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Train & Car Rental Logistics from Florence

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My husband and I are taking a train to Florence from Venice this July, and I'd appreciate help with the car rental logistics from there!

We're not staying in Florence, but instead are only picking up a rental car to head to Tuscany (we're staying in an agriturismo near San Gimignano).

I've read that the rental car situation near the Florence train station is chaotic, to say the least, and people have recommended cabbing to the airport to rent our car from there instead of renting near the station. We did get a rental car from the Florence airport several years ago for a different Tuscany trip, and that seemed to go smoothly enough, but I was just wondering if it makes more sense to find a rental company south of the train station instead of north. We're heading south to San Gimignano, so why go northwest to the airport? If we do cab to the airport, what should we expect the fare to be?

The other option I've seen suggested is to take the train to a further city and rent the car from there, thereby skipping the Florence driving hassle at all. My concern in this case would be whether we would have to change trains in Florence from the one we arrived on from Venice. If we can just stay on that first train, what town would be simply "next" on that line? (And then we'd need to see if this next destination is a shorter or longer drive from our accommodations than Florence would be!)

We'll be leaving Florence by train again at the end of our Tuscan adventure to head further south.

Also, could you confirm that this is the best place to buy train tickets for Italy in general? There seem to be a few different options!
https://www.italiarail.com/

Thanks to everyone in advance!

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