Napalm’s advice on making sure about import details is well-said. Search this forum and the other one, there’s a lot of information out there.
My father-in-law picked up a BMW 5-Series from the factory in Munich in 1992, and took it on a six week European family vacation before importing it back to the US, and still drives it to this day.
If you haven’t done so before, driving and also parking in European cities is not for the faint-hearted, including Italy (I really don’t recommend driving in Rome). Driving in the countryside is lovely of course, and probably more comfortable with a RRC than Defender.
Other than import issues, I’d be worried about mechanical issues on a car that may have been sitting for a long while; but that somewhat depends on your mechanical ability and whether you speak Italian / have local family or friends that could help you out.