Let’s talk about the first trip I ever booked truly on my own. Not just a little quick trip back home to see my family, but the first big international trip I planned entirely by myself.
It was well over 30 years ago, and I had decided to attempt to plan my own travels through Italy.
If you’re doing the math, “over 30 years ago” means pre-internet, pre-home computers, pre-Google-search days — basically prehistoric times.
Back then, if you wanted to plan a trip, you had two choices: go sit in a travel agent’s office and discuss your travel needs with an actual human being, or buy a really good travel guide and read through it to figure out where you wanted to go.
For my first excursion to Europe, I chose the latter.
This was a huge mistake.
The biggest problem was that I couldn’t really visualize the geography of a place just by reading about it. More importantly, I had absolutely no concept of how long it would take to get from Point A to Point B.
If I’m being fair to my younger self, this particular travel skill took me quite a while to master. I’m very good at it now, but it took a couple of miserable failures to get there.
And this was one of them.
I decided we would land at Da Vinci Airport in Rome, rent a car, and then drive around Italy at will — which, by the way, I would never do again – public transport is just too good.
But there we were, hopping into our little Europcar rental and boldly heading north toward Siena.
Hey, I’m in Italy! Not a care in the world.
Now, on a map, the journey from Rome to Siena looks like a quick two-hour drive. We landed in Rome around 2:00 p.m., and after clearing immigration and picking up the car, we were on the road by about 3:30.
We should have no trouble getting there by dusk, right?
Easy? You bet.
Relaxing? How could it not be?
With our ultimate destination being Florence the following day, we would have all kinds of time to stop and explore the beautiful Tuscan countryside. Maybe we’d even have a nice glass of Chianti later that night.
Glorious!
Except that it wasn’t.
The first issue was that, at the time, I knew almost nothing about Italy beyond Rome, Venice, and maybe a bit of Pompeii.
(This is where my future blog about researching the history and geography of places before you go becomes extremely relevant.)
The second thing was that I had never even considered how hilly that part of Italy would be.
Never. Even. Considered.
So there I was, excitedly flipping through page after page of magical destinations in my guidebook, when I discovered a remote little place called Chiusdino.
I decided this would be a fantastic place to spend my first night in Italy.
Chiusdino.
The first issue was that, at the time, I knew almost nothing about Italy beyond Rome, Venice, and maybe a bit of Pompeii.
(This is where my future blog about researching the history and geography of places before you go becomes extremely relevant.)
The second thing was that I had never even considered how hilly that part of Italy would be.
Never. Even. Considered.
So there I was, excitedly flipping through page after page of magical destinations in my guidebook, when I discovered a remote little place called Chiusdino.
I decided this would be a fantastic place to spend my first night in Italy.
Chiusdino.
Ever heard of it?
No?
Hm. Strange.
Actually, I’m now fairly convinced that unless you were born and raised there, nobody has.
Most people landing in Rome for their first trip to Italy might choose to stay in Rome. Perhaps at a reputable, well-known hotel. Hilton? Marriott? Hyatt?
Nope.
Not me.
Let’s pick a tiny B&B in Chiusdino.
That’s a good idea!
Because why be “most people” when you can be daring, curious, bold, and hopefully come home with fantastical stories from your dream European excursion?
And technically, I did.
Just not the kind I was expecting.
You see, guidebooks use words like “charming”, “whimsical”, and “medieval.”
I apparently stopped reading before I got to the part about “perched on a hilltop overlooking the valley.”
Because choosing Chiusdino was essentially the equivalent of planning a nice vacation in Los Angeles and deciding to pop up to Big Bear for the night.
Of course, being the planner that I am, I had already paid for the lodging. It wasn’t a fortune — maybe 200,000 lire, which was roughly $100 at the time — but I had paid for it. So onward we went.
Up the hill.
Around the bend.
Down the other side.
Up another hill.
A deer here.
A fox there.
No idea where we were.
No idea.
And what I had imagined would be an easy little two-hour drive through the Tuscan countryside eventually amounted to almost four hours.
By the time we finally arrived, it was dark.
Very dark.
In the tiny village of Chiusdino, there was no sightseeing.
There was no exploring.
There were no happy tales of leisurely wandering through the Tuscan countryside.
There was, however, wine.
And a lovely family who greeted two exhausted, slightly lost Americans with a welcoming smile.
And maybe that’s the part of the story worth remembering.
I’ve learned a lot from those early travel mistakes, and one thing I’ve discovered over the years is that the farther you venture from the main tourist areas, the nicer the people often are, the more beautiful the scenery becomes, and the wilder the stories you’ll have to remember your travels by.
Would I stay in Chiusdino again?
No.
Not a chance.
But I’m very glad I did it once.
And I lived to tell the tale.
