As with any plan. Its important to figure out where to get accurate information. We will start right here with an excellent reference.
For those seeking to move to Italy as a retirement plan, as we do, the area of focus is on getting an Elective Residence Visa. To do so you will require (abbreviated description).
1. A Trip to an Italian Consulate in the US
2. Various personal documentation
3. Proof that you can meet minimum income requirements. (I do not list a hard figure as this has been reported as being a floating number depending on which consulate you go to.)
4. Proof of a place to live. Either a rental contract, or property purchase contract. (Yes, you have to set up your place to live before you can get permission to live there. It seems that they are not keen to have you wander about aimlessly.)
5. Proof of medical coverage meeting certain minimum requirements. (No medicare will not cover you outside of the US)
The link in this post is to an excellent all around resource on the rules, forms, ect.