I'll be going to Tuscany in October for 3 days and I need help on planning my itinerary. I'd like to be based out of San Gimingano and I'd like to visit some nearby towns. I was thinking Montepulciano, Pienza, or Montalcino. What are your thoughts? I'd like to explore the countryside, towns and shops. I will be renting a car. Also, is it to far to drive to Cortona for 1 day and drive back? Thank you!
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