In some cases you could fly just outside Italy.
For example if you land at Portoroz or Ljubljana (Slovenia) it is just a bus into NE Italy.
Slovenia is infinitely better organised and more GA friendly than Italy has ever been (with certain exceptions like Trieste but there you have the hassle of the avgas pump at the end of the long narrow taxiway).
One could also land anywhere along the Croatian coast (Pula, Losinj, Brac, Split, Dubrovnik - all superbly friendly and organised airports with avgas and customs) and take a relatively short boat to any of the ports on the E Italian coast.
The problem with Italy, and most of the other countries down that way, is that the way things work there is that the locals will find "ways" around it but a visitor is going to be easy prey, especially if he can't speak Italian.