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Rental Car from Northern Italy - Tuscany - Rome

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We leave soon for a two-week Italian adventure! Planning to use public transit for the first week in Lake Como & the Dolomites, but want a car for 2nd week in Tuscany. My question is about best places to pick up and drop off the car, for most convenience.

Here's our rough schedule, for 3 people:

-leaving Castelrotto (near Bolzano) on a Saturday morning; possible stops in Verona or Pisa en route to our destination near Pienza (Siena Province)

-one week usage in southern Tuscany, exploring hill towns, etc.

-then we fly out of Rome the following Sunday morning (would like to visit Orvieto &/or Civita di Bagnoregio en route on Saturday)

Other considerations:
According to Via Michelin, it's 6-7 hours total drive time from point to point. We've driven in Germany & Italy before; feel that train travel is generally more relaxing since you can sit and look out the window without having to be "on" (directions, Italian drivers, etc). I'd lean towards just taking a train to Florence or somewhere close and then picking up the car, but the train costs to get 3 of us that far are much higher than just picking up our car & driving, since we need it that day anyway to reach our final destination.

Leaning toward picking up rental car in Bolzano or Verona, driving the 6-ish hours to Pienza, then dropping the car in Orvieto the following Saturday after seeing O & Civita; train to Rome city center/train the next morning to Rome airport.

Does this make sense to you intrepid Italy drivers? Any tips on which ar rental locations to use?! Any other considerations to keep in mind? (GPS, maps, rental agencies, free upgrades, etc) Appreciate all input!

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