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Advice for Milan - best place to pick up rental car?

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We will be driving from Milan to Castellina (Tuscany), we're keeping the car for 5 days and then dropping it off in Florence (maybe the airport?). I'm trying to figure out what location to rent from in Milan. We will be staying at Hotel Berna and it looks like there is a Hertz location very near the hotel at Via Cappellini 10 but I'm worried that driving out of the city from there will be difficult.

Would picking it up from one of the airports be better? Any help is appreciated!

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