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Single woman 40's 1st time traveling to Italy

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I'm wanting to travel to Italy alone. I'm a 40 something year old female.
And have never been to Europe. What's the best time of year to go? I'm starting to do my research now. But I don't want to get too OCD about it. I'd like to go within the next 6 months maybe even Fall and it's July right now.
I'm currently living in Florida so I love warm weather. I want to be able to do this on the cheap, perhaps even 3 months or so. I want to take my time, taking in the culture, sights, fashion, maybe if I enjoy it enough to take up permanent residence. I really don't know any Italian, however I'm street smart and not naive when it comes to pick-pockets, scammers, etc, so I'd like to stay in more of where all the action is.
How difficult/easy is it to get a work visa? Where do I start? Any direction would be helpful.

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