Concierge.com's insider take:
The real Chianti is a surprisingly wild part of Tuscany, its small vineyards separated by densely wooded hills that are home to wild boar and porcupines. Wine towns such as Radda, Castellina, and Greve are prosperous and slightly anonymous; the real attraction around here lies in postcard-perfect smaller villages like Montefiorale or Volpaia, in wine-estate castles such as Brolio and Meleto, or in the area's two glorious medieval abbeys, Badia a Passignano and Badia a Coltibuono. The SS 222 Chiantigiana road winds through the area: If you have time to spare, it is a more scenic alternative to the fast Florence–Siena Superstrada. There are any number of opportunities to sample wine in the area; see Wine Touring for more details. On the second weekend of September, Greve hosts the Rassegna del Chianti Classico, the area's biggest wine fair.