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Advice on Tuscan hilltowns itinerary

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I will be in Italy for 2 weeks in early October and I am seeking advice on an itinerary for our time spent in Tuscany. Our current itinerary has us in Venice for 3 nights, 5 nights in Rome, 4 nights in Tuscany (hilltowns), 1 night in Florence. Should we take one night from Rome and add it to Tuscany?

Which hilltowns do you recommend spending our time in? As of right now, the main places we want to see are Siena, San Gimignano, and Montepulciano. Where else would you recommend, and how would you draft an itinerary? I'm not sure where we are going to stay yet, but we would like to stay in an agriturismo perhaps. We will be renting a car. I've heard that visiting 2 hilltowns per day is recommended, but geography is not my best subject so I'm having trouble figuring out which hilltowns it makes sense to see together based on their location. Can anyone recommend an itinerary for us including which hilltowns to see and what you recommend doing there? I feel like I've read so many different posts/trip reports that the hilltowns all sound the same at this point so I'm having trouble narrowing down the choices!

Thanks!! :)

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