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Rental car to Greve n Chianti

My wife and I are traveling to Italy for 10 days at the end of Sept./beginning of Oct. We fly into Naples, stay 3 days in Sorrent then on to Greve in Chianti (4 days) and end our trip flying out if Rome. I have never driven in Italy but would like to have a rental car for our 4 days @ a B&B in Chianti. Is it better to rent a car and drive from Naples or rent a car from either Siena or Florence? I have heard that it is difficult to pick up and drop off a rental in Florence ( we will be taking a train from Tuscany to Rome after using the rental). Any advice would be appreciated. Thanks

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I just posted this response to a similar question: We rented a car in Florence to drive into and around Tuscany and just got it from Budget. It was located in the city, so it was "interesting" to get out of the city and will test your navigational skills but it was cheaper to get it there than the airport, though the airport is probably easier for driving. We went ahead and drove it into Rome and dropped off near the Borghese Gallery. It wasn't too far into the really hectic part of the city and seemed no crazier than driving out of Florence. Same thing here it was cheaper to drop here than the airport or train station, so we took our chances with the traffic. We also looked into dropping in Orvieto, but it was more expensive (at least for our timing)and the days/hours of operation were much more restrictive. We also looked at Avis, which was right near Budget, but Budget was cheaper at the time. It's also cheaper to do this than return back to Florence and then buy two train tickets, and then of can hit more southern towns along the way.