I live in Austria, and we brought our UK registered car with us, so I have first hand experience. Here, you have to register your car within one month if you are registered as having your main home here - and you have to go that within days of arrival.
There are people from the UK here who run UK registered cars for extended periods, but it's illegal. If the tax police (yes, they do have such things here) catch up with you, you'll have to pay all the ongoing excise duty due since you arrived, plus the import duty, plus a penalty of several times the import duty. The import duty here is based on the value of the car and the emissions.
Obviously it may not be the same in Italy, but it was no problem re-registering the car and insuring it locally once it had the appropriate paperwork.
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