I'll be honest – when I first touched down in Italy, I was that wide-eyed traveller. The kind who packs way too much, sticks to a rigid itinerary, and trusts Google Maps over gut instinct, even when it sends you through cobblestone backstreets with zero signage.
I still remember standing in Rome, confused about why my margherita pizza didn't taste like the “authentic Italian” one back home. It wasn't bad – it was better. Just… not what I expected. That entire trip was a dream, but it was also a wake-up call.
Italy isn't just a destination. It's a rhythm. One you have to ease into – whether you're backpacking through Tuscany, booking a day tour of Venice's canals, or catching the sunset in Cinque Terre after a sweaty coastal hike. The magic happens when you stop rushing and let Italy lead.
Over the years, I've made all the classic mistakes: wearing the wrong shoes in Florence, assuming Milan was “just fashion,” missing that very last train in Cinque Terre because I thought “it'll wait.” (It won't.)
So if you're planning your first (or fifth) Italian escape, I've got you. These are the things I wish someone told me – realistic, experience-backed tips covering the cultural nuances, travel essentials for Italy, and those small but mighty details that can make or break your trip.
Because in Italy, it's not just about what you see – it's about how you see it.
Rushing Through Too Many Cities
Throwback to one of my first trips in Europe – Cinque Terre, Italy
On paper, hitting 5 cities in 8 days sounds efficient. In reality? Exhaustion, blurred memories, and zero meaningful moments. Italy isn't meant to be speedrun. Trains are great, but spending your trip transferring instead of exploring can leave you wondering what you actually saw.
Do this instead: Pick fewer cities and give them time to breathe. Spend three days in Florence instead of one. Or stay in a small town like Lucca or Matera and experience Italy outside the usual tourist flow. The slower your pace, the richer your experience.
Eating Only Near Major Attractions
Italian, anyone?
Walk 5 minutes from any major landmark in Rome or Florence and you'll find the price of spaghetti drops and the quality skyrockets. Yet it's astonishing how many tourists sit down for frozen lasagna near the Trevi Fountain and wonder why the food doesn't feel “authentic.”
Do this instead: Follow locals. If a place has a laminated menu in five languages, keep walking. The best meals I've had in Italy came from hole-in-the-wall trattorias with no English signage and a grandmother cooking in the back. Bonus: house wine that costs less than bottled water.
Ignoring Local Customs and Etiquette
Italy has its own rhythm, and while it's forgiving, there's cultural nuance worth knowing. I once got a side-eye in Milan for ordering a cappuccino after lunch—apparently, it's strictly a breakfast drink. And good luck finding dinner before 7:30 PM in some parts of the country.
Do this instead: Greet with a cheerful “Buongiorno,” dress modestly when visiting churches, and don't expect a check to appear without asking for it (“Il conto, per favore”). Small gestures go a long way.
Underestimating Train Travel Logistics
Before I knew better, I assumed train travel in Italy was as simple as showing up with a ticket and hopping on. It's not.
My first rookie mistake? Not validating my paper ticket in one of those tiny yellow machines at the station. I watched my train to Florence roll away while I stood there, ticket in hand and completely confused. That fine I later got? Not exactly a souvenir.
In reality, Italy's train system is one of the best in Europe – efficient, scenic, and relatively affordable. But it comes with quirks that can trip up even seasoned travellers. If you're planning to explore Italy by train (and maybe hop over to France or Spain while you're at it), it pays to prep more than just your seat reservation.
Apps like Trenitalia and Italo are great for buying tickets, checking platforms, and avoiding long lines. But the real travel wisdom comes in knowing the flow of your day. I've learned to think beyond just the train journey – like what time of day I'll be hauling my backpack through crowded platforms, how far the station is from my accommodation, or where I can grab lunch before the next connection. For example, exploring Italy and Spain back to back sounds dreamy, but not if you underestimate travel time and energy.
Trust me, nothing kills that European travel romance faster than wandering hangry in a town square with no clue where your Airbnb is.
When I planned a multi-country trip through Europe by train, I thought bouncing from Venice to Nice to Barcelona sounded perfect. But back-to-back travel days without buffer time? Exhausting. Now, I build in pauses – not just between destinations, but between experiences.
So if you're dreaming of exploring Italy and Europe by train, map the full journey – not just where the train takes you, but what you'll need to feel grounded, fed, and rested on the other side.
Skipping Venice or Staying Only A Night
A lot of people treat Venice like a box to check: pop in, take a gondola selfie, and head out. I get it – Venice can feel overwhelming and overcrowded, especially if you're only seeing it through the lens of St. Mark's Square and overpriced gelato. But I decided to slow down and give it a second shot, staying in a quieter part of town and walking its hidden corners at sunrise. That's when the magic started.
If you're curious about going deeper into this floating city, taking up a couple of Venice private tours offers a way to bypass the surface-level experience and connect with the city's quieter, more storied side.
Overpacking (Literally and Figuratively)
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. I've been that person – sweating through a narrow alley, silently cursing every “just in case” outfit I packed. If you're backpacking through Italy or even just traveling light, trust me: less is more.
But overpacking isn't just about luggage. It's also about stuffing your itinerary with too many “must-sees” and not leaving any space to breathe. Italy isn't a checklist. It's the kind of place where your best memories might come from a random espresso stop in a sleepy piazza, or wandering into a local art gallery you didn't plan to visit.
Here's what I've learned:
- Pack by layers, not looks. Weather shifts fast, especially if you're going from Rome to the Dolomites or Venice to Naples.
- Bring one pair of solid, broken-in walking shoes. If you're backpacking Italy, comfort wins over style every time.
- Plan flex time. Leave space in your schedule to linger. That spontaneous detour to a vineyard or that sunset over a quiet village? That's the real magic.
The lighter your bag and the looser your plan, the more open you are to the unexpected—which, in Italy, is often where the best moments live.
Thinking Every Town Is Like Rome
Rome is loud, busy, and full of grandeur. That doesn't mean all of Italy is. Tuscany is slower and sleepier. The Dolomites are alpine calm. Naples? Wildly different energy. Expecting every place to behave the same will leave you confused and possibly disappointed.
Do this instead: Let each region speak for itself. Don't compare the espresso in Bologna to that in Palermo—it's not supposed to be the same. Embrace the differences.
Missing the Seasonal Sweet Spots
If your trip is in July or August, prepare for crowds and serious heat. I once stood in the Uffizi for two hours just to glimpse The Birth of Venus through a sea of selfie sticks.
Do this instead: Visit during shoulder seasons – late April through early June, or mid-September through October. Fewer tourists, gentler weather, and lower prices make it easier to actually connect with the country. If you're planning your trip around Italy in shoulder season sweet spots, you'll thank yourself later.
Treating Italy Like a Checklist
It's tempting to sprint through Italy with a hit list of must-sees: the Vatican, the Leaning Tower, Pompeii, and that Amalfi Coast cliff photo that everyone else has. But at some point, you start forgetting what you came for in the first place.
I've found that the trips I remember most are the ones where I allowed room for detours, unplanned espresso breaks, or chats with locals at a market. There's real psychological value in choosing novelty and slowness over structure – how novelty in travel boosts mental clarity is something researchers are actually studying now, and it completely tracks with my experience.
Italy is a place that asks you to slow down, savor, and look twice. It's easy to fall into tourist traps – both literal and mental – but with a little awareness, you can avoid the obvious mistakes and find your own kind of magic.
Whether it's your first visit or your fifth, Italy always has more to teach you – if you're paying attention.
