I Went to Italy for the First Time and Left With 5 Regrets — Here's What I'd Do Differently
Italy is one of the most romanticized destinations on the planet. The canals of Venice, the ancient grandeur of Rome, the sleek energy of Milan — it all sounds perfect on paper. But for one travel reporter, a six-day whirlwind through these iconic cities in October 2022 came with a side of hard-earned lessons. From becoming the exact kind of annoying tourist she never wanted to be, to rushing through cities that deserved far more time, the trip left her with five genuine regrets.
If you're planning your first trip to Italy, this honest account might be the most useful thing you read before you book your flights. Here's what went wrong — and exactly how to avoid making the same mistakes.
1. Spending Too Little Time in Each City
Six days across three major Italian cities sounds manageable until you're actually standing at the base of the Colosseum with three hours on the clock before your next train. Venice, Rome, and Milan each deserve far more than a rushed stopover, yet that's exactly what a tight itinerary forces you into.
Venice alone could easily fill three or four days of meaningful exploration — not just the busy areas around St. Mark's Square, but the quieter neighborhoods of Cannaregio, the islands of Murano and Burano, and the peaceful early-morning canals before the day-trippers arrive. Rome, with its layers of history stretching back over 2,500 years, is a city where slowing down is the only way to truly connect with what you're seeing.
What to do instead: If it's your first time in Italy, resist the urge to tick off multiple cities. Choose two destinations and give yourself at least three nights in each. Depth beats breadth, especially in a country where the best experiences happen when you're not racing a train schedule.
2. Visiting the Colosseum Without Doing Enough Research
The Colosseum is one of the most visited monuments in the world, attracting millions of tourists every single year. Going in without a solid understanding of its history, layout, and ticketing logistics is a recipe for disappointment — and unfortunately, that's a trap many first-timers fall into.
Long queues, crowds that make it hard to absorb the atmosphere, and a general sense of being shuffled through a landmark rather than experiencing it are common complaints from visitors who didn't prepare. The Colosseum is genuinely extraordinary, but it rewards those who arrive informed and with a plan.
What to do instead: Book skip-the-line tickets well in advance — ideally a guided tour that also covers the Roman Forum and Palatine Hill. Read up on the history beforehand so that what you're seeing actually means something. Consider arriving early in the morning or going on a weekday to avoid the worst of the crowds.
3. Becoming That Annoying Tourist in Venice
There's a particular kind of traveler that residents of Venice quietly dread — the one who treats the city like a theme park, snapping photos in the middle of narrow bridges, slowing down foot traffic, and prioritizing the shot over the experience. It's an easy trap to fall into, especially when you're surrounded by some of the most photogenic scenery in the world.
Venice is a living, breathing city where real people actually live and work. Overcrowding and disrespectful tourist behavior have become serious issues there, and locals are understandably frustrated by visitors who treat it as nothing more than a backdrop.
What to do instead: Be intentional about how you move through Venice. Step aside when taking photos. Explore beyond the main tourist drag. Eat at restaurants where locals actually go rather than the overpriced spots lining the Grand Canal. Engaging with the city respectfully makes for a richer experience anyway.
4. Only Spending One Night in Milan
Milan often gets dismissed as "just a fashion and business city" by travelers who are more drawn to Rome's history or Venice's beauty. But spending only one night there means you barely scratch the surface of what it offers — and you leave with little more than a rushed glimpse.
Milan is home to Leonardo da Vinci's The Last Supper, one of the most remarkable works of art in human history. It has world-class museums, incredible food, beautiful parks, and a design culture unlike anywhere else in Italy. One night is simply not enough to appreciate any of it.
What to do instead: Give Milan at least two nights, ideally three. Book your reservation to see The Last Supper months in advance — spots fill up extremely quickly. Explore the Navigli canal district in the evening, visit the Pinacoteca di Brera, and take time to wander neighborhoods like Isola and Prati.
5. Not Embracing Slow Travel From the Start
Perhaps the biggest regret of all was approaching Italy the way many first-time visitors do — with an ambitious checklist rather than an open mindset. The pressure to see everything in a short time creates a kind of travel anxiety that works against the very spirit of the country.
Italy is fundamentally a place built for lingering. Long lunches that drift into the afternoon. Espresso standing at a bar with no particular place to be. Getting genuinely lost down an alley that doesn't appear on any map. These are the moments that define a great Italian trip — and they're almost impossible to have when you're constantly moving.
What to do instead: Build empty space into your itinerary on purpose. Accept that you won't see everything, and that's completely fine. The Italy you'll fall in love with is found in the unhurried moments, not the checked-off attractions.
Final Thoughts: Make Your First Italy Trip Count
Every traveler makes mistakes, especially on a first visit to a new country. The difference between a trip that frustrates and one that transforms often comes down to a few key decisions made before you ever board the plane. Slow down your pace, do your homework on the major sites, respect the places and people you visit, and give yourself enough time in each city to actually feel it rather than just see it.
Italy will reward you generously for the effort. Go prepared, go curious, and go ready to let the country surprise you — because it absolutely will.