6 Reasons Your Italy Trip Turned into a Disaster (+ How to Fix It)

You’ve been dreaming of Italy for a long time and you are excited that you are finally getting there. Then you get here and your trip doesn’t turn out how you would actually expected and wished for.

What happened?

What could you have done differently?

Here are a few reasons why your Italy trip turned into a disaster (and how to fix it).

Image: Crowded season one of the reasons why your Italy trip turned into a disaster.

You followed the crowds (literally)

So many times have I heard tourists complain about crowds in Rome, Florence, Venice, Cinque Terre, and the Amalfi Coast. But this is hardly surprising since most tourists keep insisting on going only to the major tourist hubs in the highest season.

If you keep thinking like the crowds, you will keep being part of the same crowds you don’t want to see.

Solution: Prefer low and shoulder season and stray away from larger cities and tourist destinations. Italy has twenty beautiful regions, each of them holding history to be discovered, dishes to be savored, nature to be explored, and art to be admired.

Image: Angela Corrias of Fearlessly Italy in Portovenere when visiting Cinque Terre.

You didn’t plan ahead

The idea of last-minute trips conveys this romantic vibe of wild adventure, but in reality, it often results in trips gone wrong.

In my opinion, only very experienced travelers, travel agents, and tour operators can afford to go on holiday without planning much of it. Why? Because they have probably planned so much for clients that they know schedules and addresses by heart.

“Civilians”? They should plan to make sure the hotels they like have availability, the flights are not too expensive, the landmarks they want to visit are not sold out.

Solution: Start planning between nine months and one year ahead if you are coming from outside Europe.

You hired the wrong travel agent/consultant

It’s sad to hear travelers dropped by travel agents or trips gone wrong because of misleading information and bad organization. But this is what happens when a travel agent doesn’t know Italy, has either never been or only once or twice.

Just because “Italy sells”, it doesn’t mean that one can instantly be an Italy travel expert.

Solution: Prefer travel agents and advisors who have taken their time to visit Italy, to see the landmarks they include in their itineraries, to try the restaurants they suggest, to experience Italy beyond cruising Venice canals on a gondola.

📍 Need help in planning your trip or a full, detailed itinerary? Choose between my Italy travel planning services or custom itineraries tailored to YOUR needs and passions.

Image: Angela Corrias travel advisor exploring offbeat Italy.

You didn’t do your research

From disappointing restaurants to closed monuments, a lack of research can ruin any trip. In Italy, this takes the shape of standing in long lines because you didn’t know you could buy your ticket online, overspending and eating in tourist traps, but especially missing out on regional culture and traditions.

By not paying attention to detailed research, you might end up visiting Rome in July. School holidays, I get it, believe me, I have a son in school, but Rome and Florence in summer are unbearably hot and walking around incredibly difficult.

Getting your facts straight during the planning process will probably lead you to fresher summer destinations thankfully Italy doesn’t lack in.

Solution: Do you want to plan your trip on your own? Great! But make sure your sources are reliable and up-to-date.

Image: Angela Corrias travel advisor and designer in Rome, Italy.

You scrolled too much on Instagram

Between randomly-sourced information and AI-generated images, Instagram reels often create a misleading hype resulting in disappointed travelers.

If you see empty Spanish Steps in full daylight on a bright day, you can safely assume it’s a fake because such a central and popular landmark in Rome is always crowded. As a matter of fact, I found it quite empty in winter at 4 am.

Solution: Do you like Instagram? Great! Follow accounts of Italian travel content creators, local administrations (Rome has one very active), and official profiles of places you want to visit.

You asked ChatGPT!

Don’t even get me started at the tips and itineraries created by ChatGPT. Nonsense routes, impossible tips, closed restaurants, just to begin with.

But letting aside the practical tips that AI can get right or wrong and let’s suppose it gives you some correct piece of advice.

Is AI going to understand YOU and YOUR interests?

Is AI going to convey the feel of a first-hand experience in a place?

Is AI going to ask you if everything is going/went well during your vacation?

AI might be free, but so is the quality of AI travel planning.

Solution: Ask a human travel planner/advisor!

Check out here all my travel planning services and pick the right one for you!

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Angela Corrias, journalist travel writer in Italy in the fall.

About The Author: Angela Corrias

Hi, I’m Angela Corrias, an Italian journalist and travel writer with over a decade of experience exploring my beautiful country. Through FearlesslyItaly.com, I share my favorite places — from iconic landmarks to hidden gems — to help you plan your dream trip to Italy. My work, specially Italy travel guides has been featured in Forbes, National Geographic, and Lonely Planet. I’m here to make your Italian adventure unforgettable!

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