The Biggest Mistake People Make When Planning an Italy Trip

Sometimes the best travel memories begin with a spritz, a little bowl of salty potato chips, and nowhere else you need to be.

Planning an Italy itinerary can be one of the most exciting parts of preparing for your trip. It's also where I see travelers make the biggest mistakes. One of the hardest parts of my job as a travel advisor isn't finding great hotels or recommending incredible restaurants—it's convincing excited travelers to slow down.

Not long ago, someone asked me if they could visit Rome, Florence, Venice, Milan, Lake Como, Cinque Terre, the Amalfi Coast, and Sicily...all in ten days. I smiled and said, "I want you to see every one of those places. Just not on this trip."

I completely understood where they were coming from. For many people, a trip to Italy is something they've dreamed about for years. Maybe it's a once-in-a-lifetime vacation, or maybe they won't be back for another five or ten years. When that's the case, it's only natural to want to squeeze in as much as possible. The problem is that the more destinations you add, the less time you have to actually experience them.

Vacation Days Aren't the Same as Travel Days

One of the biggest mistakes I see people make is forgetting that travel days aren't really vacation days. Let's say your flight lands in Rome at 7:00 a.m. after 15 to 24 hours of traveling. Please don't schedule your "must-do" Vatican tour for 10:00 that morning.

Flights get delayed. Immigration lines can be unpredictable. Jet lag is real. And after an overnight flight, I promise you'll enjoy wandering through the Vatican a whole lot more when you're awake.

The same goes for moving between cities. People often look at a two-hour train ride and think, "Perfect! That's basically no travel time." But the train ride is only part of the equation. You still have to pack your suitcase, check out of your hotel or apartment, get to the train station, wait for your train, arrive in a new city, get to your accommodation, check in, unpack, and figure out where everything is. Before you know it, half the day has disappeared. That isn't a bad thing—it's simply the reality of travel. The mistake is pretending those hours don't exist when you're planning your itinerary.

That's why I almost always recommend spending at least three nights in each destination. It gives you enough time to settle in instead of feeling like you're constantly living out of your suitcase.

My Upcoming Italy Trip Is a Good Example

When I started planning my own trip this September, I didn't begin by picking cities.

I started by looking at flights. The best airfare happened to be in and out of Rome, so that's where the trip began. I've been fortunate enough to visit Rome more times than I can count, and I absolutely love it, but this time I wanted the focus to be somewhere new.

That led me to Bologna and Parma. Suddenly, without really trying, the trip became centered around food.

I'll be meeting with food tour companies, visiting a Parmigiano Reggiano producer, connecting with local guides, and exploring experiences I can confidently recommend to future clients. The train connections between the cities also made the itinerary simple without requiring a rental car.

Could I have squeezed in another destination? Absolutely. But doing so would have meant giving up time in the places I was most excited to experience. Could I have added Florence for a night? Probably. Should I? I don't think so. I'd rather come home wishing I had one more destination than feeling like I never truly experienced the ones I visited.

The Best Trips Leave Room for Surprise

My favorite travel memories have almost never come from the attractions I planned months in advance. They've come from the moments I never expected. A lunch that somehow turned into three hours because the owner brought out homemade limoncello and insisted we stay for dessert. Learning how coffee is roasted from the owner of a tiny coffee shop in Naples. Stumbling across a neighborhood festival because I wasn't rushing to make the next reservation. Those moments don't happen when every hour of your day is scheduled.

One of the first things I add to every itinerary is...nothing. I intentionally leave empty space. Not because I don't know what to fill it with. Because I know Italy will.

Every Great Itinerary Starts With the Same Question

When someone reaches out to me about planning an Italy trip, I don't start by asking which cities they want to visit. I start by asking what kind of trip they want to have.

If your dream trip is all about fashion, luxury shopping, and glamorous lakeside towns, your itinerary is going to look very different from someone whose priority is eating the best pasta of their life, drinking wine in the countryside, or finding the perfect pizza in Naples.

There isn't one "perfect" Italy itinerary. There's only the itinerary that's perfect for you.

That's why I don't build trips based on where I would go. I build them around the experiences my clients want to have.

What I Hope You Remember

Of course I want you to see the Colosseum. I want you to tour the Vatican, climb the Duomo, wander through Venice, and eat incredible pasta. But years from now, I don't want you scrolling through your camera roll wondering, "Where was this again?"

I want you to remember the family-run restaurant where lunch lasted three hours. The owner who poured one more glass of limoncello before you left. The neighborhood café where they recognized you on your second visit. The quiet street you wandered down simply because you had nowhere else to be. Those aren't the moments that happen around your itinerary.

They are the itinerary.