Retiring to Italy

I suggest you start out on Wikipedia reading about the Schengen Agreement. You don't say where you're from, however U.S. citizens have to get a visa to stay in most of the E.U. for more than 90 days out of 180 days.
And the visa's are very difficult to get unless you're a college student. Most retirees are not students.

It can be done but it is tedious. You must apply for a resident visa (in the US or your country of residence), provide proof of medical insurance, financial stability, have a lease on a place to live in Italy, and other requirements.

Laurel, who lives in Roma, can give you advice. The website to start with, I think, is the Italian Consulate near you.

There's also a retiringtoitaly.it, seemingly answering all questions from those who are starting the consider the possibility. I skimmed through some of the sections and it seems like it carries very reliable information.

I would start with the website suggested, you can also search for the term "expat", while that will bring up many more sites for other than retirement, it will open up some discussion boards and other help type resources.

While it is a process, and long term (years) is different than an extended visa; as residency is different than visiting, it can be worth the effort. As someone said, students have it relatively easy, and while it can be very difficult for working age people to get any extended visa, it does get easier for retirees, especially if you have the financial resources. Countries like people living there, spending money, but are not a drain on social resources.

One website you may want to bookmark is the following:
http://www.transitionsabroad.com

You can filter by country - in your case, Italy - as well as gain an understanding of what's entailed for medical, housing, economies of scale within a given region, etc. While not 'retirement planning' specific, there are articles about retiring overseas within the various tabs. Hope this helps!

Hi. I sent you a PM with some info. Have you spent much time in Italy as a traveler? Do you know where you want to live?

As to medical care, you need to have private insurance as you will not qualify for the national insurance plan for some time. Medicare does not cover you outside of the U.S. The care itself is high quality, in my opinion.

I don't know if sguastaferri is your last name or a nick name, but if it's your last name you could qualify for Italian citizenship if you are a descendant of an Italian citizen.
If you can obtain citizenship that way (and many descendants of Italian immigrants have), you can go to Italy without visa requirements or financial means tests. You would also qualify for coverage by the Servizio Sanitario Nazionale (National Health Service), if you establish residency in Italy (residency, not just citizenship, is required for SSN coverage).
Some information here from my local Italian Consulate.
http://www.conssanfrancisco.esteri.it/consolato_sanfrancisco/en/i_servizi/per_i_cittadini/cittadinanza/citizenship-by-descent.html