Five years is a reasonable amount of time for planning a move to Italy and there are two things that you need to do. First, you need to learn to speak Italian as fluently as possible or you will have a very hard time navigating Italian society. Keep in mind that visiting a country as a tourist and actually living there (finding a place to live, a job, etc.) are two very different things. I say this not to discourage you but to introduce a little reality into your planning. Second, you should devote a lot of serious thought to how you will support yourself here. Even highly-educated Italians find this to be a very tough job market and you have to bring some skill with you that makes you valuable or find a way to support yourself without finding a job locally.

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