Which would be safer bet? Should I rent a car outside of Rome and drive to Greve or take the train to Florence and rent a car once I arrive? I plan on spending 3 days in Tuscany/Chianti and from what I have read it seems driving this portion of the trip would allow the most freedom. Thanks
Many people opt to train to either Orvieto or Chiusi to pick up the car. Smaller towns, easy train connections from Rome and points beyond, less hassle with ZTls in Florence and not as far to go as all the way to Florence.
I agree with either starting in Rome (although drive is not too interesting until you get to Tuscany or with previous poster who suggested train to someplace like Orvieto and then going touring from there. Either option is probably easier than Florence. Rome is much easier to drive out of from airport than from more central rental offices.