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Where to stay in Italy

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Dear Fodor members, I stumbled upon this site by accident and found a lot of useful information in the forum for our upcoming first time trip to Italy for 3 weeks in December (14th to jan3rd). We are family of four(two kids 15 and 20)
We will be flying in and out of Milan. We will rent a car and plan to drive around everywhere.
This is our planned itinerary
Arrive Milan and drive and stay in Verona(visit como, lakes, Milan) - 3 days
Drive close to Venice and stay - 2 days
Drive to Siena and stay for - 7 days ( do day trips to Florence, Pisa, Tuscany, Gubbio, Montepuciano
Drive to Rome and stay -4 days
Drive back to Milan stay 1 night and fly out.

The Idea is we don't want to be checking in and out of the hotels all the time and would like to stay in a place accessible and drive around. When we try booking hotels we don't know the area we should be looking for.
I appreciate any feedback from members about our itinerary or suggestions (area/ hotels) about our trip. Thank you very much.

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