If you're an American, the first thing to consider is how you'll manage to stay there for "a few months." You are only allowed 90 days unless you manage to procure a long-term visa (being a student might help you with that).

Other than that, sure, why not?

Since I am retired and have a guaranteed income, I think I may be able to stay longer. If not, I'll keep my stay under 90 days.

If you can find a solution to your visa issue (though to be granted a long-stay visa as an American, you need to show proof of long-term accommodation, a bit of Catch-22 situation!), another problem is other than holiday rentals (which are quite expensive and unrealistic for long residence), most conventional rentals in Italy are for several years, often four. While it's possible to terminate early after giving sufficient notice, it's not ideal and not very flexible. Also while many landlords are happy to rent their property for several months in low season, in peak summer months (and winter in Alpine area), they want to charge and expect top whack per week. For example, it may be 200 euro per week in low season but 1000 euro in July and August.
If you read Italian, there are online property search engines, and local rental agents may be able to help. Perhaps the easiest is to find British expat owners.

"Since I am retired and have a guaranteed income, I think I may be able to stay longer. If not, I'll keep my stay under 90 days."

It isn't that simple - just being retired and having income. So do it the easy way and stay 3 months or less.

But possibly a better option would be to first enroll in an approved school and get your visa through them. You could go on a student visa - but arrangements must be made in advance.

I wish you well in your efforts. Please don't be tempted to stay illegally. I'm not sure how easy it would be for you to get a long stay visa. You need to contact the Italian embassy asap about that.
A student visa normally only covers the period you are actually registered with a recognised school.

Renting a holiday home may be possible in off or shoulder season, but would be very expensive in the peak season, and may not be possible - some will already have bookings for the coming summer.

Do make sure you have health insurance to cover your entire stay, including if you want it evacuation insurance. Certainly if you are staying longer than 90 days normal travel insurance will not cover you. Of course your own insurance may already cover you but you need to check, and the conditions they apply.

Why not pick 3 locations for a month each---that will work.

If you enroll in language schools, meeting al the legal requirements to stay will be simple. Even if you don't enroll in a language school. if you can document to the Italian government that you have enough money you don't need to work and have your own health insurance, a long-term stay in Italy is what a LOT OF PEOPLE DO. There are many non-EU citizens living in Italy for the majority of the year.

However, if you want to see a lot of Italy from a "base", it is better to pick a place with good train connections elsewhere rather than rely on having a car. Le Marche does not have good train connections. Tuscany does, and not all of it is expensive. There are many landlords in Pistoia, Certaldo, San Miniato, Impruneta, Chiusi, Prato Montecatini, Pietrasanta, Camaiore, Orbetello -- and on and on in Tuscany -- who would be delighted to cut you a deal for a long-term rental.

You might also consider Emilia-Romagna for good train connections, and the Veneto and Liguria. Italian cities are expensive when it comes to rentals. Small towns are not. It can be very affordable to be in a village and occasionally rely on taxis to take you to the train station for excursions.

There are interesting, certified language schools all over Italy.

Be aware that a lot of discouragement you will get is based on pure jealousy and other people's failures to take the risks to do what they wanted to do (move to Europe). Many, many, many people who are not EU citizens live in Europe as retirees, students, or tourists on long-term stays.

http://jonesesavenezia.blogspot.it/

http://www.ft.com/intl/cms/s/2/cc4d1632-477d-11e1-b646-00144feabdc0.html#axzz2DwOOCRMC

<<Be aware that a lot of discouragement you will get is based on pure jealousy and other people's failures to take the risks to do what they wanted to do (move to Europe).>>

Just where, exactly, are you finding the "discouragement" or "jealousy" or "other people's failures" in this thread? People are offering practical advice about looking into visa issues (something anyone who wants to go trotting off to Europe for extended periods needs to do). I don't see anything but helpful advice. As to whether "A LOT OF PEOPLE" up and move to Italy for long stays, well, duh...a lot of them skirt the law, too, or are ignorant of it. Who would want to be among them?

The requirements from the Italian embassy are here: http://www.expatsinitaly.com/node/19

If you want to be granted a long-term visa on the basis of being a student, you must be in classes at least 80 hours a month.

I've been looking into apartment rentals for awhile. The suggestion above about looking in small town/villages may be a good idea I haven't tried. But, what I've concluded after looking at Rome, Florence, Venice, is we can probably get B&B accomodations (with breakfast) for about the same price...and have the advantage of a local host and his/her advice on where/what/when/etc and perhaps some laundry facilities...without the hassle. And we can go city/location to location and stay the time we wish without traveling back to a home base. There is a language school in Todi that I've read about...and they also arrange day trips. Anyway...good luck. PS...I think 90 days will be plenty. Be sure to go to the lake district...dolomites... We've been studying Italian about 18 months with a tutor (native of Turin). I'd suggest you find someone local to give you the fundamentals befor you go. It's "different."

If you are retired, have a guaranteed income and can demonstrate that you have full medical insurance for the length of your stay (and medicare does not cover you outside the US) then you can apply to the nearest Italian embassy or consulate - but do allow plenty of time to do the paperwork and receive approval (as in months) for a residential visa.

I would contact them as soon as possible so you can find out what the requirements are.

As for the usual length of rental - sorry, this is beyond my experience.

There is no one place to base that would be geographically and logistically ideal for exploring the entire country. So, if your goal/hope is to see as much of the country as possible, I would do as bobthenavigator suggests and rent in three different places for one month each. Or even move every three weeks.

The folks above are giving you good advice. One thing I would stress would be to not rent a long term apartment until you have been in country for at least a month. You might not like the first place you stay, the town might not be the right one for you, the school not to your taste, etc. Go for a short term apartment at first, and you will probably get good advice when in country as to the perfect long term place for you to settle.

Thanks to all of you for your responses! Many great suggestions already. I like the idea of staying a month in three different places. I really want to experience the flavor of the country, and not simply see the main tourist attractions. In fact, I would love to be able to stay with a family for a couple of weeks (I think it can be arranged through the language school?) as it would give me a better glimpse into how people actually live. Also some practice speaking the language.

I am so glad I found this forum!

You could pick a school in a small town that arranged family stays or most also arrange for private apartments. Rent a car for day trips. You can get a leased car cheaper than a rental (must be at least 17 days), but you have to pick up and return at airports in Italy. Il Sasso language school in Montepulciano might be a good option if you wanted to rent a car.

http://www.ilsasso.com/eng/

You could do some trips by train/bus from Solemar Sicilia language school in Cefalu, Sicily.

http://www.solemar-sicilia.it/en/

Both schools have reviews on Fodor's.

You're getting good advice here. A very long term solution would be to apply through your consulate for elective residency. But it sounds like for now you might want to just stay for the 90 days. If you want to return, you can start the process once you get back home.

You can arrange your accommodations through most language schools for the duration of your tuition, and then a possibility, if you like the place, is to approach the landlord and ask if you can extend your rental. Otherwise, if you like the town, you'll be there and can start asking around, much easier to do in person than long distance.

Don't get too excited about the idea of staying with a family. While some people have great experiences, it's often just someone who takes on boarders in their spare room as a way to make extra cash. You might barely talk with them or see them. And the way they live? Pretty much like you do

merrydith- It's not crazy at all. I am a single female in my mid-50's and I just submitted my application for an Italian "Elective Residence" visa yesterday.

Unlike poster who stated it would be "months", the Italian consulate where I went stated that visas were taking about one week to process. Now, it may be longer if you have to go to a busier consulate, but I would guess 2-3 weeks at most. You should check the website for the Italian Consulate for your State. The website will usually list what the current waiting times are for visa applications. Here is the first page that asks relevant questions re your visa request: http://www.esteri.it/visti/home_eng.asp

I do not know yet if they are going to grant me the visa; but they accepted my application, my backup documentation and the visa fee. I am cautiously optimistic.

While I understand (through much research) that the approval process may be completely ambiguous with regards to "requirements" being met, you should go for it, if it is what you desire.

I also understand that once I've received the visa, I must apply for a residency permit immediately upon arrival in Italy. And that the residency permit might take 3 months to receive.

Additionally, I will be required to prove (every 6 months) that I still meet the requirements for the visa (i.e. health insurance, monthly minimum income of E3000 or so, and a bank balance that exceeds 70 or 80k, and proof of housing).

Buona fortuna, merrydith!