Three Factors That Can Ruin Your Italy Trip + What I Do

December 20, 2025

So often, I hear and read about the disappointment of travelers about their trip to Italy. Whether it’s because they didn’t manage to see as much as they wanted, they didn’t find what they were expecting, or they ended up spending more than they had previously planned.

After decades of traveling around the world, I know full well that traveling involves surprises, culture shocks, and being caught off guard, especially when you are out of your comfort zone.

But there are a few tricks I suggest my clients adopt to minimize the impact, and a few things I do when I plan their itineraries or complete tours.

Image: Santa Maria Sopra Minerva Basilica in Rome suggested by Angela Corrias travel designer and Italy specialist.

Problem 1 – You want to see everything

Let me just be straightforward: unless you are visiting a small town with one or two landmarks, it’s impossible to see everything.

I’ve been living in Rome for almost thirty years. Guess what? I didn’t see everything. The same applies to Florence, Venice, Naples, and many other cities and regions.

Also, define everything. Is it every museum? Every monument? Every church?

The bigger the city, the more difficult it is to visit every place of interest.

For example, I often receive requests for custom itineraries in Sardinia where clients ask to visit the whole island in five days. Now, Sardinia is actually an island, but it’s not a small one like the Elba or the Maddalena archipelago islands can be. It’s in fact a big region and one of the largest islands in Italy, second only to Sicily by less than 2,000 square meters!

How to solve it

My suggestion here is to read, research, check out distances, consider how many places there are to visit, and how many you actually want to include in your travel plan.

Most of all, consider how much time you have in the destination and what type of holiday you want.

Do you want to relax and enjoy some rest time, or are you looking for a landmark marathon?

Do you want to focus on nature or culture? Archaeology or food?

The very first step I take when I’m hired to help travelers plan their trips is to arrange a Zoom call where I ask all sorts of questions about their travel style, pace, and priorities.

Once I have sorted out what kind of holiday the client wants, I start my research.

Because I know the city so well, for me, crafting custom Rome itineraries requires less research than a multi-city or even multi-region plan. But generally speaking, matching and combining schedules and availability is quite the job.

Problem 2 – Cost-related surprises come up

The highest impacting factor on the costs you should expect is your travel style. If you stay in 5-star hotels and eat at Michelin-starred restaurants, your expenses will be higher than those of travelers who book a room in a B&B and eat street food.

Both travel styles are fine, as long as you know what you will be paying without having last-minute surprises!

Image: Angela Corrias ravel advisor and Italy specialist suggests checking restaurant prices to avoid surprises.

How to solve it

The solution for unwanted cost surprises is two-fold: when you are planning and when you are traveling.

During the planning stage, I suggest booking as much as possible. While it’s not easy to book every single restaurant, you can (and should) book your hotels and transport, whether it’s train, plane, or rental car.

Even if you are not booking every single monument, you can still see their entrance fee and have a good idea of what you are going to spend on sightseeing.

When you are traveling, so already in Italy, most of the surprises might come from eating out and shopping. In both cases, my suggestion is to check the prices before you purchase or enter a bar or restaurant.

Usually, restaurants have their menu displayed outside with all the prices visible and so do bars with their price list either outside or hanging on the wall inside. The same applies to gelato shops, where you have the price list for all the options of scoops and cones/cups, and obviously, also the stores selling clothes, shoes, and accessories, where all the prices are shown by law.

Problem 3 – You don’t consider travel time

I reckon Italy is not a huge country, but traveling from one city to another takes time, whether you are taking the train, driving, or flying.

As a matter of fact, sometimes traveling by train is less time-consuming because you would go from city center to city center without having to reach the airport, usually far from the town.

Nevertheless, sometimes, getting from one place to another can take you half a day, so it’s crucial that you take this into consideration when planning your day, because you might also want to include some resting time, plan your meals, and organize your sightseeing accordingly.

How to solve it

Give your travel time the same importance as your sightseeing, if not more! Ah logistics! You love it or hate it, but how it’s organized can really make or break your holiday!

What I suggest is to start looking at the different transfers you need to do right after you craft a skeleton itinerary and you adjust as you move forward with your planning.

If logistics really bores you, fret not! I can craft your itinerary and organize a full vacation package with everything booked and sorted out. Explore my tailor-made Italy tour package services for more information and arrange a complimentary inquiry call.

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Image: Angela Corrias travel designer and writer.

About The Author: Angela Corrias

Sardinia-made and Rome-based travel designer and writer specialized in Italy.

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