We are planning to drive through Florence to Naples through the Tuscan countryside leaving early morning with stops in Siena, Montepulciano and Ovieto and the overnighting in Grottaferrata before continuing on the next morning to Naples to drop off the car. The route takes SR2 most of the way except between Montepulciano and Ovieto where it only really makes sense to drive SS71 between them and then back to SR2 to get to Rome and beyond. You can make the trip in 4 hours but that would put us on the major highways which doesn't seem as interesting.
We are renting from Hertz and should have a Ford Galaxy or similar car. The Hertz rental is down the street from where we are staying in Florence (Hertz Via Borgo Ognissanti), From what I can tell from Google maps I will be in a ZTL but will have to go through a ZTL to exit the city. Hertz should call in the current ZTL so I wont get charged for it. Would they call in the second one too since I have to pass through it to leave Florence?
We are overnighting in Grottaferrata to avoid going through Rome. The entire drive is supposed to take about 6 hours total through the countryside so that gives us about 2 hours in each city to get us to Grottaferrata in time for dinner. Each leg is about 1.5 hours so the drive is broken up nicely.
We are doing a private tour of Greve, Castellina and San Gimignano with a driver the day before so I can drink that day. Will we see much of anything different during the drive down past Rome to make it worth it? Or do we see the same countryside in the private tour and just train from Florence to Naples? Part of me wants to drive just to experience it but I also don't want to waste a whole day. I have read about Siena, Montepulciano, and Orvieto which sound amazing. I am also concerned about having to park outside each of the cities and leaving our luggage far away in the car. Do we cover it with something to make sure it's not visible?
Thoughts, comments, changes, what would you recommend? Thanks in advance!