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Leave Florence or Day Trip - Logistical Help Please!

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My traveling group of 4 -self, husband and 2 children in their 20's - will be visiting Italy this coming June. We'll be arriving in Florence by train (from Rome) on a Tuesday, and had planned to spend that afternoon and all of the next day, Wednesday, seeing some of the city's main attractions. Our original plans were to leave Florence on Thursday (taxi to car rental on outskirts of city center) and begin our 6 day car exploration of the Tuscan countryside - itinerary still pending but to include San Gimignano, Volterra, Sienna and the area south of Siena.

Our dilemna is this: we have been invited to a dinner back in Florence on Friday night which we would like to attend. Is it realistic to keep to our plans of driving out of Florence on Thursday, staying overnight at a hotel or apartment in the San Gimignano vicinity, doing more sightseeing on Friday (Siena?) and driving back into Florence for dinner on Friday night? (And possibly driving back out again that same night to whatever hotel we're staying at outside of the city.) Would it be more realistic to just keep Florence as our base until Saturday and do day trips? Any input from someone who's done this - including the feasibility of driving and using one of the public parking lots on the outskirts of the city - would be appreciated!

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