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Need advice on a place that is half-way between San Gimignano and Pompeii

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We decided to drop Umbria from our trip and just use San Gimignano as a base for our day trips to Florence, etc. We would like to turn in our car in Sienna and then just take a train to our next stop. Can anyone suggest some good towns as well as hotels for us to stay in? We are looking at about three days before we need to head down to Pompeii. We have a 15 year old daughter.
Thanks!

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