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I sort of think most of the estates in this region have some trees and produce olive oil though maybe not in commercial quantities, for example castello di Gargonza in the s. part of the Chianti zon did, and I bought some when I stayed there. Maybe if you are staying in the country, your hosts can direct you to a good local source. Too, local product is often available in town shops, if you are looking simply to buy and not to see the operation.
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re: ekc
Poggio Etrusco is the home of Pamela Sheldon Johns who is a cookbook author and does cooking lessons there as well as runs a B&B on her property. it is a beautiful place (was there this past July). Her olive oil is very good, but although she grows and harvests the olives on her property, she does not press the olive oil on premises. If you are looking for the experience to see where the oil is made this may not be the place... there are many wineries that also produce Olive oil in the Montalcino area.
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Badia al Coltibuono is certainly an option, although it may be a little further from Siena than you like.
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re: ekc
Here is a place near Montepulciano, which also may be a little too far for you.
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