The classic Chianti route is the S222 from Florence to Castellina: either zip straight down to Siena or explore more deeply by heading east on the S429 through Radda and Gaiole before turning south on the S408 for Siena. But that only takes in the highlights. To truly get a feel for Chianti, explore the back roads to Passignano, Coltibuono and other towns off the beaten path. Bus services (infrequent!) also connect the main towns.
TRAVEL GUIDE- PLACES TO VISIT IN CHIANTI By Tripnmate, you can easily select a holiday rental in Chianti and try our recommended list to visit nearby places.
1. Montefioralle This 14th-century hamlet, hovering directly above Greve, consists of a single circular street, two churches and fantastic views over the valley and on to the 10th-century Pieve di San Cresci church below the walls.
2. Pieve di San Leolino Just south of Panzano lies this little Romanesque church with several Sienese paintings from the 13th to 15th centuries and a pretty little brick cloister.
3. Castellina in Chianti The most medieval of the Chianti League towns, with a glowering Rocca fortress. Via della Volte – a tunnel-like road pierced by “windows” overlooking the countryside – was a soldiers’ walk when this was Florence’s last outpost before Siena.
4. Ipogeo di Montecalvario A perfect 6th-century BC tomb, with four passages tunnelling into the burial chambers. There is a light switch beside the gate.
5. Badia a Coltibuono This abbey from 770 includes an 11th-century church, Lorenza de’ Medici’s cookery school and a classy restaurant run by her son Paolo.
6. Panzano in Chianti This often-overlooked town (view from town above) is the home of Dario Cecchini (arguably Italy’s best butcher) and a couple of fine enoteche, where you can sample local wines with snacks
7. Radda in Chianti The only hilltop member of the Chianti league (great views) is capped by the 15th-century Palazzo del Podestà studded with stone coats of arms of past mayors. There’s another good butcher/grocer’s here called Luciano Prociatti.