After all of my research, I had my heart set on Alessandro Cammilli, a private driver with stellar reviews and what seemed to be cheaper rates! Luckily he still had one day available while we were in Florence/Tuscany, so I eagerly booked him up. His rates really depend on how many people there are in your group. We paid €300 total, which was cheaper than most, if not all, organized tours, and we ended up going to a bunch of wineries (where we most certainly needed a driver by the end of the day - could not have driven ourselves!) and stopped at 5 or 6 hill towns. Really, you can't find a better deal out there!
After our first couple of wineries, we stopped in the very small village of Montefioralle, very close to our next stop of Greve In Chianti. We wondered literally the whole village in probably 10 minutes. Our driver just dropped us off and waited, like he did with all of the other towns. Even though he's just a driver, he's full of knowledge - you don't even need an official tour guide when you have Alessandro! He told us to keep an eye out for the home of Amerigo Vespucci, an Italian explorer from the 1400s-1500s.
Next we stopped in the town of Greve In Chianti, perhaps the most well known of the hill towns of the Chianti region. Here, there is basically a large piazza in the center of town. Shops and restaurants line the square. We walked around and stopped in a few shops in probably 20 minutes. My biggest draw of Greve was a wine shop, Le Cantine di Greve in Chianti, where you get a prepaid card and then use it to try over 140 wines, most of which are local. We ended up not going here, because we went to a mini version down the street where we tried some food too, but more on that in another post.
In the next town, Panzano In Chianti, we ate lunch at Mac Dario and looked at the amazing views.
Radda is one of the typical hill towns of Tuscany. We wandered through the town in less than 10 minutes.
The next town, Castellina In Chianti, was definitely my favorite of the hill towns. It's most notable feature is an underground passage that was used in the town's defense back in medieval times. Now it is lined with shops and art galleries. Wandering the passage just felt really cool, and the town in general was the most picturesque of any of the hill towns.