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Lake Como & Tuscany

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My husband and I are planning our first trip to Italy. We plan to go late Sept/early Oct of next year (2015). We want to take a direct flight from the States so we'll be flying into either Milan or Venice and spending 10 to 12 days in Italy. Our destinations are Lake Como and Tuscany. I thought we could start in Lake Como and spend a few days there and then head to Tuscany. I plan to get a hotel in Florence and spend a few days there & take a day trip to Pisa. I thought we would then head south into the Tuscan countryside and tour some wineries and have a cooking class. I'd like to find a central location to stay while we're in this area. We were thinking of having a private tour guide for the Tuscan area but I haven't really found any guides that don't start at the boat docks or Rome so I think we'll be on our own. How does this sound as a starting point for my planning? Accepting any and all suggestions :)

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