paying attention.

A way of finding joy in simple things.

One day, he will probably forget many of the roads we've ridden together.

I only hope he never forgets the people we met along the way.

Because, in the end...

that has always been what Greenways is really about. If this story resonated with you, you may also enjoy: The Art of Slowing Down