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Recommendations for a Drive through Chianti

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Part of my trip next year to Italy will include a day driving through Chianti from Florence en route to our place outside of San Gimignano. We want to stop in a few towns and sites along the way and are looking for suggestions. We are interested in history, small towns, food, and wine.

We are hoping to get to our hotel around 3:00 to check in, relax for about an hour, before heading to San Gimignano for evening exploring and dinner (about a 10 minute drive from our place).

The drive looks like it will take about 2 and a half hours max, and we will be on the road no later than 10:30, which leaves us about 2 hours of exploring time, and part of this will be for lunch. What about two of the following towns? Maybe lunch and a quick stroll in one of the larger ones (Greve or Panzano) and some quick exploring in one or two of the small ones (Radda, Castellini, or Montefioralle)?

Let me know what you think would be best, and if I am missing anything. Thanks!

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