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Southern Tuscany

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I have two weeks off in mid May and I'm thinking about spending a few days (up to 1 week) exploring the Southern Tuscany area. I've always wanted to photograph those iconic Tuscany landscape that we always see.

I've never driven overseas before and only drive automatic, so I'm kind of apprehensive about renting a car. I don't mind paying a bit more to rent an automatic though. Will driving in general be an issue in Southern Tuscany?

Where should I based myself? Sienna seems like an ideal place, but I'd be worry about having a place to park each time I drive back into the city.

Is it easy to pull the car off to the side at any time and stop to take pictures?

I think I might want to hire a guide at least for the first day or two to show me some of the most ideal locations and then I can come back to those places later myself. How would I go about finding one or should I just get a map and drive around on my own and hope that I don't get loss :).

Thanks.

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