It started with Italy.
That’s it. Just Italy.
My daughter, Allie, and I had been talking about—and saving for—her graduation trip for years. Literally, years. Somewhere along the way, she landed on Italy as the place she wanted to go.
Originally, this was going to be a family trip for all four of us.
There was just one small problem.
My husband, Bill, wasn’t exactly enthusiastic about Italy.
Apparently, the promise of walking all day, climbing endless stairs, and looking at ancient ruins wasn’t quite the sales pitch I thought it was.
So Allie and I started joking:
“Well, if you guys don’t go, the two of us can go twice as long!”
At first, it really was a joke.
Then my son decided he wanted to join the high school fishing club. There was just one rather expensive requirement: they needed a boat.
And that’s how our family travel fund took a very unexpected turn.
We split it.
The boys got a boat. Allie and I got the trip of a lifetime.
Fair trade, if you ask me.
And Then the Trip Went Completely Off the Rails
Have you ever read one of those books where you give an animal one little thing and suddenly you’re 37 steps removed from where you started?
That’s basically what happened with this trip.
It started innocently enough.
Well… if we’re flying all the way to Italy and our flight connects through London anyway, we might as well stay in London for a couple of nights.
Obviously.
Then:
If we’re already in London, Paris is only a short train ride away…
So naturally, we should go to Paris.
And then I discovered the Bernina Express.
Have you seen this train?! It goes through the Swiss Alps! We could take the train through Switzerland and into Italy instead of flying!
Add Switzerland.
But then there was another problem.
I’d already been to England, France, and Switzerland, and I really wanted to visit at least one country I’d never been to before.
What about Amsterdam?
Sure! Add the Netherlands.
Except if we’re taking the train to Amsterdam, we’re going through Brussels anyway…
So shouldn’t we just get off the train, explore Brussels, and stay the night? It would break up the trip!
Add Belgium.
You can probably see where this is going.
One country became two.
Two became four.
Four became five.
And before we knew it, our little graduation trip to Italy had somehow evolved into a six-week European extravaganza.
There were just two teeny-tiny problems with that plan:
We couldn’t afford it.
And…
I have a job.
So… How Much Time Could I Actually Get Off Work?
About eight months before we planned to leave, I decided it was time to talk to my boss.
I figured the worst thing they could do was say no.
So I went big.
I asked for three weeks off.
And honestly?
I completely expected them to say no.
Instead…
They said yes.
I was shocked.
Suddenly, this crazy trip we’d been dreaming about might actually happen.
In the end, though, I decided not to take the full three weeks. We already had another family trip planned for the end of July, and I would need time off for that too.
So I started playing what can only be described as PTO Tetris.
I requested 10 PTO days—essentially two workweeks.
But I strategically scheduled those days around:
- three company holidays
- six weekend days
- and my 10 vacation days
And somehow…
10 PTO days turned into 19 days in Europe.
Now that felt like an accomplishment.
And, frankly, 19 days was probably a blessing in disguise because our budget wasn’t going to survive six weeks in Europe anyway.
The Beginning of the Real Plan
Now we finally knew how much time we had.
19 days.
We knew two other things for certain:
We were going to fly into London.
And we were going to fly home from Rome.
Everything in between?
Completely up for discussion.
By then, our original “graduation trip to Italy” had already become something much bigger. We had London, Paris, Amsterdam, Brussels, and Switzerland floating around the itinerary—and Italy was still supposed to be the whole point.
We had 19 days.
A finite budget.
Two backpacks.
Online maps.
And absolutely no intention of being reasonable.
Now we just had to figure out how many countries we could squeeze in between London and Rome without completely losing our minds.
Spoiler alert: the answer was eight.
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