You’ve booked the flights. You’ve chosen the hotels. You’ve made the restaurant reservations. You’ve bought comfortable shoes. You’ve checked the weather fourteen times. You’ve watched approximately 437 Instagram reels about Italy.

You’re ready.

And then Italy happens.

The train is delayed. The restaurant you’ve been dreaming about is inexplicably closed. It rains on the exact day you booked a boat. Your rental car is roughly the size of your carry-on. Google Maps sends you down a street that appears to have been designed for a donkey in 1472.

Welcome to Italy.

After years of bringing travelers here—and now spending a good portion of my own life here—I’ve learned something important: a few things are probably going to go wrong on your trip to Italy.

And that’s perfectly fine.

In fact, I think one of the best things you can pack for Italy is something that won’t take up any room in your suitcase: flexibility. Because Italy is wonderful. Italy is beautiful. Italy can be magical.

Italy is not always efficient. And sometimes, that’s part of the charm.

Your Train Might Be Late

Italy has a wonderful train system, and I recommend it all the time. But trains get delayed. Strikes happen. Connections get missed.

This is why I cringe a little when I see itineraries planned down to the minute. Arrive in Florence at 10:42. Museum reservation at 11:15. Lunch at 1:30. Train to Rome at 2:17. Dinner reservation at 7:35.

Please don’t do this to yourself. Build some breathing room into your trip. And if your train is delayed? Get a coffee. Buy a snack. People-watch. You’ll get there.

Unless you’re trying to catch a flight. Then you have my permission to panic a little.

The Restaurant Might Be Closed

This is one of my favorites.

Google says it’s open. The website says it’s open. The little sign hanging on the door may even suggest that it should be open.

But it is not open. Why? Who knows. Perhaps there’s a family event. Perhaps they’re on vacation. Perhaps the owner decided that Tuesday seemed like a lovely day to go fishing.

Whatever the reason, you’re standing outside staring at a locked door.

This is why I always tell people not to become so attached to one particular restaurant that eating there becomes a requirement for having a good trip.

Have places you want to try, absolutely. Make reservations for special meals.

But occasionally, let Italy feed you wherever you happen to be. Some of the best meals I’ve had weren’t planned at all. I mean, have you ever had lunch at an Autogrill on the side of the highway? One word: Amazing!

It Might Rain

You spent thousands of dollars to come to Italy, and apparently nobody informed Mother Nature.

It happens. It happens on my tours too. Sorry to say.

So your beautiful day in Tuscany might be cloudy. Your boat ride might get canceled. You might arrive in Positano expecting the photographs you’ve seen online and instead find yourself buying an umbrella.

Don’t let the weather become the trip. Have a long lunch. Visit a museum. Sit in a café. Order another cappuccino. And yes, I know the Italians aren’t ordering one at 3:00 in the afternoon. They’ll survive the scandal.

One rainy afternoon doesn’t ruin Italy. Sometimes it gives you permission to slow down.

You Are Probably Going to Get Lost

Especially if you’re driving.

There are streets in Italy that I am convinced were created specifically to test relationships.

“Turn right.” “THIS CAN’T POSSIBLY BE A ROAD.” “Google says turn right.” “There is an 87-year-old woman walking down it carrying groceries!” “It’s the wrong road!”

Good luck.

Historic centers, restricted traffic zones, one-way streets and medieval roads can make driving interesting, to put it mildly.

Even walking, you will occasionally take the wrong turn.

But here’s the thing about getting lost in Italy: sometimes the wrong turn is better than the right one. You find a bakery. A little church. A piazza you didn’t know existed. A shop selling something you absolutely do not need but somehow end up bringing home.

Obviously, use common sense and don’t wander somewhere unsafe. But don’t be afraid of getting a little lost. Italy is particularly good at rewarding wandering.

Not Every Meal Will Be the Best Meal of Your Life

I’m probably not supposed to say this as someone who runs culinary tours, but it’s true.

You can have a mediocre meal in Italy.

There. I said it.

Not every plate of pasta was handmade that morning by someone’s nonna. Not every restaurant is wonderful. Tourist traps exist here just like they exist everywhere else. Especially the ones near the major attractions with white and red checkered tablecloths.

And sometimes the restaurant with thousands of glowing reviews will disappoint you while the little place you wandered into because you were hungry will serve you something you’ll talk about for years to come.

Food is part of the adventure. Especially on my trips. But one disappointing plate of pasta does not constitute an Italian emergency.

Plus, there’s always the next meal.

Things Will Take Longer Than You Think

This may be the hardest adjustment for Americans. We are used to efficiency. We want to sit down, order, eat, pay and move on to the next thing. But Italy has other plans.

Lunch can take two hours. Dinner can take three. The check may not arrive until you ask for it.

Someone working behind a counter may finish an entire conversation with another customer before acknowledging that you are standing there.

At first, this can feel frustrating. Eventually, if you let it, something changes. You stop looking at your watch. You realize there’s nowhere you urgently need to be. You order another coffee. You finish the conversation.

And perhaps you begin to understand why Italians aren’t always in such a hurry.

Something You Really Wanted to Do Might Not Happen

This is the big one.

The boat gets canceled because the sea is rough. The winery has to change your appointment. The attraction you wanted to visit is closed. The chef gets sick. The weather changes. Plans have to change.

This can be especially disappointing when you’ve traveled thousands of miles and perhaps dreamed about this trip for years.

Be disappointed for a minute. Then ask one question: What are we doing instead? Because “instead” has produced some pretty wonderful travel memories.

Instead might be a three-hour lunch. Instead might be a little town you hadn’t planned to visit. Instead might be sitting under an awning drinking wine while a thunderstorm rolls through Tuscany. Instead might end up being the story you tell when someone asks what you loved most about Italy.

And Please Don’t Try to Control Every Minute

Plan your trip, of course.

Book your important museums. Reserve restaurants you really want to visit. Buy your train tickets. Research your hotels. Know how you’re getting from the airport to your destination.

Preparation makes travel easier. But there is a point where planning becomes trying to control an experience that, by its very nature, can’t be completely controlled.

I see itineraries sometimes that make me tired just reading them. Rome. Florence. Venice. Cinque Terre. Tuscany. Amalfi. Ten days.

Just don’t do it to yourself. Italy isn’t going anywhere. You don’t need to conquer it. You need to experience it.

One of the reasons I design my own tours the way I do is because I want people to have time to actually be somewhere. Sit down. Eat. Talk. Walk around. Have an afternoon without wondering what they’re supposed to be doing next.

Travel shouldn’t feel like completing a checklist.

Leave a Little Room for Italy to Be Italy

After years of traveling here and bringing groups here, I’ve noticed something: The people who seem to enjoy Italy the most aren’t necessarily the people who have the perfect weather, the perfect hotel room or the perfectly executed itinerary.

They’re the people who can laugh when something changes. They’re the ones who shrug and say, “Okay. What do we do instead?”

They’re curious. They’re flexible. And they don’t allow one inconvenience to become the story of the entire day. Let alone the entire trip.

Because things will happen. Your train may be late. You may get rained on. You might get lost. Your restaurant may be closed. You may order something you don’t like. And you might have to change your plans completely.

Prepare for your trip. Do your research. Make your reservations. Pack the comfortable shoes. But also pack a little patience, a sense of humor and a willingness to change course.

Leave a little room for Italy to be Italy.

Because very often, that’s where the best stories begin.