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Florence Day Trips Advice

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I was hoping someone on here could offer up some advice on a few options for day trips from Florence in early October. From what I read on here renting a car is my best bet. I have seen good things about San G and the Chianti region. We are wine lovers so please keep that in mind. One of my concerns is about the rental car. Namely leaving the city from the rental car place and returning it. Has anyone done this in the past and could you help me accomplish this with the least potential for headaches?

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