From navigating train strikes to learning why cappuccinos after lunch earn you side-eyes, here are the things I wish someone had told me before I packed my bags and moved to Italy.
When I first decided to move to Italy, I thought I had done my research.
I’d watched countless YouTube videos, read travel blogs, followed Italian influencers on Instagram, and spent years dreaming about strolling through Tuscan vineyards while effortlessly ordering espresso in perfect Italian. I visited religiously, building a community, starting a teaching business, and becoming a regular where it matters.
Then I got here.
And while Italy has been every bit as beautiful, delicious, and inspiring as I imagined, there were also plenty of surprises…some charming, some frustrating, and some that left me standing in a train station wondering what exactly had just happened.
If you’re planning a solo trip to Italy – or thinking about moving here yourselfhere are the things I wish I knew before traveling to Italy alone.
1. Italy Doesn’t Run on Your Schedule
As an American, I was used to convenience.
Need groceries at 10 p.m.? No problem.
Want to grab lunch at 3 p.m.? Easy.
Need customer service immediately? Someone will answer.
Italy has a different relationship with time.
Many small businesses close in the afternoon, restaurants often don’t open for dinner until 7:00 or 7:30 p.m., and things simply happen at a slower pace.
At first, I found this frustrating.
Now? I find it refreshing.
Italy constantly reminds me that life isn’t meant to be rushed.
What I Learned:
Build flexibility into your plans and don’t expect things to operate on an American timeline.
2. Learning Basic Italian Changes Everything
Can you visit Italy without speaking Italian?
Absolutely.
Can you have a much richer experience if you learn some Italian?
Also absolutely.
Even simple phrases like:
- Buongiorno (Good morning)
- Grazie (Thank you)
- Per favore (Please)
- Parla inglese? (Do you speak English?)
go a long way.
People are generally much warmer and more patient when they see you’re making an effort.
Some of my favorite experiences happened because I attempted a conversation in imperfect Italian.
3. Italian Style Is Less About Fashion and More About Effort
Before arriving, I assumed Italians spent fortunes on designer clothing.
The reality?
Most people simply know how to dress well.
You’ll notice:
- Well-fitted clothing
- Neutral colors
- Quality basics
- Comfortable but polished shoes
Meanwhile, Americans often stand out immediately because of oversized athletic wear, college sweatshirts, and flip-flops.
Nobody expects you to look like you’re walking a Milan runway.
But putting a little effort into your appearance goes a long way.
What I Wish I Packed:
- Fewer leggings
- More linen pieces
- A versatile jacket
- Comfortable but stylish walking shoes
4. Dinner Is an Event, Not a Task
One of the biggest culture shocks was how seriously Italians take meals.
In the United States, meals are often squeezed between appointments.
In Italy, meals are the appointment.
Nobody is rushing you out the door.
Nobody is dropping the check five minutes after your plate arrives.
A dinner can easily last two or three hours.
And honestly?
It’s one of my favorite parts of living here.
5. Cappuccino Rules Are Real (Sort Of)
Let’s talk about it.
Yes, Italians generally drink cappuccinos in the morning.
No, the police won’t arrest you if you order one after lunch.
But you may get a slightly amused look.
Once you understand that coffee in Italy is deeply connected to culture and tradition, these little customs start to make sense.
My advice?
Learn the customs, then order whatever makes you happy.
6. Public Transportation Is Amazing—Until It Isn’t
One reason I chose Italy was the ability to travel without owning a car.
The train network is incredible.
I’ve traveled between cities for a fraction of what similar trips would cost in the United States.
But here’s what I didn’t understand:
Train strikes happen.
Often.
Welcome to Italy.
Transportation workers periodically strike, and while many essential services still operate, delays and cancellations are part of life.
What I Wish I Knew:
Always have a backup plan.
And never schedule an important international connection with zero buffer time.
7. Italian Bureaucracy Is an Extreme Sport
Nobody prepared me for the paperwork.
Not the visa paperwork.
Not the residency paperwork.
Not the tax code paperwork.
The paperwork for the paperwork.
As a traveler, you’ll probably avoid most of this.
As a student or expat?
Prepare yourself.
Bring copies of everything.
Then bring copies of those copies.
Then make digital copies too.
You’ll thank me later.
8. Politics Shows Up in Everyday Conversations
Many Americans avoid discussing politics with strangers.
Italy is different.
Politics often comes up naturally during conversations.
From immigration and tourism to labor strikes and regional issues, people are generally more comfortable expressing opinions openly.
My biggest lesson?
Listen more than you talk.
You can learn a lot about a country by understanding what matters to the people who live there.
9. Every Region Feels Like a Different Country
Before moving here, I thought of Italy as one culture.
Now I know it’s dozens of cultures.
The food changes.
The dialects change.
The traditions change.
The architecture changes.
The pace of life changes.
The experience of living in Florence is completely different from living in Naples, Palermo, Bologna, or Milan.
One of the best things you can do is get beyond Rome, Florence, and Venice.
Some of my favorite memories have happened in places most tourists never visit.
10. Solo Travel in Italy Is Easier Than You Think
Before I arrived, I worried about eating alone.
Exploring alone.
Traveling between cities alone.
I worried people would notice.
The truth?
Nobody cares.
Italy taught me that solo travel isn’t lonely.
It’s freedom.
Freedom to linger over a glass of wine.
Freedom to spend four hours in a museum.
Freedom to change your plans because you discovered a tiny village you’ve never heard of.
Some of my most meaningful experiences happened because I was alone and open to them.
11. The “Dolce Vita” Is Real—But Not in the Way You Think
When people imagine Italy, they picture vineyards, sunsets, Vespa rides, and endless pasta.
Those things exist.
But the real Dolce Vita isn’t luxury.
It’s presence.
It’s sitting in a piazza with nowhere to be.
It’s lingering over coffee.
It’s walking home at sunset.
It’s prioritizing relationships over productivity.
Moving here has taught me that a good life isn’t necessarily a busy life.
And honestly, that’s the lesson I didn’t know I needed.
Final Thoughts
Italy is beautiful.
It’s chaotic.
It’s inspiring.
It’s occasionally frustrating.
And it’s one of the most rewarding places I’ve ever traveled.
If you’re planning your first solo trip to Italy, my advice is simple:
Come with an open mind.
Expect things to be different.
Let go of the need to control every detail.
Because the moments you’ll remember most often happen when your plans don’t.
And trust me—that’s where the magic begins.
Have you traveled to Italy solo, or are you planning your first trip? Share your questions and experiences in the comments below—I love connecting with fellow travelers navigating Italy for the first time.
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