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Help me narrow down (if possible) my Tuscan towns.

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I'll have 5 days between landing in Florence, Oct 16th and meeting a group at FCO around noon, Oct 21st. I'm planning a day to see the main sights in Florence and then use it as a base. I'd like to see Volterra, San Gimignano, Assisi and I'd like to see the Siena Duomo floors as they are revealed while I'm there.
Is it possible to do both small hill towns in one day? Then a day trip to Assisi and an overnight stop in Siena on my way to Rome? And still see Florence??
What makes the most sense?

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