Common Italy Travel Mistakes (and How to Avoid Them)

Are you dreaming of sipping your first espresso in Rome, marveling at stunning frescoes in Florence’s art, or soaking up the sun on the Amalfi Coast? Italy is waiting for you but don’t let these common trip planning mistakes ruin your Italian adventure!

In this article we’re sharing the top mistakes travelers make when planning their Italy trips plus how to avoid them. There are some simple quick fixes to these issues but it will take a little bit of care and attention to work through them.

If you’re already at the point where you’d like some help to get your trip in order and avoid all the stress, our team of trip planning consultants can help you pull everything together so you can relax and get back to dreaming of that pistachio gelato.

1. Overloading Your Itinerary

We get it. Italy is amazing and there are so many things to see and do. But, when you try to pack everything in, you end up spending your precious vacation time in transit – on a plane, train, checking in and out of hotels. Sure you might see some of the main sites but there’s precious little time for soaking up the atmosphere and living your best dolce vita life – which is actually the best part about traveling in Italy.

The thing is, there is simply no way you can see it all in Italy in one two week trip. Not even the highlights. Even after decades of travel we’re still scratching the surface. So avoid this Italy trip planning mistake and pick a few places to explore and relax into the beautiful adventure that is Italy.

2. Not Understanding Transportation Logistics

Getting around Italy is generally straightforward and there are plenty of options to choose from. Some make more sense than others however and unfortunately popular sites like Google Maps and Rome2Rio do not have all the answers. We learned this the hard way.

As a general rule, if you’re traveling between major cities like Rome and Florence, use the fast speed train services that take you to and from the center of each city. There are no long security lines or checks. You simply turn up and ride the comfortable train.

Driving is great if you want to go more off the beaten path and you’ve understood the costs and logistics involved eg avoiding historic centers, tolls, where to park etc

Flying is really only the best option if you’re visiting the islands of Sicily and Sardinia or you’re traveling a very long distance or to an area that is not served by fast speed rail.

The thing is, in Italy, many local services do not publish their maps and schedules online or in apps so the information you’re looking for is not necessarily easy to access online, let alone in English. Say ciao to the ferries on the Italian lakes – they are definitely in this category.

3. Traveling in Peak Season

If you can manage it, visiting Italy outside of the peak season is always the best idea for lovely weather for sightseeing and slightly smaller crowds.

So when is peak season? For the major tourist areas – Rome, Florence, Venice, Tuscany, the Amalfi Coast and Cinque Terre – the peak season runs early May to end of October. During this time, you’ll experience high prices and bigger crowds. 

Outside the major tourist zones the peak months are generally June to September. And the further you get away from those zones the quieter and less expensive it gets, with more options and value. 

4. Not Researching Public Holidays and Opening Times

In these days of the internet, where we can book anything on a whim in a matter of seconds, it’s easy to forget to check key items of logistics. In Italy there are local customs to be aware of as well as regular closing days. You’ll need to check the places you want to visit. 

In many, if not most, smaller towns and villages throughout Italy, shops will be closed from lunch in the early afternoon and reopen around 4pm. This is traditionally a time to rest and it can be frustrating for those of us who like to be on the go. 

Most historic sights like the Colosseum and Pompeii are free to enter on the last Sunday of each month however while this sounds like a great time to visit, you will be managing huge crowds of locals as well as the usual tourist traffic.

5. Not Understanding Documents Needed

With over 150,000 members in our Italy Travel Planning community we’ve heard and seen it all when it comes to Italy travel mistakes and not getting your documentation in order is one of the most common and easily avoidable issues. 

Most importantly – make sure you have at least 3 months to expiry on your passport after your departure date per Italian law (we prefer 6 months). If you want to rent a car you’ll need your International Driver’s Permit as well as your licence from home. 

6. Doing Minimal Research

These days there are a million gorgeous photos and videos on the internet to inspire your travels. What they don’t show you is the reality of the place you are visiting. Yes Positano (pictured above) is amazing and a beautiful town. It’s also tiny, expensive, crowded and very steep. So while that tantalizing glimpse of a gorgeous coastline with filters applied is appealing, try to take a broader view. 

Would you prefer to be paying many hundreds of dollars for an average room without a view plus dinner with half of Chicago? Or, are you open to a lovely family run hotel with a balcony overlooking the Tyrrhenian Sea at a town that may not have gone viral on Instagram? 

We have hundreds of articles, podcast episodes and our online travel assistant full of practical information to help you with trip planning. Or, if you’d like personalized assistance we also offer trip planning services including complete itinerary planning.

7. Bringing the Wrong Shoes

Italy is a country where getting around on foot is generally your best option when it comes to exploring cities, towns, villages and sights. You’ll easily do up to 15,000 steps a day, probably more. So make sure your feet are comfortable and you have the right shoes. 

Sneakers are fine, so are sandals and flat boots but leave your heels at home unless you’ve been practising walking on cobblestones for months. Apart from the fact that you’ll be slow getting around as you try balance yourself, the potential for a twisted ankle is very high. I too enjoy fashion but I love vacationing in Italy more. 

8. Copying Generic Itineraries

These days it might seem easy to whip together an itinerary using online tools or following a suggestion on social media. Usually these itineraries follow a well worn path so guess what? You’re going to run into many 1000s of other people doing exactly the same thing.

Here at Untold Italy we encourage you to lean into your interests and passions and go out of your way to discover the true magic of regional Italy – the smaller towns and villages where you’ll feel right at home. 

So if you love to cook, take a cooking class that teaches you dishes you’ve always wanted to learn. If you love prestige cars, take a Ferrari for a spin in the town where they are made or if you love hiking, head to the Dolomites for some of the most spectacular walks around. 

Ask yourself, “What do I want from my Italian adventure?” and build your itinerary from there. 

We love helping visitors plan their trips and can’t wait to delve into any challenge thrown at us. Want to discover the dark arts in Turin or find a private shopping experience tailored just to you? We’d love to help. Find out more on our Italy trip planning services page.

The Best Mistake You Can Make in Italy

Now while we’re all for planning, and these days it is necessary to avoid disappointment, often the best travel experiences and stories happen when you’ve made a mistake or got lost or they simply evolve from a quiet moment.

Once we got our rental car stuck between two walls in a small town in Sicily and had to get the manager at the hotel where we were staying to get it out. It wasn’t actually that funny at the time but it is now. The look on the manager’s face was priceless. Clearly I had not read his instructions. Oops.

Another time we went for a stroll after dinner on the Ligurian Coast and bumped into a little concert playing at the bandstand in Santa Margherita Ligure. This was where my daughter (aged 2) got her first kiss. No consent was given but little Giacomo certainly found out about that concept from his mother that day. And then we all became friends.

There is a balance to be found between not enough and too much planning. You’ll know when you hit the sweet spot because those little moments will happen that you just know you’ll be thinking about for years to come.

Some people say it’s a mistake to travel with kids but as you can see from the photo above, we had a fantastic time in Venice. Kids force you to learn how to have a flexible plan and I’ve learned a lot from our two as they continue their adventures in Italy.

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