Italy Is Always a Good Idea
- Anita Simmons
- Aug 1, 2023
- 7 min read
On loss, leaving, learning to be alone and why sometimes the best thing you can do for yourself is buy the ticket.

There are moments in life when you need a vacation.
And then there are moments when you need to pack a suitcase, cross an ocean and temporarily pretend your problems cannot clear customs.
I was somewhere around the latter.
Seven bosses in seven years. A surprise $20,000 special assessment on my townhome. And, far more devastating than either of those things, the loss of two deeply beloved pets.
Life hadn't exactly fallen apart. That would almost have been easier to explain.
Instead, it had worn me down.
Little by little. Change by change. Loss by loss.
I was tired in that particular way sleep doesn't fix.
So, naturally, I went to Italy.
Because if you're going to have an existential crisis, you might as well have it somewhere with excellent carbohydrates.
Why Italy?
Italy wasn't new to me.
I'd already wandered the streets of Rome, fallen for Florence, taken the obligatory photo in Pisa, explored Riomaggiore and the Cinque Terre, navigated Milan and Venice, and made my way through Capri, Naples and Positano.
I'd seen Italy. But I hadn't lived Italy. There's a difference.
A weeklong vacation is an affair. You dress up for each other. You make reservations. You see the highlights. You take beautiful pictures and go home before either of you has time to become annoying.
An extended stay is a relationship.
You learn which café makes your cappuccino exactly the way you like it. You stop looking at Google Maps every five minutes. You discover neighborhoods that aren't on anyone's "10 Things You Must Do" list. You grocery shop. You do laundry. You get lost.
You start recognizing people.
And eventually, wonderfully, you stop feeling like you're visiting. I wanted that.
But first, I needed to learn enough Italian to at least embarrass myself respectfully.
So I spent three months taking Italian language lessons.
Then I packed my bags and left.
No grand life plan.
No dramatic declaration that I was going abroad to "find myself."
Just a woman who had experienced a little too much life in too little time and knew, instinctively, that she needed to go somewhere else for a while.
Preferably somewhere that could intrigue me while keeping my cappuccino cup full.
Or perhaps my coppa di gelato.
The Luxury of Not Knowing Anyone
There is something wonderfully strange about traveling alone.
At home, we are surrounded by identifiers.
Your job. Your house. Your relationships. Your responsibilities. Your calendar. The people who need something from you. The people who know your history.
Then you land in another country where absolutely no one knows who you are.
It's terrifying. And freeing.
You eat when you're hungry. Walk until your feet hurt. Sit at a café for entirely too long because there's nowhere else you're required to be.
You don't have to ask anyone what they want to do next. You simply ask yourself.
It turns out that can be a surprisingly difficult question.
What do I want?
Not what makes sense.
Not what I should do.
Not what someone else needs from me.
What do I want to do today?
Maybe that's the real soul-searching part of solo travel.
Not standing dramatically on a Tuscan hillside waiting for the universe to deliver your life's purpose.
Just learning to listen to yourself again.
Florence, Slowly

Florence had always been one of those places I loved.
But this time, I got to know her. I had time.
Time to wander without an itinerary. Time to cross the Arno simply because I felt like seeing what was on the other side. Time to notice doors and windows and old men talking with their hands.
Time for another cappuccino. Not after noon.
Florence became less about checking off the Duomo and David and more about the rhythm of being there.
That's the gift of staying somewhere longer.
Eventually you stop sightseeing and start seeing.
You notice laundry hanging from windows. The woman opening her shop in the morning.
The sound of dishes coming from a restaurant before dinner service. The way the city changes when the day-trippers disappear.
You realize ordinary life can be beautiful too.
Maybe especially ordinary life.
Lake Como and the Art of Sitting Still

Then there was Lake Como.
Italy has a slightly unfair number of places that make you wonder why you've spent your life living anywhere else, and Lake Como is certainly one of them.
The mountains. The villas. The water. Boats moving slowly across the lake as though even they understand there's no reason to hurry.
I think that's one of the things Italy was beginning to teach me.
I didn't always need to be going somewhere. I could just be somewhere.
That's harder than it sounds when you've spent years measuring your life by productivity, projects, deadlines and whatever crisis happens to be sitting at the top of your inbox.
Sitting beside a lake doesn't accomplish much.
And perhaps that's precisely the point.

Cinque Terre, Genoa and Changing the Plan
I returned to Cinque Terre, a place I'd already loved.
But extended travel has a funny way of changing plans.
One place turns into another. A train ride becomes an idea. An idea becomes another destination.
Cinque Terre turned into Genoa although not exactly by choice.
After becoming seriously ill in 103-degree heat, the 89 steep stairs between me and my room suddenly felt less like charming Italian character and more like a personal attack. I knew I couldn't keep doing it. So I traded my picturesque Cinque Terre hideaway for a hotel in Genoa with one very important amenity: air conditioning.
It wasn't part of the plan. Genoa wasn't even supposed to be part of the trip.
That's another lesson I carried home with me: not everything needs to go according to plan to turn out beautifully.
Sometimes the detour is the trip.
There is freedom in realizing you can change your mind.
Stay another night.
Leave early.
Take the train.
Skip the attraction.
Order dessert. Especially order dessert.
Milan and 120,000 New Friends

By the time I reached Milan, I had gotten pretty good at being alone.
I could navigate the trains, eat dinner by myself, wander a new neighborhood without an agenda and generally figure things out as I went. But Milan gave me something I wasn't expecting from a solo trip.
It reminded me how incredible it feels to be surrounded by people.
I went to see Coldplay at San Siro Stadium. Technically, I went alone. But it's difficult to feel alone when you're singing at the top of your lungs with 120,000 new friends.

There are experiences you enjoy, experiences you remember and then there are those rare moments that somehow become part of you. That night was one of them.
The lights. The music. The entire stadium singing together. Thousands upon thousands of glowing wristbands turning San Siro into something that felt less like a concert and more like its own little universe. I had always loved Coldplay, but that night gave me a deeper connection to their music that has stayed with me ever since.
And maybe there was something particularly meaningful about experiencing it during this trip.
I had gone to Italy because I needed space. I needed quiet. I needed time alone to process what the previous few years had taken out of me.
Then, somewhere in the middle of all that solitude, I found myself standing in a stadium in Milan surrounded by 120,000 people, feeling more alive and connected than I had in a very long time.
And then I changed my hair.

Because apparently that's what women do when we're really ready to start healing.
Somewhere between heartbreak, reinvention and deciding we're going to be just fine, we find ourselves sitting in a salon chair saying some version of, "Let's do something different." (aka Facciamo un cambiamento.)
So I did.
It wasn't some dramatic declaration of a new me. I wasn't trying to become someone else.
Maybe I just needed the woman looking back at me in the mirror to look a little different from the woman who had arrived in Italy carrying all that heaviness.
Hair grows back. Life moves forward. And sometimes a seemingly superficial change on the outside gives us permission to acknowledge that something on the inside is changing too.
That's the funny thing about traveling alone.
You leave thinking the journey will be about learning how to be by yourself.
Instead, you find connection in a stadium full of strangers. You find courage in navigating a city where you don't speak the language particularly well. You find perspective over a cappuccino. And, occasionally, you find a little healing in a Milanese hair salon.
Eat, Pray, Love. Or Whatever You Want to Call It.
There's a reason stories about women leaving their lives temporarily to travel resonate with us.
Call it Eat, Pray, Love.
Call it soul-searching.
Call it running away.
Call it chicken soup for the soul with a side of focaccia.
I don't particularly care what we call it.
I just think sometimes we need it.
We spend so much of adulthood being responsible.
We build careers. Pay mortgages. Maintain relationships. Take care of people and pets.
Meet deadlines. Answer emails.
And then another one.
And another one.
We become incredibly good at carrying things.
Until one day we realize we're tired of carrying everything.
Travel doesn't magically fix grief.
Italy didn't bring my pets back. It didn't erase the professional frustration of seven bosses in seven years. It certainly didn't make that $20,000 HOA assessment disappear.
But it gave me space around those things.
Space to grieve.
Space to think.
Space to breathe.
Space to remember that my life was much larger than whatever happened to be going wrong inside it.
That's an important distinction.
Buy the Ticket
I came home with photographs, stories, a slightly improved Italian vocabulary and very strong opinions about how a cappuccino should be made.
But I brought something else home too.
Perspective.
There is a whole world happening outside whatever little corner of life currently feels overwhelming.
People are drinking espresso at a counter in Florence.
Boats are crossing Lake Como.
Laundry is blowing from windows in Genoa.
Someone in Milan is having an aperitivo with a friend.
Life keeps moving.
And sometimes, when yours feels stuck, you need to go see that for yourself.
You don't have to go to Italy.
You don't have to leave for months.
You don't have to be going through a crisis.
But I do think every woman should, at least once, go somewhere alone.
Have dinner alone.
Get lost alone.
Figure it out alone.
Sit somewhere beautiful with absolutely nowhere else she needs to be.
Ask herself what she wants.
And wait long enough to hear the answer.
As for me?
When life gets a little too loud, I still find myself thinking about Italy.
Maybe it's the architecture.
Maybe it's the people.
Maybe it's the pace of life.
Maybe it's the pasta.
It's probably the pasta.
But I suspect it's something deeper.
Italy reminds me of a version of myself who packed a suitcase when she was tired, crossed an ocean and discovered that being alone and being lonely are two very different things.
She didn't find all the answers.
She didn't need to.
She simply found herself again.
And sometimes, that's enough.
Italy is always a good idea.





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