I’ve been traveling to Italy for over two decades, both as a tourist and as a journalist covering everything from politics to pasta. In that time, I’ve made just about every mistake in the book – and watched countless other visitors do the same. Italy has a way of seducing you with its beauty and charm while simultaneously baffling you with its quirks and complexities. Even seasoned travelers can find themselves caught off guard by the nuances of Italian culture and customs.

As I sit here in a sun-drenched piazza, sipping my third espresso of the morning and watching the daily dance of locals and tourists, I can’t help but reflect on all the missteps I’ve witnessed – and committed myself. So consider this your insider’s guide to avoiding the most common pitfalls that can turn your dream Italian vacation into a comedy of errors.

First and foremost, let’s talk about timing. I’ll never forget my first trip to Rome in August, fresh out of college and blissfully ignorant of European vacation schedules. I arrived to find a ghost town – well, a ghost town swarming with other confused tourists. Most restaurants were shuttered, many shops closed, and the few attractions that remained open were packed to the gills with sweaty, irritable visitors.

The locals, it turns out, had wisely fled to the coast or the mountains to escape the suffocating heat. I spent a week alternating between standing in endless lines and hiding in my stuffy hotel room, dreaming of gelato and air conditioning. Learn from my mistake: avoid traveling to major Italian cities in August like the plague. Unless, of course, you enjoy paying premium prices for reduced services and the unique experience of being crammed into the Sistine Chapel with what feels like half the world’s population.

Speaking of crowds, let’s discuss the second cardinal sin of Italian travel: failing to book ahead. I’ve lost count of the number of times I’ve encountered crestfallen travelers outside the Uffizi or the Vatican Museums, having just been told that the next available entrance slot is in approximately never.

Italy’s most famous attractions are popular for a reason, and in high season, showing up without a reservation is about as effective as trying to get into a Michelin-starred restaurant on a Saturday night in your pajamas. Trust me, I’ve tried both (though the latter was for a different article altogether). Do yourself a favor and book your must-see sights well in advance. Your future self will thank you as you smugly bypass the hours-long queues.

Now, let’s delve into the realm of culinary faux pas, a topic close to my heart (and stomach). Italian food is revered worldwide for good reason, but it’s also surrounded by a web of unwritten rules that can trip up even the most well-meaning foodie. I’ll never forget the horror on my waiter’s face in Bologna when I asked for a cappuccino after dinner. You’d have thought I’d suggested putting pineapple on pizza (another cardinal sin, by the way).

In Italy, cappuccino is strictly a morning drink. After noon, you’ll want to stick to espresso if you need a caffeine fix. And while we’re on the subject of coffee, forget about grabbing it to go. The idea of sipping your espresso from a paper cup while walking down the street is enough to make an Italian barista weep. Coffee is meant to be savored standing at the bar or, if you must, sitting at a table (though be prepared to pay extra for the privilege).

But the coffee conundrum pales in comparison to the pasta pitfalls that await the unwary. I once witnessed a friend confidently order spaghetti Bolognese in a trattoria in Rome, only to be met with a mixture of confusion and disdain. Spaghetti Bolognese, it turns out, is about as authentically Italian as fortune cookies are Chinese.

In Bologna, the home of ragù, you’ll find tagliatelle al ragù, a rich meat sauce served with flat, ribbon-like pasta – never spaghetti. And don’t even think about asking for extra parmesan on your seafood pasta. I made that mistake once and thought the chef was going to come out of the kitchen and personally escort me back to America.

Speaking of regional specialties, one of the biggest mistakes travelers make is treating Italy as a monolithic culinary entity. Each region, each city, even each village has its own specialties and traditions. Ordering risotto in Naples or pizza in Milan isn’t just a culinary faux pas – it’s a missed opportunity to experience the incredible diversity of Italian cuisine.

I’ll never forget the time I spent a week eating my way through Sicily, only to realize on my last day that I hadn’t once encountered a dish I recognized from the “Italian” restaurants back home. From pasta con le sarde in Palermo to arancini in Catania, every meal was a delicious revelation. So do your research, ask locals for recommendations, and be adventurous. Your taste buds will thank you.

Now, let’s talk about a mistake that’s as much about etiquette as it is about comfort: dressing inappropriately. I learned this lesson the hard way on my first visit to the Vatican. Young, naive, and woefully underdressed in shorts and a tank top, I was turned away at the door of St. Peter’s Basilica. I ended up having to buy an overpriced shawl and a pair of truly hideous palazzo pants from a nearby souvenir shop just to gain entry.

Many churches and religious sites in Italy have strict dress codes – no bare shoulders, no shorts, no miniskirts. And while you might be tempted to don your favorite Hawaii-print shirt and sandals with socks (please don’t), Italians tend to dress more formally than many tourists are used to. You don’t need to pack your tuxedo, but leaving the flip-flops at home and throwing in a few smart-casual outfits will help you blend in better and might even get you better service in restaurants and shops.

I’ll move on to a mistake that’s less about cultural faux pas and more about personal comfort and safety: overpacking. I’ve seen tourists struggling to haul enormous suitcases up the narrow, cobblestone streets of Positano and over the countless bridges of Venice. Trust me, there’s nothing that will make you resent that extra pair of shoes more than trying to drag them up six flights of stairs to your charming (but elevator-less) pensione.

Italy’s ancient cities, with their uneven pavements and labyrinthine alleys, were not designed with rolling luggage in mind. Add to that the fact that many trains have limited storage space and you’ll quickly realize that less is more when it comes to packing for Italy. I’ve learned to travel light, relying on a capsule wardrobe and the knowledge that if I really need something, I can probably buy it there (and end up with a great souvenir in the process).

Now, let’s discuss a mistake that can not only put a dent in your wallet but also potentially land you in hot water with the law: ignoring local regulations. Italy’s cities are increasingly cracking down on tourist behaviors that they deem disrespectful or disruptive. I’ll never forget witnessing a group of tourists being fined for picnicking on the Spanish Steps in Rome. They were baffled, insisting they were “just eating lunch,” but the police were unmoved.

From bans on sitting on monuments in Florence to prohibitions against swimming in Venice’s canals (yes, people have tried), it’s crucial to familiarize yourself with local rules. This extends to less obvious regulations too, like restrictions on where you can eat and drink in public in certain cities. A little research can save you a lot of embarrassment – and money.

Speaking of money, let’s talk about a mistake that’s becoming increasingly common in our digital age: relying too heavily on cards and digital payments. While Italy has made strides in embracing cashless transactions, especially in larger cities and tourist areas, cash is still king in many parts of the country.

I learned this the hard way on a road trip through rural Tuscany. After a long day of driving, I arrived at a small, family-run agriturismo, ready for a home-cooked meal and a good night’s sleep. When I tried to pay with my credit card, the owner looked at me as if I’d offered to barter with seashells. Cash only, no exceptions. Luckily, I had just enough euros to cover the bill, but it was a close call.

Always carry some cash with you, especially when venturing outside major cities. Not only will it save you in situations like mine, but it’s also handy for small purchases, tipping, and those irresistible markets where you’ll find everything from fresh produce to antique treasures.

This is another mistake that’s less tangible but no less important: rushing through your itinerary. I get it – Italy is a treasure trove of art, history, and culture, and you want to see it all. But trying to cram Rome, Florence, Venice, and the Amalfi Coast into a week-long trip is a recipe for exhaustion and disappointment.

I’ve been guilty of this myself, particularly on my early trips. I’d run from the Colosseum to the Vatican, from the Uffizi to the Duomo, checking sights off my list like a manic scavenger hunter. It wasn’t until I slowed down and allowed myself to get lost in the back streets of Venice, or spend an entire afternoon people-watching in a Roman piazza, that I truly began to appreciate the magic of Italy.

The Italy of glossy travel brochures exists, to be sure, but the real heart of the country – the Italy that will steal your heart and keep you coming back – reveals itself in the quiet moments between the grand attractions. It’s in the elderly men playing cards in a sun-dappled square, the waft of fresh bread from a neighborhood bakery, the impromptu opera performance in a tiny Neapolitan alley.

So resist the urge to over-schedule. Leave room for spontaneity, for long lunches that stretch into aperitivo hour, for aimless wanderings that lead to unexpected discoveries. Some of my most cherished memories of Italy are of the times when I had nowhere in particular to be.

Finally, let’s address perhaps the most fundamental mistake of all: failing to learn a bit of Italian. Yes, in tourist hotspots you can generally get by with English. But making an effort to speak even a few words of Italian can transform your experience from that of a tourist to something closer to a welcomed guest.

I’ll never forget my first attempt at ordering in Italian at a tiny trattoria in Rome. My mangled pronunciation of “spaghetti alle vongole” elicited a hearty laugh from the waiter, but it also broke the ice. By the end of the meal, he was teaching me Roman dialect and insisting I try his nonna’s homemade limoncello.

You don’t need to be fluent – even a simple “buongiorno” (good morning), “grazie” (thank you), or “il conto, per favore” (the bill, please) can go a long way. Not only is it respectful, but it often leads to warmer interactions and maybe even some insider tips from locals.

As I wrap up this rather lengthy discourse on what not to do in Italy, I’m struck by a realization. These “mistakes” – from culinary faux pas to overscheduling – are all part of the learning process, the inevitable stumbles we make as we navigate a culture different from our own. They’re the stories we laugh about later, the experiences that shape our understanding and appreciation of this complex, captivating country.

So yes, try to avoid these pitfalls if you can. But also remember that perfection isn’t the goal. Italy, with all its beauty and chaos, its rules and its contradictions, has a way of humbling even the most prepared traveler. Embrace the mishaps along with the triumphs. Order that cappuccino at dinner if you really want it. Get gloriously lost in Venice. Butcher the pronunciation of “bruschetta” (it’s “broo-SKET-ta,” by the way).

Because in the end, the “mistakes” are all part of the adventure. They’re what transform a simple vacation into a journey, a checklist of sights into a rich, multifaceted experience. And isn’t that, after all, why we travel?

So go ahead, book that ticket to Italy. Armed with this hard-won wisdom, you’re bound to have an unforgettable adventure. Just don’t blame me if you end up extending your stay – or planning your return trip before you’ve even left. Italy has that effect on people. Trust me, I know.