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Northern Italy Itinerary (Milan, Florence, Venice, Lake Como)

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I will be visiting Northern Italy September 2016 for 12 nights. I will be flying in and out of Milan. The places I would like to include during my visit are:
Milan
Lake Como
Cinque Terra
Venice
Florence
If time permits a quaint village in the Tuscany area ( I have visited Cortona & Montepulciano during a previous visit)

I am looking for advice on how many nights in each area along with hotel recommendations (budget $200/night) in well located areas for walking to the sites. Restaurant recommendations too.

Any suggestions for day trips or tours from any of these areas?

Should we travel by train or rent a car OR a combination of the two.

Aside from the "must see" attractions/museums. We prefer to soak up the culture and beauty of small towns vs. city life. We are not shoppers either. Any recommendations will be gratefully received.

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