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Tuscany Help!

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My husband & I are interested in spending a few days in Siena after a 3 day trip to Florence this coming May. Here is what I am thinking (suggestions/recommendations are greatly appreciated!!): Arrive in Siena by bus or train in the mid afternoon (I believe it's roughly an hour travel time from Florence). sightsee around Siena and have a nice dinner. 2nd day- travel by either private driver or tour to San Gimignano and Montegriggioni. I've seen some links to "take me out to Tuscany" and she seems very flexible with creating a private tour for you- not sure of the cost. From what I have looked up the two towns are only about 44 minutes away so it seems like an easy day trip. I would like to visit some wineries/vineyards especially in the chianti region. I have heard Tenuta Torciano in SG is amazing.
3rd day- spend the day exploring Siena. Leave late afternoon/early evening for Rome. Any recommendations on restaurants/museums, etc?

Does this seem achievable?

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