You're already in Italy, as far as access to affordable tubular tires is concerned.

For the kind of riding you've planned, I'd get some Tufo S33 Pro's for about $40 each.
Very durable, long-lasting tire. Use the mounting tape, for a no-mess, easy install.
That experience alone may well answer any questions you have.

Your bike shop wants to sell you wheels and tires, and then, tires, and tires, and tires.

I see no evidence, anywhere, that flats are guaranteed on tubulars. I've not flatted one.
Enjoy the Olmo. It's not broken, so don't fix it. Get a new tubular tire and ride.

This is very simple. If you see George Clooney riding around Lake Como, say hi.
Let him buy new wheels and tires, and you can stick with what's worked for years and years.