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I am a Canadian citizen, currently living in Italy. My 90-day Schengen visiting period is due to expire in a month. However, I would like to stay for several more months (learn the language and travel around). Is it possible to extend my stay without leaving Italy? Can I apply for a visa for Italy in Italy? If not, can I apply for a residence permit? If I can get a residence permit, will I have problems leaving/entering the country because my Schengen entry stamp will show that I overstayed?

I saw a very good reply here Extended stay visa for Germany Is there a similar, proper process for Italy?

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Long term visas exist in Italy (Visto Nazionale) but I think you need to state a valid reason for staying (like studies, work, etc.). See if Google Translate translates this page well enough for you:

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It may take 30 days to have the visa done anyway, or even 90 if you're a freelance worker.

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Italy now provides an online visa questionnaire (in several languages, including English) that will provide visa instructions based on your nationality, residence, and length and purpose of visit.

For what it's worth, there is currently no visa that would allow a Canadian citizen and resident to stay for longer than 90 days in Italy for the purposes of tourism.

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