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Rent a car at the airport or take a train closer to destination then rent?

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In July, DH and I are going to Tuscany for our 20th anniversary. We'll be spending a week just outside of Montalcino, then friends will be joining us for a second week near Cortona.

We haven't booked our flights yet, so there's lots of flexibility. We'll likely fly from Toronto non-stop to Rome, although we'll see how prices fluctuate in the next month or so. I don't have any concerns in principle with the idea of renting a car in Rome, then driving to Montalcino, but I'm wondering if it would be more pleasant and/or less expensive to take a train from Rome to somewhere closer to our destination (perhaps Grosseto or Montepulciano?), and pick up our rental there?

As always, many thanks in advance to the ever helpful Fodorites!

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