Robert, I don’t have Michael’s vast expertise, but I’ve been to the Chianti Classico region 10 times, and am planning the 11th trip for this fall.
Everyone has their favorites. I’ll give you a few of mine as well, and if you want to follow up and discuss further, please contact me.
Sustainable Chianti Classico: there is a small one-man winery just north and west of Radda (not too far from Volpaia) called Caparsa. I believe its fully sustainable, and the proprietor/winemaker Paolo Cianferoni takes great pride in what he’s doing. The wines are great. When we get into Tuscany I make a beeline for their shop in Radda to stock up, or just go to the winery to visit Paolo. Incidentally, his winery is just up the road from the Osteria Panzanelle Michael mentioned.
Greve also has some cool places, and I heartily second Michael’s suggestion of Montefioralle…a great setting, lovely section of the district, and its has a great little trattoria right in the center of town, if you happen to get there for a meal. (Taverna del Guerrino)
Additionally, a little south of Greve and up a steep hilly road off the 222 is the small hamlet of Lamole. The wines are quite good, and aim for a slighty lighter version of Chianti Classicoand Chianti Classico Riserva. The gem, however, is the Ristoro di Lamole, a restaurant at the top of a hill with dramatic sunset views over some great local wines and a fine Tuscan meal.
We often spend time in and around Panzano. Its easy to get to on the 222, and has both viticultural and gastronomic delights. Le Cinciole is certainly ne of the wineries on our itinerary for this fall. Others we’ve been to (not all sustainable but all enjoyable): MonteBernardi, south of Panzano on 222 (also right up the road from Panzanelle). Run by American Michael Schmelzer, a very articulate and passionate winemaker. We also visited Villa Cafaggio west of Panzano. Lastly, although this may not be for everyone, I visited Fontodi this past trip, and was just blown away. Yes, they’re bigger and very prominent but also certified organic and have a distinctive worldview on a vertically-integrated organic agricultural system. I came away thinking “wow’ these guys have their act together. (oh, and did I mention their wines are okay, too??)
If Panzano appeals as a “stopping spot”, you might consider wandering up into the old town (up the hill toward the castle) to the Accademia del Buon Gusto. Its a small wine shop/experience run by a slightly eccentric but very knowledgable Stephano Salvadori, who specializes in local wines that don’t get much “airplay”. For lunch (or dinner) I’d also recommend the Ristorante Oltre Giardino which is right where the old section of Panzano meets the 222 junction. They have an outdoor garden/seating area that overlooks the famed “Conca D’oro” vineyards and landscape. We find a way to eat there every trip.