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Siena, Chianti or suggestions for area in Tuscany

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My husband and I (both 26) are planning to visit Tuscany next year (probably early June, 4 nights) and I can't resist the early planning. So...we're looking for an area to stay in Tuscany that will allow us the following:

- Access to wine tours for a day without too much added travel
- Quick access to a few small hill towns, preferably ones not overrun with tourists
- Access to a cooking class (seems easily had just about anywhere)

As for the towns, we don't have any specific interests, we just want towns with some charm or personality that we can roam around in for an afternoon or evening. (Florence isn't a factor as we'll spend time there first.) Our main interest is just enjoying the scenery. Aside from the things mentioned above, I plan to sit in a chair with a glass of Chianti and enjoy a nice view. Maybe we'd be so adventurous as to drive around and view the hills a bit before returning to said chair.

We've been looking at the Chianti area or just south of Siena. Suggestions? More specific place within those areas? Other ideas? Recommended small towns to visit? Extra points if you recommend an agroturismo that provides amazing dinners!

Thanks in advance!

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