When I started organizing culinary tours to Italy, I thought I knew what my role was.

I would plan beautiful itineraries, introduce travelers to places they might never find on their own, translate the language when necessary, explain Italian customs, and make sure everyone ate exceptionally well. Essentially, I would be sharing what I, and my dear collaborators, knew about Italy.

What I didn’t realize was how much my travelers would end up teaching me.

After years of traveling throughout Italy with hundreds of guests, I have collected far more than photographs, restaurant recommendations, and funny travel stories. I have collected lessons. Some are about travel, sure, but many are really about life.

With the theme of “back to school” this month, I wanted to share some lessons you have all taught me over the past ten years.

Never Lose Your Sense of Wonder

When you grow up in Italy, certain things become ordinary.

A medieval piazza? Normal. A church that’s 600 years old? There’s another one around the corner. Homemade pasta drying on a wooden board? That’s just lunch.

But then I watch someone see Tuscany for the first time. Or any part of Italy, really.

I see a traveler stop mid-sentence because the late-afternoon light has turned the hills golden, and they just have to snap a picture. I watch someone become emotional walking into a cathedral. I’ve seen grown adults absolutely mesmerized by a cheesemaker doing something his family has done for generations.

And I think, Oh yes. This really is incredible.

My guests have taught me not to become immune to beauty simply because I’ve seen it before. Not to take any of it for granted.

Sometimes familiarity makes us stop paying attention. Travel wakes us right back up.

Adventure Doesn’t Have an Age

Over the years, I’ve traveled with guests of many different ages, including plenty in their 70s and 80s.

And they have taught me something I hope I never forget: curiosity does not have an expiration date.

I’ve watched travelers climb into vans early in the morning, learn to make pasta from scratch, taste foods they’ve never tried, wander through villages they’ve never heard of, laugh with people whose language they don’t speak, and stay at the dinner table long after dessert has disappeared.

Some of my most adventurous guests haven’t necessarily been my youngest.

They are simply people who have decided they are still interested in the world.

And I find that incredibly inspiring.

Growing older doesn’t have to mean making your world smaller. If anything, perhaps it gives us permission to become more selective about what deserves our time—and more determined to actually do the things we’ve been postponing.

The Best Moments Are Often the Ones I Don’t Plan

I am a planner. It’s what I do. I think about logistics, transportation, timing, meals, reservations, walking distances, bathroom stops, weather, and approximately 847 other details that my guests will hopefully never have to think about.

But I hate to admit this, some of the best moments on my tours have nothing to do with what I planned.

It’s the conversation with a farmer that goes on longer than expected. It’s the shopkeeper who starts telling us about his grandmother. It’s an impromptu toast at lunch. It’s everyone laughing in the van about something that happened earlier that day. It’s sitting around a table after a cooking class when nobody seems particularly eager in leaving.

My travelers have taught me that you can create the conditions for a wonderful experience, but you cannot manufacture the magic.

You have to leave a little room for Italy to do its thing.

People Don’t Remember How Much They Saw. They Remember How They Felt.

This may be the biggest lesson of all.

When people first plan a trip to Italy, there is often an understandable temptation to see everything. Rome! Florence! Venice! Sicily! Amalfi! Cinque Terre!

And preferably all in seven days.

But after years of watching people travel, I’ve become more convinced than ever that more isn’t necessarily better.

My guests rarely go home talking about how many monuments they checked off a list. They talk about the lunch at the family-run winery. The woman who taught them how to shape pasta. The afternoon they spent wandering a small town. The farmer who proudly showed them his olive trees. The dinner where everyone laughed until their cheeks hurt.

That realization has influenced the way I design my tours. As many of you know, I prefer staying in one location—or at most two—rather than packing and unpacking every night. I want people to have time to settle in, recognize the person behind the hotel desk, discover their favorite café, and perhaps even start to feel like they belong there.

Because the goal isn’t simply to see Italy.

It’s to experience it.

Food Really Is a Universal Language

I have watched people who share almost no common language sit together at a table and somehow understand each other perfectly. A smile helps. So does the vino. But food does something remarkable.

Ask an Italian producer about their cheese, wine, olive oil, pasta, or family recipe, and suddenly language becomes secondary. Pride is easy to translate. So are the hand gestures!

I’ve watched my guests become fascinated by people who have dedicated their entire lives to making one thing exceptionally well. And I’ve watched the producers respond to that genuine interest.

There is something deeply human about sitting at another person’s table and eating what they have prepared for you. My clients have reminded me that food isn’t just something we consume while traveling. It is one of the most intimate ways we can understand a place, and its people.

Strangers Can Become Friends Remarkably Quickly

This is something I never fully anticipated when I began my business.

People often arrive on the first day knowing nobody except the person they traveled with—if they traveled with anyone at all. There are polite introductions. A little small talk. Everyone is figuring everyone else out. And then Italy gets involved.

A few shared meals, a cooking class, a missed turn, a wine tasting, and several hours in a van later, something changes.

People start saving seats for each other. Inside jokes develop. Phone numbers are exchanged. By the final dinner, the group sitting around the table often looks very different from the group that met on day one.

I’ve seen genuine friendships develop on my tours. I’ve had guests travel together again. I’ve watched people who were complete strangers a week earlier hug goodbye with tears in their eyes.

It has taught me how quickly human beings can connect when we step outside our normal routines and share something meaningful.

People Are Often Waiting for Permission to Enjoy Their Lives

This one has stayed with me.

Many of my travelers have spent decades working, raising families, caring for parents, building careers, managing households, and doing all the things responsible adults are supposed to do.

And then, finally, they book the trip. Sometimes they have dreamed about Italy for 20 or 30 years.

I have heard some version of “I’ve always wanted to do this” more times than I can count. And every time, I think: Why do we wait so long?

Of course, there are real responsibilities and financial considerations. Travel is a privilege, and I never forget that.

But my clients have taught me that there is also value in saying yes to yourself once in a while. So, take the trip. Order the dessert. Buy the beautiful ceramic bowl even though you have absolutely no idea how you’re getting it home! Stay at the table another hour.

Life cannot always be postponed until everything is perfectly convenient.

And Finally, They Have Taught Me Gratitude

I sometimes think about the fact that people entrust me with something incredibly valuable: not their travel resources, but their time.

They have saved money, coordinated schedules, crossed an ocean, and chosen to spend a week of their lives traveling with me.

I don’t take that lightly.

This business has brought people into my life whom I never would have met otherwise. Some have traveled with me once. Others have returned again and again, up to eight or nine times at this point! Many have stayed in touch long after their suitcases were unpacked.

They have celebrated birthdays, anniversaries, retirements, new chapters, and sometimes simply the fact that they finally decided to take the trip they had always dreamed about.

I may be the person who creates the itinerary and says, “Be downstairs at 9:00; the driver is waiting.” But my travelers have given me something in return.

They have reminded me to stay curious. To notice beauty. To slow down. To sit at the table longer. To keep meeting new people. To never assume I’ve seen everything there is to see.

And perhaps most importantly, they have reminded me that travel isn’t really about how far we go. It’s about how much we allow the experience to change us. After all these years, I still love introducing people to my Italy.

But I think one of the greatest surprises of this journey has been discovering just how much all of you have introduced me to as well.

And for that, I am incredibly grateful.