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Questions for a Once in a lifetime trip to Italy

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I have been waiting my whole life to go to Italy! My husband finally told me to start investigating possibilities of where to stay. Since I'm sure this will be my only trip to Europe, (money and age) I want to make the best of it. I would love to get opinions on places to stay and the time of year to go. I'm thinking October, I don't want it to be too hot or too cold. I would like jeans and sweater weather. I would love a centrally located lcharming little apartment or villa, close to a train station so we can explore other "must see" places. I don't want a real touristy area but would love to be close to charming little (Mom and Pop) restaurants. Since there are so many places in Italy I want to see, I'm not sure if it would be better to rent one place for three weeks and them move to another location for another three weeks. I'm also open to having one central location and traveling by train somewhere else and staying in a hotel for a couple of days. We love good food and wine. I want to see the sites but i also want to be around the locals and shop at the markets. We had originally thought of doing your typical Italian vacation for the first two weeks, (Rome, Florence, Venice, Amalfi Coast) and then renting a place for a month. I'm curious to hear from those of you that have been, if you could do it over again, what would you do. My places of interest to rent are below. But since I have never been, I'm hoping for some friendly input.
Umbria
Perugia
Luca
Manitoba
Orvieto
Portofino
Sorrento
Florence
But, I am open for suggestions. Garzie

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