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Tuscany-which region for day trips

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Hello-Our vacation will be late June to early July. First time in Tuscany.

We will be flying into Pisa then taking a train immediately to Florence for 2 days. We will then be renting a car and driving from Florence. This is where I am unsure what comes next. What Is the best home base for day trips to SIena, Volterra and San Gimignano? We have identified our two options: San Casciano in Val Di Pesa (Salvadonica) or Montalcino (Castello Banfi). We will spend 5 nights in either place and then drive back to Pisa for one overnight returning home after that. So, a total of 9 travel days. This is a very special birthday for me and the husband and I will be taking our two teens-ages 14 and 17. We do love wine-thus the choice of locations but I don't want this to be the decision on location (which grape region). Any input would be great! Thank you!

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