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Itinerary help

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My husband and I are going to Italy next September and would like some help with the itinerary I have planned. Any advice would be appreciated.
fly from Rome to Venice - 3 days
train to Florence - 3 days
train to CT - 2 days
train to Siena 3 days
4 days of car travel in Tuscany/Umbria -Pienza, Montepulciano, Montalcino
Rome -3 days

My main questions are: would you go from Venice to Florence or CT first?
Where would you rent a car from? We want to avoid driving into any cities and want to drop the car off at the same place as pickup to avoid the heavy charges.
San Gimignano - would you make the trip from Florence/Siena or rent your car staring there?
CT - I am really confused which village to pick

I would appreciate any and all advice

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