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Wine tour in Chianti

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Walks of Italy, which was recommended by someone here, is not available on the date in May end for a wine tour in the chianti area. Does anyone have a personal experience of another tour which is recommended? The idea is to go to a wine estate for some sampling and lunch and cover one town to get a feel (San gimignano or Siena).
We are 3 adults with one 4 yr old. Would you rather recommend hiring a driver with car to take us around for 7/8 hours. This would give us more flexibility I guess. Any reco here for car / driver hire would be appreciated.

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