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Tuscan Vineyards (near Siena)

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My husband and I will be traveling to Italy in May of 2013 for a two week vacation.
We are an early 30's couple who decided to start our trip in Venice, travel to the Tuscan region (wine lovers), Rome, Pompeii/Naples, Sorrento and Capri.
I am in need of guidance for the Tuscany part of our trip. We decided to skip Florence and focus more on the Siena/Chianti region as we wanted to get a feel for the wine country. That being said, we are thinking of making Siena our home base for the 2 days we have allocated coming in from Venice.

What specific vineyards/wineries are close to Siena that you would recommend? We would at least like to see 5. I have been to Napa, so I'm pulling from that experience but I'm open to hearing the differences so I can set my expectations.

We are thinking of hiring a private driver (expensive, but we are weighing the pros & cons) for about an eight hour day. We have looked into the group tours (the bus picks you up at the hotel, two vinyeard visit and a lunch), but something about not having the flexiblility to pick where we want to eat, or when we want to leave is unappealing to me.

Any tips for other "must dos" in the area are greatly appreciated. Thank you!

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