Our first stop was at Castello Vicchiomaggio. It's on a hill adjacent to Castello Verrazzano (where we had intended to go first). We arrived a little early so our driver suggested to stop here while we waited for Verrazzano to open. Vecchiomaggio is also a winery but as I mentioned, it was early in the day so we did not do a tasting.
Our next stop was Verrazzano where we took a tour of the castle, tasted the wine, tasted the olive oil and balsamic vinegar but you can read all about that in the Verrazzano post.
After that we headed over to Montagliari, this winery was actually closed but our driver has a good relationship with the owners, so he actually has a key to the place. Our driver suggested buying wine here, because it would be a surefire sign that we went to Italy - try finding Montagliari sold anywhere in the states! He gave us a tour of the cellars and gave us a tasting of basically everything they produced! We tried several different Chiantis including Classico and Reserva, Grappa, Herbed Grappa, 30 and 60 year old Balsamics and many infused olive oils. We ended up buying a bottle or two of wine to bring home and a bottle of Grappa as a gift (this was our Driver's favorite grappa)!
Our next stop was Vescine, we again toured the cellars and did a tasting. Although they were open to the public it seemed like a private tour and tasting because we were the only ones there! Their tasting was unique because they had some white wines as well (we prefer red but if offered free wine why not try it?). Their white wines are produced there but are made from grapes they grow in northern Italy, not at the site we visited in Chianti. We were impressed by their whites, but still, we bought a bottle of Chianti!
What would have been our last stop, was at a winery that our driver told us was one of the biggest wine producers in Chianti, Rocca Delle Macie. For being such a large producer it still felt very personal and again we were the only ones there. Like everywhere else the wine was great! Our favorite wine here was actually a Syrah blend with Sangiovese. Syrah might be our favroite varietal, and we have had a lot of luck with Syrah used as a blending grape as well. Of course, we bought a bottle of it!
When we finished our "last" winery, our driver was so awesome and attentive to our love for wine that he took us to one more winery, Casa Emma. Here we got to try a large selection of wines; they seemed to just keep bringing out more to try. We would have bought a bottle, but we were running out of room in our suitcase. Needless to say the whole day was amazing and I would repeat it again in a heartbeat! How often do you get to go off the beaten path with a local, trying amazing wine with breathtaking views?