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Driving from Siena to Florence -- Places to Stop on the Way?

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I will be driving from Siena to the Florence in mid-September. Have the full day to explore the route. Plan on taking the N222 through the Chianti region. If I were to pick a couple of places to stop on the way what you recommend? There appear to be many nice towns....Castellina, Radda, Greve? I suspect there are many smaller villages that offer great vistas or perhaps a great drive off N222 that I may not have seen reviewing other posts. Lastly, interested in any vineyards along the way for a stop as well. Thank you.

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