My first trip to Italy was a masterclass in doing almost everything the hard way, the kind of trip where every small decision seemed to backfire in its own unique way, one after another.
I booked the wrong train tickets and only realized once I reached the platform, wore the wrong shoes for cobblestone streets that chewed through them by day three, and walked straight past a restaurant locals clearly loved because I trusted a review app over my own eyes, ending up somewhere forgettable instead.
None of it ruined the trip, but every mistake taught me something, usually the hard way, and I now pass those lessons along to anyone planning their first visit so they can skip at least a few of the missteps I didn’t manage to avoid myself.
This post rounds up the twelve I wish someone had warned me about before I learned them the hard way, from the obvious ones to a couple I genuinely didn’t see coming until I was standing in the middle of them.
If you’re deep in the planning stages already, our Italy packing list guide and Italy outfit ideas across four cities pair well with this post for the practical side of things.
What Made This List
I did not put this list together by reading travel forums or collecting the most common advice online.
Every mistake here is one I have experienced myself or learned the hard way after a trip did not go quite as planned.
Some of these mistakes cost me extra money, while others wasted valuable time that I could have spent exploring somewhere new.
A few seemed small at the time, but they quickly turned into unnecessary stress that could have been avoided with a little more preparation.
Of course, not everything that goes wrong while traveling is within your control. Flights get delayed, weather changes unexpectedly, and plans sometimes have to change. Those situations happen to everyone.
This list focuses on the travel mistakes that you can actually prevent with a little planning and awareness.
Before you finish packing your bags or lock in your itinerary, take a few minutes to read through these common mistakes.
Avoiding even one of them could make your next trip smoother, less stressful, and much more enjoyable from beginning to end.
1. Packing the Wrong Shoes
This is the mistake nearly every first time visitor makes, myself included, and it’s the one that affects your trip the fastest.
What went wrong for me I packed a pair of strappy heeled sandals for my first Rome evening, imagining a romantic stroll near the Trevi Fountain. Italy’s cobblestones had other plans, and I switched to flats within a day.
How to avoid it Pack comfortable, supportive walking shoes as your daily default, and save anything delicate for a single planned evening where you’re not covering much ground.
2. Underestimating How Much Walking You’ll Do
Italian cities are built for walking, and most first time visitors, myself included, badly underestimate how many miles a single sightseeing day actually involves.
What went wrong for me I planned a full day covering the Colosseum, the Roman Forum, and Trastevere without realizing how far apart these areas actually feel on foot by the end of the afternoon.
How to avoid it Build buffer time into your itinerary and don’t over schedule a single day. Two well paced sights beat four rushed ones every time.
3. Not Booking Major Attractions in Advance
I assumed I could show up to the Colosseum and figure out tickets on the spot. I was wrong, and it cost me an entire wasted morning standing in a line that barely moved.
What went wrong for me By the time I reached the ticket counter, same day entry was sold out, and I had to rearrange my whole afternoon around a different time slot two days later.
How to avoid it Book major sites like the Colosseum, the Vatican Museums, and the Uffizi Gallery online well in advance, ideally weeks ahead during peak season.
4. Assuming All Restaurants Near Major Attractions Are Good
Restaurants clustered around tourist landmarks are rarely where locals actually eat, and I learned this after a genuinely forgettable meal within sight of the Trevi Fountain.
What went wrong for me I trusted proximity over research and paid tourist prices for mediocre pasta, while a much better restaurant sat two streets away with barely any wait.
How to avoid it Walk a few blocks away from major landmarks before choosing where to eat, and look for restaurants with menus in Italian first, English second, which tends to signal a more local crowd.
5. Not Validating Train Tickets
This one genuinely surprised me, and I nearly got fined over it without realizing what I’d done wrong.
What went wrong for me On a regional train between cities, I didn’t validate my paper ticket in the small machine at the platform before boarding, and a conductor stopped just short of fining me, explaining the rule as if it was obvious.
How to avoid it Always validate paper train tickets in the yellow or green machines near the platform before boarding regional trains. High speed trains with assigned seats generally don’t require this step, but it’s worth double checking.
6. Renting a Car for City Travel
I rented a car assuming it would give me more freedom moving between Rome, Florence, and other cities. It became one of the most stressful parts of the entire trip.
What went wrong for me Italian cities have restricted traffic zones called ZTLs that are easy to accidentally drive into, and I racked up a fine months after returning home for a violation I didn’t even realize I’d committed.
How to avoid it Use trains between major cities, which are fast, comfortable, and far less stressful. Save a rental car specifically for regions like Tuscany or the Amalfi Coast, where public transport is more limited.
7. Not Dressing Appropriately for Churches
I got turned away from a church in Rome for bare shoulders, standing in line behind other tourists who clearly hadn’t planned for this either.
What went wrong for me I hadn’t packed anything to cover up with, and ended up buying an overpriced scarf from a street vendor just to get inside.
How to avoid it Pack a lightweight scarf or cardigan specifically for church visits. Major sites like St. Peter’s Basilica and the Duomo in Florence enforce dress codes covering shoulders and knees. Our Italy outfit ideas post covers this in more detail city by city.
8. Overpacking Your Suitcase
I packed like I was preparing for a photo shoot on my first trip, and spent the entire vacation dragging a suitcase I could barely lift up narrow staircases.
What went wrong for me I brought nearly double what I actually wore, and hauling an overstuffed bag through cobblestone streets and train stations became its own daily workout I hadn’t signed up for.
How to avoid it Pack a smaller, more versatile wardrobe built around a simple color palette. Our travel checklist and backpacking essentials guide both helped me cut my packing list down significantly on later trips.
9. Trying to See Too Many Cities Too Fast
I originally planned to hit Rome, Florence, Venice, and the Amalfi Coast in eight days, and realized about halfway through how badly that pace was working against me.
What went wrong for me Every city started to blur together because I never had enough time to actually settle in anywhere. I spent more time packing and unpacking than genuinely experiencing each place.
How to avoid it Pick two or three regions instead of trying to cover the whole country in one trip. A slower pace consistently produced better memories for me than a packed itinerary ever did.
10. Not Carrying Cash
I assumed cards would work everywhere, the same way they do at home, and quickly found that assumption wrong in smaller towns and family run restaurants.
What went wrong for me I got stuck at a small trattoria outside Florence with no card machine and barely enough cash to cover the bill, which made for an uncomfortable few minutes at the table.
How to avoid it Carry a reasonable amount of cash, especially for smaller towns, markets, and family owned restaurants that may not accept cards or charge a minimum for card use.
11. Ignoring Regional Differences in Food and Culture
I assumed Italian food and customs would feel roughly the same from city to city.
They don’t, and treating the whole country as one uniform experience meant I missed regional specialties I didn’t even know to look for.
What went wrong for me I ordered the same style of pasta dish in three different cities, not realizing each region actually has its own distinct specialties worth seeking out specifically.
How to avoid it Research what each specific region or city is known for before you go, and ask locals for recommendations rather than defaulting to what worked in the last city you visited.
12. Not Building in Any Downtime
This was the mistake that affected my mood the most by the end of the trip, more than any logistical misstep on this list.
What went wrong for me I scheduled something for nearly every waking hour, and by day six I was exhausted rather than energized, dragging myself through sights I should have been enjoying.
How to avoid it Leave at least half a day unscheduled every few days. Some of my best memories from later Italy trips came from wandering with no plan at all, the same lesson that shaped how I now approach road trips and other longer travel too.
A Few More Practical Notes
A handful of smaller lessons that didn’t need a full section but are worth knowing before you go:
- Tipping isn’t expected the way it is in the US, and a service charge is often already included in the bill
- Tap water is safe to drink throughout Italy, and public fountains in most cities are drinkable too
- Many shops and some restaurants close for a few hours in the early afternoon, especially in smaller towns
- If you’re extending your trip beyond Italy, our Ireland and Scotland itinerary is a good next stop for planning
FAQ
What’s the single biggest mistake first time visitors make in Italy? For me, it was trying to see too many cities too fast.
Rushing between destinations left me exhausted and made every city feel less memorable than it should have, more than any single logistical mistake on this list.
Do I really need to validate train tickets? Yes, and I learned this one the uncomfortable way with a conductor standing over me.
Paper tickets for regional trains need to be validated at the small machines near the platform before boarding, or you risk a fine.
Is it necessary to book attractions like the Colosseum in advance? I’d say it’s essential during peak season. I lost an entire morning to a sold out same day line, and booking online in advance would have saved that whole afternoon.
Should I rent a car in Italy? I’d avoid it for city to city travel and stick to trains instead.
A car makes more sense for regions like Tuscany or the Amalfi Coast where public transport options are more limited, but Italian cities’ restricted traffic zones make driving genuinely stressful.
How much cash should I carry in Italy? I’d recommend carrying enough for a couple of meals and small purchases, especially outside major cities.
Smaller family run restaurants and markets don’t always accept cards, and I got caught out by this more than once.
Final Thoughts
Twelve mistakes, and every single one taught me something I now build into how I plan every trip since, not just to Italy.
The biggest shift wasn’t any single fix. It was learning to slow down, plan the logistics that actually matter, and leave enough room for the unplanned moments that usually end up being the best part of the trip anyway.
If you’re still working out the rest of your itinerary, our best places to travel this year and dream vacations bucket list are good places to keep planning once Italy is sorted.
Whatever mistakes you end up making on your own trip, most of them make for a pretty good story afterward anyway.
