I Visited Italy for the First Time and Left With 5 Big Regrets
Italy is one of those destinations that lives rent-free in the imagination long before you ever set foot there. The gondolas, the ancient ruins, the pasta, the piazzas — it is easy to assume the country will take care of the magic all on its own. But as one travel reporter discovered on her very first Italian adventure in October 2022, even a dream destination can produce real regrets when the planning goes sideways.
During a two-week backpacking trip through Europe, she spent six days traveling between Venice, Rome, and Milan. She was one year into her career as a travel reporter, optimistic, and admittedly underprepared for some of the realities of first-time travel in Italy. What followed was a trip full of beauty — and a handful of lessons she wishes she had learned before boarding the train.
If you are planning your first trip to Italy, consider this your honest, firsthand guide to the mistakes worth avoiding.
1. Spending Too Little Time in Each City
Six days across three major Italian cities sounds reasonable on paper, but in practice it left almost no room to breathe. Venice, Rome, and Milan each deserve far more than a rushed overnight or a frantic two-day sweep. When you are constantly packing and unpacking, calculating train times, and orienting yourself to a new neighborhood, you lose the unhurried pace that makes Italy so special in the first place.
The lesson here is simple but easy to ignore when you are excited and trying to see everything: less is more. Spending four or five days in a single Italian city allows you to wander without an agenda, discover a neighborhood café that never makes it onto any top-ten list, and actually feel like you belong somewhere rather than just passing through.
2. Treating the Colosseum Like a Box to Check
The Colosseum is one of the most recognized structures on earth, and for good reason. Its scale is genuinely staggering, and its history is extraordinary. But visiting it the way most first-timers do — joining the enormous crowds, snapping a photo from the outside, shuffling through with thousands of other tourists — can leave you feeling surprisingly hollow.
She regretted not digging deeper before she arrived. Booking a guided tour that takes you inside the arena floor, or visiting early in the morning before the crowds peak, transforms the experience entirely. Context matters enormously at a site like this. Without understanding what happened within those walls and who built them, the Colosseum risks becoming just another overexposed landmark rather than the profound historical site it truly is.
3. Becoming the Annoying Tourist in Venice
Nobody thinks of themselves as the annoying tourist — right up until the moment they become one. In Venice, that moment arrived. The city is breathtakingly beautiful and also genuinely fragile. It is a living, breathing place where real people reside, work, and navigate daily life alongside an overwhelming flood of visitors.
Common tourist habits that seem harmless — sitting on historic steps, eating in restricted areas, dragging luggage across narrow bridges during busy hours — create real friction for residents. Venice has implemented rules and even fines to protect its character and the wellbeing of its community. Being mindful of those guidelines is not just about following the rules. It is about respecting the place you came to admire.
4. Only Spending One Night in Milan
Milan is often the city people sacrifice when an Italy itinerary gets tight. It lacks the obvious ancient grandeur of Rome or the waterway romance of Venice, so it tends to get shortchanged. One night is barely enough time to recover from travel fatigue, let alone explore what the city actually offers.
Milan rewards the curious traveler. Beyond the fashion district and the Duomo, it has world-class art, including Leonardo da Vinci's The Last Supper, which requires advance booking weeks or even months ahead. It has vibrant neighborhoods like the Navigli canal district, exceptional food culture, and an energy that feels distinctly different from the rest of Italy. Skimming the surface with a single overnight stay meant leaving with very little of what Milan genuinely had to give.
5. Not Booking Key Experiences Far Enough in Advance
Italy's most iconic experiences — viewing The Last Supper, skipping the queue at the Vatican Museums, getting a table at a beloved local trattoria — are not things you can casually decide to do the morning you arrive. They require planning, sometimes weeks or months in advance, and this is one of the most common and avoidable mistakes first-time visitors make.
Showing up without reservations at peak attractions often means long lines, sold-out tickets, or disappointment. The good news is that the fix is entirely within your control. Build your must-do list before you book your flights, research what requires advance tickets, and lock those reservations in early. Your future self, standing inside the Vatican with a reserved entry time while others queue for hours, will be deeply grateful.
What to Take Away Before Your First Trip to Italy
Every traveler makes mistakes, and a first trip to a new country almost guarantees a few. That is not a reason to feel defeated — it is a reason to travel smart. Italy is generous with second chances, and most of these regrets point toward the same underlying truth: slow down, plan ahead, and stay curious beyond the obvious highlights.
Give each city the time it deserves. Do your research before you arrive. Treat the places and people you encounter with genuine respect. And if you can, go back. Italy has a way of rewarding visitors who return with a little more wisdom than they had the first time around.