10 Mistakes to Avoid on Your First Trip to Italy

There’s a reason Italy is on so many bucket lists: wandering through ancient streets in Rome, sipping wine in Tuscany, catching the sunset over the Amalfi Coast… it’s every traveler’s dream. But here’s the thing no one tells you, Italy is just as good at teaching you lessons as it is at serving you pasta.

On our first trip, we made more mistakes than we’d like to admit, the kind that leave you hot, tired, and wondering how a dream day in Florence somehow turned into a marathon. From packing the wrong shoes to missing out on must-see sights because we didn’t plan ahead, we learned quickly that a little preparation can make all the difference.

That’s why we put together this list of the most common mistakes travelers make in Italy, including the ones we made ourselves, so you can skip the stress, avoid the tourist traps, and go straight to enjoying la dolce vita.

Mistake #1: Trying to See too Much of Italy in One Trip

We get it, when you finally book that dream trip to Italy, you want to see everything. Rome, Florence, Venice, the Amalfi Coast, Cinque Terre, Milan, Lake Como… it’s tempting to cram it all in. But here’s the reality, Italy is a country that’s meant to be savored, not rushed through like a to-do list.

Packing in too many destinations means you’ll spend more time hauling luggage, catching trains, and figuring out transportation than actually enjoying the places you came to see. You might end up spending a single rushed day in a city that truly deserves three or four. And by the time you get your bearings, it’s time to move on.

Instead, pick two or three regions and explore them at a slower pace. Spend your days wandering side streets, enjoying long meals, and soaking in the atmosphere without constantly checking the clock. Trust us, you’ll remember that lazy morning sipping espresso in a quiet piazza far more than the blur of half-seen landmarks.

Mistake #2: Not Booking Major Attractions in Advance

Italy’s most famous landmarks are on just about everyone’s bucket list, and that means they sell out fast. The Colosseum in Rome, the Vatican Museums, Florence’s Uffizi Gallery, and even popular sites like the Leaning Tower of Pisa can book out days or weeks in advance, especially during peak travel season.

Showing up without a ticket often means wasting hours in line or, worse, missing out entirely. We’ve seen travelers walk away disappointed because the time slots they wanted were gone. And standing in the hot Italian sun for two hours just to get into a museum is not the way you want to spend your vacation.

As soon as you book your flights, make a list of your must-see attractions and buy tickets online directly from the official websites. Not only will you secure your spot, but you can also choose time slots that fit your itinerary perfectly. That way, you spend more time inside enjoying the art, history, and views, and less time waiting to get in.

Mistake #3: Only Visiting the Big 3 Cities

Rome, Florence, and Venice are popular for a reason, they’re full of history, art, and that unmistakable Italian charm. But if you limit your trip to only these three cities, you’re missing out on an entirely different side of Italy.

Italy’s magic isn’t just in its famous landmarks; it’s in the slower-paced coastal towns, the rolling hills of wine country, and the medieval villages where it feels like time has stood still. Places like Cinque Terre, the Amalfi Coast, Bologna, Verona, and Puglia offer incredible scenery, unique local cuisine, and far fewer crowds.

This doesn’t mean you should cram in dozens of cities, you still want to keep your itinerary manageable, but if you have the time, swapping one big city for a smaller town can give you a richer, more balanced experience. You’ll get the best of both worlds, the energy and culture of the big cities and the authenticity and tranquility of Italy’s hidden gems.

Mistake #4: Not Validating Your Train Ticket

If you’re traveling by train in Italy, which we highly recommend, there’s one small step that can cause big problems if you forget: validating your ticket. For certain regional and intercity trains, especially if you have a paper ticket, you need to stamp it in the small machines located on the platforms before boarding.

This process time-stamps your ticket so it can’t be reused, and conductors will check for it during your journey. If you haven’t validated, even if you just bought the ticket and are clearly a tourist, you can be fined on the spot, sometimes €50 or more, payable in cash to the inspector.

The good news is that it’s easy to avoid this mistake. Simply look for the small yellow or green validation boxes near the tracks (or occasionally inside the station) and insert your ticket until you hear a click and see the print. If you’re using an app like Trenitalia or Italo for an e-ticket, you don’t need to validate, but make sure your QR code is ready to show. It’s a tiny detail, but it can save you from a frustrating and expensive lesson.

Mistake #5: Assuming Every Restaurant is Open All Day

In Italy, mealtimes are sacred, and they’re not on the same schedule you might be used to. Many restaurants (especially in smaller towns) open for lunch around 12:30–3:30 PM and then close for several hours before reopening for dinner around 6:30 or 7:00 PM. If you’re wandering around at 4 PM hoping for a big plate of pasta, you might find yourself staring at locked doors and empty dining rooms.

This midday closure is called “riposo” (similar to a siesta in Spain), and it’s part of the Italian rhythm of life. Locals use this time to rest, spend time with family, or simply take a break before the evening rush.

To avoid going hungry, plan ahead. Either eat during standard lunch hours, grab some snacks from a local market to hold you over, or look for cafés, bakeries, or casual bars that stay open all afternoon. In tourist-heavy cities like Rome, Florence, and Venice, you’ll find more places that stay open all day, but they may be pricier and less authentic.

Mistake #6: Overpacking Your Luggage

It’s tempting to pack an outfit for every possible Instagram photo, but hauling an overstuffed suitcase through Italy can turn your dream trip into a workout you didn’t sign up for. Picture dragging it over uneven cobblestone streets, squeezing it onto crowded trains, or lugging it up flights of stairs because your charming centuries-old hotel doesn’t have an elevator. We’ve been there, and it’s not the kind of memory you want to take home (especially after a long day of traveling).

Many travelers underestimate how much walking and moving they’ll do in Italy, and heavy bags just slow you down. The truth is, you’ll probably end up re-wearing your favorite pieces anyway. Pack lighter, focus on versatile clothing you can mix and match, and bring shoes that can handle both sightseeing and a nice dinner. You’ll also want to leave room for souvenirs, like hand-painted ceramics from Positano, leather bags from Florence, or bottles of wine from Tuscany.

By packing smart and light, you’ll spend less time fighting with your luggage and more time enjoying the reason you came to Italy in the first place: the food, the views, and the memories.

Mistake #7: Skipping Travel Insurance

When you’re planning an exciting trip to Italy, it’s easy to see travel insurance as an unnecessary extra until you need it. Lost luggage, flight cancellations, stolen belongings, or even a sudden illness can derail your plans and cost you hundreds (or thousands) of euros. And while Italy’s healthcare system is excellent, non-residents are still expected to pay out-of-pocket if they don’t have coverage.

We’ve met travelers who had to cut their trip short after twisting an ankle, missed entire days in Rome because their bags got lost en route, or spent hours at the police station after a stolen wallet. None of these situations are fun, but they’re much less stressful when you know you’ll be reimbursed.

A good travel insurance policy can cover medical expenses, trip interruptions, and even theft,  giving you peace of mind so you can focus on enjoying Italy. It’s one of those things you hope you’ll never need but will be incredibly grateful to have if the unexpected happens. For the cost of a nice dinner out, you’re essentially buying protection for your entire trip.

Mistake #8: Thinking You Can Drive Anywhere

Renting a car in Italy sounds like the ultimate freedom, winding along the Amalfi Coast, driving through Tuscany’s rolling hills, and exploring charming villages off the beaten path. And in the countryside, it can be an amazing way to see more of the country, but driving in Italian cities is a completely different story.

Many historic centers have ZTL zones, which are restricted areas where only residents or authorized vehicles can enter. These zones are monitored by cameras, and if you accidentally drive into one, even for a minute, you’ll likely get a hefty fine mailed to you back home. Parking can also be nearly impossible in popular cities, and the streets are often narrow, busy, and confusing for first-time visitors.

If you’re planning to visit multiple cities, stick to trains for the urban portions of your trip and rent a car only when you head into rural areas. You’ll save yourself the stress of navigating traffic, avoid expensive parking fees and fines, and actually get to enjoy the scenic drives where Italy’s roads truly shine.

Mistake #9: Ignoring Train Strikes & Schedule Changes

Italy’s train system is one of the best ways to explore the country, but it’s not immune to last-minute hiccups, especially strikes and schedule changes. These can pop up with little warning and can completely derail your travel plans if you’re not prepared.

We’ve never personally been caught in the middle of one (thankfully), but a major strike happened the day after we left,  and it shut down service across large parts of the country. Travelers who didn’t know about it in advance were left scrambling for buses, taxis, or last-minute hotels.

Strikes aren’t uncommon in Italy, and while they’re usually announced ahead of time, the updates are often in Italian and easy to miss. Before each travel day, check the Trenitalia or Italo app for real-time updates. If there’s a strike planned, look for alternate options like buses, private transfers, or simply adjusting your itinerary to stay put another day. A little preparation can keep an unexpected schedule change from ruining your trip.

Mistake #10: Visiting Only in Peak Season

Italy is magical year-round, but if you only plan your trip for the peak summer months of June, July, and August, you’re signing up for the hottest temperatures, the biggest crowds, and the highest prices. While there’s no denying summer in Italy has its charm, the reality is that popular spots like the Amalfi Coast, Cinque Terre, and Venice can feel overwhelmingly crowded, and you may find yourself spending more time dodging tour groups than enjoying the views.

Traveling in shoulder seasons, late spring (April–May) or early fall (September–October), can make a huge difference. You’ll still get good weather, but with fewer crowds, more availability at hotels, and shorter lines for attractions. Even winter has its perks, especially in cities like Rome and Florence, where mild temperatures make sightseeing more comfortable, and holiday markets add a festive touch.

If summer is your only option, just be sure to plan ahead, book early, and schedule sightseeing for early mornings or late afternoons to avoid the midday heat and the busiest crowds.

Final Tips for Planning the Perfect Italy Trip

Italy has a way of capturing your heart, no matter how many times you visit. From the first sip of espresso in a beautiful piazza to the quiet magic of watching the sun set over ancient ruins, every moment feels unforgettable. But as we’ve learned, even the most beautiful trip can be dampened by simple, avoidable mistakes.

By slowing down your itinerary, planning ahead for must-see attractions, embracing smaller towns, and learning the little details of Italian travel etiquette, you can skip the stress and dive straight into la dolce vita. Traveling smarter doesn’t mean losing spontaneity; it just means giving yourself the best chance to soak up Italy’s beauty without the frustration of “I wish we had known.”

So pack your comfortable shoes, keep your mind open to unexpected detours, and let Italy show you why it’s a destination people return to again and again. With the right mindset (and a little preparation), your trip won’t just meet expectations, it will exceed them.