How hard can planning your first Italy trip be? You pick what you want to see, when and how you want to go, then set things in motion. Except, plans that look great on paper have a tendency to buckle when faced with the reality of picking the right accommodations or organizing transportation once you land.
Want to avoid the most common mistakes? Then start planning for a trip that you’ll actually enjoy instead of one with a great-looking yet impossible itinerary. Here’s what to avoid and what to do instead.
Trying to See and Do Too Much in One Trip
First-time visitors, especially if they come from larger countries like the USA and Canada, tend to take one look at Italy’s comparatively much smaller size and think they’ll have enough time to experience half the country in ten days.
While it’s true that it takes only a couple of hours via high-speed train to go from Rome to Milan in the north or down to the fabled Amalfi Coast, you should keep two things in mind.
The variety and amount of attractions and experiences on offer in major cities like Rome or Florence is so dense that even a jam-packed whirlwind tour of each is both hectic and shallow. Moreover, you’ll be spending far more time on travel than the length of just the high-speed rail trip. You have to pack, get to the station, find your bearings, and check into new accommodations on arrival, etc. The more places you plan to visit, the more time you’ll end up wasting on logistics.
The fix: Pick one or two cities to explore thoroughly that will double as hubs from which you can explore the neighboring countryside. Build your itinerary around fewer must-see sites and meaningful experiences. Make it flexible so that delays, crowds, or closed attractions don’t trip you up.
Booking Mistakes
Whether it’s the flight, your accommodations, or the attractions you need to book in advance, the most common mistakes stem from a wrong approach to cost savings and booking too early.
Going for the cheapest flight or Airbnb can backfire. It doesn’t make sense to plan for a Roman itinerary and then land in Naples since you’ll end up losing time and money to get the trip back on track. Similarly, paying less for your stay might end up being more expensive if everything worth seeing is farther away.
Committing before you’ve finalized your itinerary is another mistake. Buying non-refundable train tickets or a museum tour that starts at 10 AM sharp in three months without accounting for the weather, delays, or even changes to your travel plans can easily become a waste.
The fix: Paying more can sometimes bring peace of mind. A flexible train ticket or reservation means you won’t have to rush and can experience things at your own pace.
That said, wanting to save money is perfectly valid; you should just go about it in a different way. For example, you can use the best VPN Reddit users recommend when booking accommodation or flights, so that you can get better deals based on different locations and currency. Or, go during the shoulder season to pay even less while also avoiding the crowds.
Packing for Instagram, Not Italy
Travel influencers would have you believe that trips to Italy are all about coupling cute outfits with breathtaking scenery. In reality, you’ll want to leave those high heels at home, because you’ll spend A LOT of time walking between places. Many city centers are also cobbled, so the less luggage you bring, the less rattled you’ll be, literally.
The fix: Pack a practical, light wardrobe with pieces you can mix and match to create more outfits with less. A pair of sturdy walking shoes is a must, as is some more modest attire that covers shoulders and knees you may need to wear when visiting churches.
Relying Only on Public Wi-Fi
While it’s true that most cafes, trattorias, and hotels in Italy offer Wi-Fi as a matter of course, that doesn’t mean you’ll have the internet each time you really need it. Navigating train and local transport schedules, maps, translation, banking, check-ins, etc., all require immediate and reliable internet access.
The fix: Always have an alternative way of going online. Roaming works but can become expensive pretty quickly. Italy eSIMs make more sense since their data plans are often more generous and cheaper than roaming costs. They’re also more convenient than physical SIMs since you can keep your number and use the same local mobile networks for internet access without having to swap anything out.
Renting a Car without a Plan
Parts of Italy like Sicily or rural Tuscany where public transport isn’t as convenient are great for road-trippers. However, renting a car if you stick only to major urban areas might not be a good idea.
On the one hand, public transport is well developed and can get you where you need to go. On the other, many cities have so-called ZTLs or zones of limited traffic. Entering one with a car might cost you a fine and sour the trip.
The fix: Carefully consider before renting a car in Rome, Venice, or Florence. If you do rent, account for the ZTLs and leave car travel only for portions of the trip where it actually helps.