After years of taking travelers around Italy, I have a few confessions to make.

When I started Lazy Italian Culinary Adventures, I knew I wanted to show people a different side of Italy. I wanted smaller groups, locally owned businesses, long meals, family-run farms, cooking classes, authentic small wineries, little towns, and experiences that felt personal rather than “packaged.”

What I didn’t know was how much I would learn about people along the way—or how predictable some things would become.

So, since we’re among friends, I thought it was time to confess a few things.

Confession #1: I still worry before every tour.

You might think that after doing this for years, I simply arrive, grab our itinerary, and off we go.

Not exactly.

Before every tour, I worry. I check reservations. I check transportation. I check the weather. I check things I’ve already checked three times. I wonder whether everyone will like the activities, whether the restaurant I love will live up to my praise, whether the weather will cooperate, and whether everyone in the group will get along.

Then the tour begins, everyone settles in, the wine starts flowing, and I remember why I do this.

But yes, I still worry. Every. Single. Time.

Confession #2: I can usually tell when you’ve finally relaxed.

It doesn’t always happen on the first day. In fact, it rarely does.

At the beginning of a trip, people want to know what’s next. What time are we leaving tomorrow? How long is the drive? What should I wear? What time is dinner? Where are we going after lunch?

And then, usually somewhere around day two or three, something changes.

People stop asking quite so many questions. They settle into the rhythm. They realize I’ve got them. They start showing up in the lobby ready for the day without necessarily needing to know every little detail about what comes next.

I love that moment because that’s when their vacation really begins.

Confession #3: I love when lunch takes too long.

There is a schedule, of course. I spend months working on it.

And then Italy happens.

Lunch that was supposed to last 90 minutes turns into two hours. Someone brings another bottle of wine. The owner comes over to talk to us. Dessert appears. Then comes coffee. Then perhaps a little limoncello, amaro, or grappa.

Suddenly we’re running behind.

And unless we’re missing something important, I secretly love it.

Because nobody comes home from Italy talking about the day everything ran precisely on schedule. They talk about that lunch that seemed to go on forever. Or until the driver finally calls me to get a move on it!

Confession #4: I know you’re going to buy too much stuff.

Before the trip, I tell everyone to leave room in their suitcase.

Some of you listen.

Most of you do not.

Then we encounter ceramics, olive oil, wine, linens, leather goods, pasta, cookies, cheese, kitchen utensils, and that one absolutely essential decorative item that nobody knew existed until 20 minutes ago.

By the end of the week, someone is inevitably sitting on a suitcase trying to close it.

I have seen this movie before.

I know how it ends. Usually with an overweight luggage fee at the airport.

Confession #5: I pay attention to what you eat.

Not in a creepy way, I promise.

But I notice.

I notice when someone who told me they weren’t much of a wine drinker asks where they can buy a bottle of the wine we just tasted. I notice when someone who says that they don’t normally eat breakfast discovers Italian cornetti. I notice when a traveler takes the first bite and gets very quiet. I notice when the lips pucker because the extra virgin olive oil is just so peppery perfect.

And I especially notice when someone says, “I’m really not that hungry,” and then proceeds to enjoy a full meal. With dessert!

Italy has a way of doing that to people. And I love every minute of every bite that you enjoy.

Confession #6: Some of my favorite places aren’t impressive at first glance.

I’ve taken travelers to places where I suspect their first thought was, “This is it?”

There may be no grand entrance. No fancy tasting room. No perfectly staged gift shop. Sometimes it’s simply a farm, a kitchen, a cellar, or a family business that has been doing the same thing for generations.

And then we meet the people.

Someone starts telling us about the land. Someone shows us how the cheese is made. Someone brings out something they’ve been preparing since early that morning. We sit down at a table, and suddenly that unassuming place becomes one of everyone’s favorite experiences of the week.

Those are the places I treasure most.

Confession #7: I love watching the group become “a group.”

This is one of the best parts of my job.

On the first day, everyone is polite. People introduce themselves. They make small talk. They sit with the person they came with.

A few days later, everyone’s moving around the table. Someone is saving a seat for someone they didn’t know three days ago. People are exchanging phone numbers and pictures. There are inside jokes no one remembers starting.

By the end of the week, I sometimes have to remind myself that many of these people were complete strangers when they arrived.

I’ve watched real friendships begin on these trips, and I don’t think I’ll ever get tired of seeing it.

Confession #8: I sometimes know you’re going to love something before you do.

There are moments when I wish I could watch an experience through the eyes of someone seeing it for the first time.

I know what’s waiting behind the door. You don’t.

I know how beautiful the view is going to be when we come around the corner. I know how good that pasta is. I know the charm of the person we’re about to meet. I know you’re probably going to want to take that olive oil home. Perhaps even the producer!

Sometimes I find myself watching my travelers instead of watching what’s happening.

Seeing someone experience something I already love makes me love it all over again.

Confession #9: Not everything goes according to plan.

There. I said it.

Italy is wonderful. Italy is also Italy. And if you know, you know!

Traffic happens. Weather happens. Someone gets delayed. A restaurant changes something. A road closes. A producer needs to adjust our visit. Things occasionally move at a pace that would send the average American into cardiac arrest.

Part of my job is making sure you don’t have to worry about most of that.

Sometimes I’m solving a problem while you’re enjoying your aperitivo and you never even know there was a problem. That’s exactly how I like it.

And when something can’t be fixed? We adapt. Some of the funniest travel stories start with something that wasn’t supposed to happen.

Confession #10: Saying goodbye is harder than I expected.

At the beginning of the week, I have a group of travelers.

By the end, we’ve eaten together, traveled together, laughed together, probably gotten a little lost together, and shared experiences that are difficult to explain to anyone who wasn’t there.

Then suddenly it’s “the last supper.“

Someone inevitably says, “How is it already over?”

And I wonder the same thing.

There are hugs. There are promises to keep in touch. There are discussions about where we should go together next. And the following morning, everyone starts heading home.

The quiet afterward always feels a little strange.

And One Final Confession…

I didn’t expect this business to become as personal as it has.

I thought I was creating culinary tours. And technically, I suppose I am.

But somewhere along the way, it became about much more than food and travel.

It’s about introducing people to an Italy that means something to me. It’s about supporting families and small businesses I’m proud to work with. It’s about watching someone taste something they’ve never tasted before, see a place they’ve dreamed about for years, or discover a town they didn’t even know existed.

It’s about sitting around a table in Italy with people who were strangers a few days earlier and realizing nobody is in a hurry to leave.

And perhaps that’s my biggest confession of all.

After all these years, after all the planning, logistics, early mornings, schedule changes, phone calls, reservations, and occasional Italian chaos, I still get excited about the next trip.

I still love wondering who will be sitting around the table.

I still love watching Italy work its magic on someone new.

And I still believe one of the very best ways to experience this country is slowly, around a table, with good food and good people.

Although I do have one request: Please leave some room in your suitcase next time!

But I already know how this is going to end.