I was wondering if a Cadillac DTS (the big one) is the sort of car that will draw too much attention and get stolen.  I have not been able to find any Cadillac DTS in Italy (online, ebay, etc) so I imagine it is pretty rare. 
Any other experiences or ideas about having a Caddy in Italy would be welcome. 
(I will have a Fiat for daily use!)
 

Well,  Good luck on any repairs here and also fitting it down some of the small streets.  You will get dents and good size scrapes on it.  I have a Mazda CX-9 and it can be a challenge driving, but Mazda does not scream American.  Cadillac does and might get broken into.  On the other hand if you bring it, you might not have any issues.

I got a small Fiat for my daily rider.  So far I haven't seen any Caddys around, except for a few small CTS's.  I guess that they are pretty rare.  I had a friend say that it will either be stolen within a week or no one will ever touch it because they will think it is the mafia's.