a longer stay in Italy

First make sure that you check into the requirements for a visa that will allow you to stay that long. The Schengen Agreement limits stays to 90 days in any 180 days without a separate visa. People on a tourist visa are generally not permitted to work.

Contact the Italian liason office in Chicago or the main embassy in DC. If you can demonstrate passive income of at least 15K per year, it is possible. PM for more specifics.

As mentioned, there are formal visas that allow longer stay, but they usually require some additional proof of your travel than just showing up. One might be a student visa, this usually requires paperwork from a US or Italian school showing enrollment and duration of the course. The other would be an extended visa, that may be limited to six months, but usually requires some proof of income, sometimes proof of health insurance, sometimes a "sponsor" or proof of residence. In the end, they want to assure that you are not going there to find work or be a burden to the state, so if you are older or wealthy...better chance; young and poor...little chance unless you are a student. Either way, contact the nearest Embassy or consulate, or start at their website.

I guess re-reading your question, the other option for you would be to find a position before leaving the US. you really can not show up and look for a job, nor can you legally work on an informal basis, charging a fee. You can obtain a position with an Italian firm ahead of time, having them take care of the visa, Or get a position with a US firm that will place you in Italy. Beyond that, you may have others suggest websites for Ex-Pats or agencies that place people in Italy, but can't vouch for any of them.

Thank you all for your input. I definitely have my work cut out for me, but perhaps starting at the embassy might be the best place.

Eileen, I agree, starting at the Embassy is the best way to begin, as they'll be able to provide the most accurate information. On a related note, I had a nice chat with a couple from the U.S. last year in Rome. They had been living there for about six months, and of course my first question was about the Schengen Limit and the paperwork for an extended stay. As you might imagine, the bureaucracy in Italy is extremely complicated, so be prepared to spend several months getting the necessary approvals. As others have mentioned, you'll be required to provide information of your financial assets, to prove that you can live in Italy without employment income. You'll also have to provide your Marriage Certificate and lots of other documents. Although it's more related to those permanently moving to Italy, you may find it interesting to read This Website. Good luck!

Thanks again to you all for you input. I found another website, mentioned in the book Take Your Children to Europe, that looks promising, too. It's called www.transitionsabroad.com You have all helped so much. Maybe this time next year I'll be posting from Italy!!!

Eileen~Please be sure to get a place with extra bedrooms...you WILL be having visitors!!! (hahaha!) Hmmm, I'm envisioning a monthly meeting of the Helpline at your place!

Absolutely!!! We all could munch on pasta and sip wine as we overlook the Arno.... Why not dream big, eh?