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Tuscan Adventure: Seeking Itinerary Advice

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Hi, Everyone! Hoping you can help us out with your expertise. We are going to Italy and Greece In late May/early June for our honeymoon and we're trying to lock down our itinerary. We'll be spending 4 nights in Tuscany following time in Venice and Cinque Terre. I've been to Florence before, so we thought we would focus on seeing and photographing the hill towns and countryside of Tuscany (I'm a photog). We'd like to see a bit of Chianti and a bit more of the Val d' Orcia in the limited time we have. We'll be flying out of Rome on an 11am flight on our last day in Italy.

So my first question is, where would be a good overnight location for the night before our flight from Rome? Do we need to give up one of our nights in Tuscany? We're open to suggestions. Or is Pienza or the Montepulciano area too far from the airport? We looked on google maps and it appears to be about a 2 hour drive? We weren't planning on going into Rome this trip since our time is so limited (bummer!). We were also planning on renting a car for Tuscany and are nervous about to driving into Rome. One more piece of info is that we'd really like to visit Civita di Bagnoregio since we'll be in the area. So does it make sense to spend the last night somewhere closer to Rome, maybe near CdB and take a train from Orvieto to Rome for our flight in the morning? Or is driving from that area to the airport a safer bet instead of relying on the train system? We don't mind getting up early to drive, but since we're not familiar with the roads, we want to make sure we're not trying to go too far and risk missing our flight. Many thanks for your guidance!

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