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Rome to Pitigliano - Sienna - San Gimignano - Florence best way?

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In the middle of our 16 day trip to Italy, we plan to visit Pitigliano, Sienna, San Gimignano and Florence, focusing on some of the Jewish history while we explore Tuscany. We will be leaving from Rome after spending 4 days there. We're planning to stay 1 night in Sienna and 2 nights in Tuscany before going to La Spezia for a night.

Questions: Should we rent a car in Rome and keep it for this leg of the trip, dropping it in Florence? Alternative: Take the train to Orvieto to rent a car, drive to Pitigiano and drop it in Sienna, taking busses and trains for the rest of the journey. I've heard that the drive out of Rome is horrendous and that there's lots of car theft, leaving the car outside Sienna. If the alternative, how would we get to San Gimignano and from there to Florence? Also, any ideas on how to arrange a tour of a Kosher winery in the area? Thanks!

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