Italy welcomes visitors with open arms, but first-time travelers often stumble into common pitfalls that transform dream vacations into stressful experiences. Approximately 134 million international tourists flocked to Italy in 2023, representing a significant recovery from pandemic levels. However, beneath those impressive statistics lies a harsh truth that many discover too late: visiting Italy requires more strategic planning than most other destinations.
Walking through Rome’s ancient streets or gazing at Florence’s Renaissance masterpieces should feel magical, not overwhelming. Yet countless travelers return home with stories of missed opportunities, wasted money, and exhausting days that could have been avoided with better preparation. Let’s dive into the seven biggest regrets that plague first-time visitors to Italy.
Packing Like I Was Moving Permanently
Unless you’ve paid for private transfers and someone’s dropping you at the door of every hotel, you’re going to be hauling your own bags on and off trains, up steps, across cobbled streets, through crowds, over bridges in Venice. It’s not fun with a massive suitcase. My first mistake became painfully obvious the moment I stepped off the train in Florence.
There’s nothing quite like the regret of hauling a bulky suitcase over uneven cobblestone streets in Florence, squeezing past Vespas and tourists while your wheel gets stuck for the tenth time. The romantic vision of strolling through historic piazzas quickly dissolved into a sweaty nightmare of logistics. Italian cities weren’t designed for modern luggage, and their narrow medieval streets punish over-packers mercilessly.
I always try to travel with carry-on only, even for summer trips of 10 days or more. If you’re checking a bag, then try not to bring a carry-on suitcase too. You end up living in the same outfits anyway – comfy things that cope well with heat and sweat, plus one or two smarter pieces for evenings.
Trying to See Everything in One Trip
American travelers in Europe tend to be the worst offenders. Two days in Rome followed by a day in Florence, a day in Venice, and trying to cram in everything along the way. This approach transforms Italy from an immersive cultural experience into an exhausting race against time.
To avoid packing in too much, we budget a minimum of two weeks to travel in Italy. If you have anything less than that you should take a more leisurely trip. The reality hits hard when you realize that each major city deserves at least three full days to appreciate properly. Rome alone could occupy an entire week without running out of fascinating discoveries.
Choose one of the major cities that you are dying to see and stay there. Seriously, one is enough. Even in a city as small as Venice you will have more than enough to keep you occupied as long as you take your time and really immerse yourself. The most memorable travel experiences happen when you slow down enough to absorb the atmosphere, not when you’re rushing between train stations.
Skipping Advance Reservations for Major Attractions
In Italy, waiting in line feels like a sport and national pastime, all rolled into one; translation, you wait in line for anything and everything. No joke, I waited in line for fruit, FRUIT, from the grocery store. And this wasn’t some rare dragon and passion fruit hybrid that is grown in the deep reaches of space, it was an apple. This cultural reality extends to every major tourist attraction.
Generally, you can expect a lot of museum closures on Mondays in Italy, from the Uffizi in Florence to the Borghese in Rome. Not all museums in Italy follow this rule – for example, Pompeii is open daily, and the Vatican Museums are closed most Sundays – but it’s good to keep in mind.
Why not attend a service instead of standing in line for hours and paying to enter the Duomo just to be hurried through the cathedral because it’s time for the next quota of visitors? Everyone is invited to attend and politely observe, regardless of their religious views or background, and it’s absolutely free. This insider tip reveals how locals navigate their own cities more intelligently than tourists.
Underestimating the Reality of Overtourism
Venice is an epicentre of overtourism, with visitor numbers overwhelming the capacity of the lagoon-locked city. Roughly 70% of international tourists are concentrated on only one percent of Italy’s territory, creating crushing crowds in the most famous destinations.
The Italian capital, among the most affected by overtourism, faces a significant challenge for the management of the already densely populated historic centre. According to Bankitalia, the number of people present daily in the center of Rome, considering residents, students, workers, and tourists, exceeds 21 thousand per km², ten times the density of the rest of the Municipality.
The city, which receives approximately 10-15 million international visitors annually, has implemented several strategies to address the issue. Starting in April 2024, Venice introduced an entry fee for day-trippers to discourage overcrowding during peak seasons. These measures reflect how seriously overtourism affects daily life for both visitors and residents.
Not Bringing Enough Cash
While credit cards are fairly widely accepted in Italy in 2025, it’s best to be prepared with cash at all times! Small items, like coffee and gelato, are almost exclusively paid for in cash. And, you never know when you’ll happen across a cash-only restaurant, tourist attraction, or even a hotel. This lesson becomes expensive quickly when you’re stuck without euros.
Italy is a forward-thinking country; therefore, credit and debit cards are accepted in most places. However, if you are wondering, “Do I need to take Euros to Italy?”, know that there are times when you can only pay for things, usually small items like gelato and coffee, with cash. Without extensive research, you never know when the next hotel, tourist attraction, café, or restaurant will be a cash-only establishment. So, it makes sense to go prepared with some spending money in cash and some on your plastic.
The most frustrating moments happen when you discover that perfect little trattoria or stumble upon an incredible gelato shop, only to realize they don’t accept cards. Italian culture still values cash transactions, especially for small purchases, and tourists who ignore this reality find themselves constantly searching for ATMs instead of enjoying their experiences.
Focusing Only on the Famous Cities
The countryside in Italy is special, and too often it’s ignored by foreign visitors. It shows you a truly different side of Italy, away from the tourist hordes, which sometimes feels like going back in time. The most authentic Italian experiences often happen in places that don’t appear on Instagram feeds.
Lake Como gets all the attention, thanks in part to George Clooney, but I’m a big fan of Lake Orta, which is smaller, cleaner, and much more local. Lake Maggiore and Lake Iseo are two other good options. These alternatives offer the same stunning beauty without the crushing crowds that make photography impossible and meals overpriced.
While iconic hubs slowed, Italy’s lesser-known regions saw more attention in 2025: Puglia with its whitewashed towns, beautiful beaches, and iconic trulli houses, the region is booming as travelers seek authenticity. Le Marche often called “the new Tuscany,” offers rolling hills, Renaissance towns, and coastal escapes – but without the heavy crowds and low prices. Sardinia once overlooked by Americans, it’s now appearing on more itineraries thanks to its pristine beaches, rugged landscapes, and growing luxury scene.
Not Learning Basic Italian Phrases
This doesn’t mean you need to spend 40 hours on Duolingo or be able to order a full meal in perfect Italian. But a few basic phrases go a long way. Even just opening with “ciao”, “buongiorno”, or “buonasera” before asking if someone speaks English – “parla inglese?” – sets a completely different tone. It shows respect.
You’re not just launching into English and expecting everyone to accommodate you. I always think of it this way: if someone came to your country and immediately started speaking to you in their language, you’d probably feel a bit thrown, too. This small effort transforms interactions from transactional to genuinely warm.
It’s polite, it’s fun, and Italians are generally incredibly gracious about visitors attempting to speak their language. Even butchered pronunciation is met with encouraging smiles and patient corrections. The difference in service, recommendations, and overall treatment becomes immediately apparent when you show respect for the local culture through language attempts.
The country rewards travelers who approach it thoughtfully rather than those who treat it like a theme park to be conquered in a week. My regrets taught me that Italy deserves better from its visitors, and visitors deserve better experiences when they show up prepared. Did you expect that planning could make such a dramatic difference in experiencing la dolce vita?