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Need help on Tuscany portion of trip

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My husband and I are taking my first trip to Italy (he went in college) in September. We arrive in Rome on the 19th and plan to head immediately to our first destination. We are flying out of Venice on the 30th and already have a hotel booked there for the 2 nights prior. We plan to be in Florence for 3 nights before that. This leaves us 5 nights at the start of our trip which we are planning to spend in the Tuscan region. The issue is where to base ourselves (one location or two) and which places to try and fit in during that time.

We are not real big into history or art so will probably limit ourselves to just some of the must-sees while we are in Italy. We prefer to experience the beauty of the countryside while also sampling delicious food and wine. We plan to have a car for these 5 days, dropping it off once we arrive in Florence.

We thought about making Sienna our base but are open to something a little smaller and more quaint. I have done a bunch of research but am overwhelmed by all the options. I would love recommendations on how to make the most of these 5 days without running ourselves crazy. Places to stay and must see places to visit would be greatly appreciated.
Thanks.

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