Has anyone has experienced with renting a car in Italy and driving around and exploring the Southern Tuscany region? What was your experience like? How intimidating was it, or was it something a newbie can pick up relatively quickly? I've always wanted to see the iconic landscape of Southern Tuscany, and I understand that you really need our own transportation to see the area. I've never driven overseas before and only drive automatic. Let say I'm able to get an automatic rental and it has a GPS. How hard would it be to pick up the car from Florence's airport and drive to the Tuscany town of Pienza, for example. I've read that streets in Italy don't have numbers on them, just the name of the city that you're approaching.


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! Be aware that the navigation system doesn't work in some areas, like Siena. But, driving in Tuscany is not difficult if you are comfortable on narrow, windy roads. Stay off the autostrada if you want to see the scenery. The drive from Florence to Siena is beautiful. Stop in Greve, Monteriggioni (it is a tiny fortress, hill town that has changed very little in hundreds of years), San Gimignano. If you want to do a wine tasting go to Dievole. They do a wonderful tour and tasting, paired with some foods. You can also stay there, it's a bed and breakfast.