Ok I had to do it....
I put in all the cities on the sign in Google Maps
then asked for directions

Then I realized it had to be between Certaldo and Baccaiano

Which low and behold that took me to: Montespertoli, Tuscany

Then using the little man I dropped him on the intersection that made sense and I found this sign.

Notice even the lines on the white sign at the bottom are the same which was in TravelHat's hint

I guess being a old USCG Navigator in a seaplane forced me to keep drawing lines until they all intersected...