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3 weeks in Italy...questions...

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My husband and I are planning a 3 week trip to Italy in October 2017, considering flying into Milan, exploring northern areas a bit (Lake Como, Piedmont, then over to Venice, then Cinque Terre, working our way from north to south, Naples), then flying out of Rome at the end of our trip. We'd love to experience spending time in wine country, perhaps an agrotourismo experience, and perhaps more rural than city. Our style is wanting to spend more time (3 nights) in great, centralized places rather then do a frenzied pace to get to lots of places.
Questions: How much time should we dedicate to Cinque Terre? Is Florence/Tuscany similar to Umbria? Are there any areas we should consider hiring drivers vs. taking trains? Anyone have good suggestions for great lodging places? We are budget conscious but want safe and clean, of course. Thank you.

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