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8 Nights in Tuscany

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We are spending 3 weeks in Italy this October to early November. We have dedicated 8 nights of our trip to Tuscany. We are thinking of Florence, Chianti, Siena, and Grosseto. This is our first time to Tuscany and have no idea about location and how easy it is to get to each place via car.
Question: Should we spend a couple nights at different hotels in each place, OR stay at one awesome place centrally and drive to each place?

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