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Northern Italy and Tuscany-Are we crazy?

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My husband and I have decided that we want to take a trip to Italy in September, only one month away. We would like to see the Dolomites area, Lake Como (Bellagio), maybe Asti/Alba, Cinque Terre, Lucca and Siena. We will drive. Arrival/departure airports are yet to be decided, whatever is best I guess (maybe into Milan, out of Florence). My main questions: are we going to to be able to book hotels at this late date or will they all be full? how many days would you recommend for this? We are looking to experience more of the country's natural beauty although we will throw in some churches and art here and there. Any recommendations for a route?

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