I chose to take a big leap and moved to Italia -- just me and my terrific dog, Jake. It is not a simple thing -- nothing like "Under the Tuscan Sun". You must obtain a visa in order to be in the country for more than 90 days out of 365. And the police stop people all the time to check your documents.
I was fortunate to receive a long term stay visa D -- no working, no student visa. If you are under 50 the Italians frown on granting you a visa unless you can prove that you have more than enough financial reserves in order to protect Italian jobs. Orvieto was my choice for a home base and it was perfect. I rented an apartment on line and arrived without knowing a soul, didn't speak the language (but I did speak Spanish and passable French) and had really no clue what to expect. There is a lot of beauracratic red tape (you must visit 5 different government offices and none are open on the same day so if you start out of order you will be wasting a lot of time).
The 18 months in Italia were amazing. I never felt unsafe (well, except once when I took a wrong turn in the bad neighborhoods in Napoli), and because I had a cute dog with me, I never felt alone. Italians (and many Europeans) have their priorities and their values straight. Family first. Not money. Not a new car or a bigger house. I was invited countless times to join strangers for Sunday lunch. They were not strangers for long!
I highly recommend the experience and I'm looking forward to formally retiring in Italia -- much more affordable there than in the States. Their health care is excellent, the cost of housing and other essentials is far less than the US, and the food/wine/surroundings are superb! I highly recommend having a car -- being able to jump in the car and head out to explore the backroads was a big part of why I loved my experience so much.
If you have questions, let me know. Orvieto is a wonderful place to live and is very centrally located. I could have lunch on the Mediterranean (an hour and 15 away), or visit Florence or Rome (about an hour and a half away), and it was about 4 hours to get to Lake Como or Sirolo (on the Adriatic -- spectacular place).
Caterina e Jake