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italy and driving

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I'm planning my first trip to Italy, probably in september or october. I want to cover Venice and points west, florence and the surrounding area, ending in rome.
So far, it looks like 20-25 days and I wan to hit a lot of towns like Pisa, Milan, Turin, Bologna, Siena, Verona, Asissi, and some more.
We're not exactly hiking fools so we'd like to be able to do them in a leisurely fashion.

My first inclination is to land in Venice and rent a car but maybe I should wait train it west touching on the towns thru Turin while based in Venice and then rent a car for the trip down to Florence and Rome. Also looking to do San Marino if it makes sense. So, does this make sense?

Also, I'm hoping to rent an apartment in each of the three big cities for about a week each. Anything wrong with this?

We'd be flying out of Rome to return to the states.

Any and all suggestions appreciated

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