The pleasure of roaming the Chianti is discovering a great winery or crenellated castle all on your own, but you might be interested in some tips: the following towns are all considered Chianti D.O.C. You will encounter them on a meandering circuit that heads northwest out of Siena on the Chiantigiana (SS222). Many of these villages merit a stop and almost everywhere you will find a good place to sample the wine or have a bite to go with it.
Castellina in Chianti
Leaning on a hillside that is a watershed of the three rivers that greatly influenced the history of this area, the Arbia, the Pesa and the Elsa, Castellina has Etruscan origins and an aristocratic medieval history, still seen in the patrician homes and ancient Rocca fortress commissioned by Lorenzo de Medici to protect the city. Via delle Volte, a tunnel running beneath Renaissance dwellings, affords breathtaking views of the Chianti out of tiny openings in the tunnel walls, which originally served the purpose of defence rather than tourism.
Via delle Volte - an atmospheric spot for a restaurant. Ristorante Sotto le Volte
Radda in Chianti
Radda in Chianti Radda is a village of vineyards and the unofficial capital of the Chianti. Its wealth is seen in its many 15th & 16th century palaces which rise amid the medieval buildings. From the Piazza Ferrucci, in which are located the Palazzo Pretorio and Romanesque church of San Niccolò, to the circuit of its fortified walls and the cultivated landscape beyond, it is obvious that Radda knew its livelihood was wed to agriculture.
This area appreciates its artists, be they the ancient ones whose gold smithing and stained glass can be admired in the Romanesque church of Santa Maria Novella, dating back to the year 1000, or the fanciful modern sculptures peeking out of the woods in the Parco Sculture del Chianti in nearby Pievasciata.
Gaiole in Chianti
Mercato Unlike the other important Chianti centres founded for defence, Gaiole in Chianti has always been a centre of commerce. Markets have been here for centuries, from the early ones that served the nearby castles, to modern local ones that are still held every week like clockwork. Currently Gaiole is famous for its production of cold meats from the Cinta Senese pig, but there are numerous other precious foodstuffs to tempt the visitor.