You have nine days and have 6 places you want to visit. Let's assume you are arriving and departing from Rome (do you depart on Friday or Saturday?). If it was me I would use my jet-lag day to take the train thru Florence to the Cinque Terre. Then reverse your itinerary....
I personally like Levanto as a base - you haven't mentioned a preference.
Wednesday - arrive Rome, train Rome to Cinque Terre, two nights in CT
Thursday - Cinque Terre
Friday - train to Florence, rent car, go on to Sienna, three nights in Sienna (parking will be an issue).
Saturday - Volterra/San Gimignano
Sunday - Sienna
Monday - Drive to Montepulciano, two nights in Montepulciano
Tuesday - Montepulciano
Wednesday - Drive to Ovieto, two nights in Ovieto
Thursday - tour Civita
Friday - Drive back to Rome
Saturday - depart Rome
Only you can say if this is enough time in each place for you, but I prefer three night stays to enjoy where I am.