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Hill Towns of Tuscany, Which to Choose?

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My wife and I will be staying in agroturismo in Monteroni d'Ariba for three nights from September 29 to October 2.

Prior to my arrival, we will have already visited Florence, Montereggioni and San Gimingano. We plan on spending a full day (most likely September 30) in Siena. But what do the following day??

We will have a car, so we have many options but can't decide: Chiante, Monutepulciano, Arezzo, Perugia, Cortona?

Any advice on which to visit or if there are other I may be neglecting?

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