A rural drive that is an Italian classic is the Strada Chiantigiana, or the SR 222. The back road goes through Tuscany’s wine country through to the small cities and towns of Chianti including Greve, Radda, and Giaole, situated between Florence and Siena. The road runs south adjacent to a network of two lane secondary roads, and has beautiful vistas of Tuscan vineyards and rolling hills before reaching the connection to Sienna.
This 100 km drive has some of the most beautiful scenery in all of Europe. Allow plenty of time to visit local wineries and restaurants, and walk in the winding streets of the diverse towns and meet the locals.
About 35 km outside of Florence is Greve, which is home to the region’s biggest tourism information center, so you will definitely want to stop there. Grab some brochures, and sit at one of the coffee shops or wine bars of the Piazza Matteotti, before buying some supplies for your picnic or other favorite recreational activities. If you are there in September, attend the annual wine fair from Greve, which is a major event for Chianti.
You are sure to find the symbol of a black rooster when you find yourself in the center of Gallo Nero country and also sample some Chianti Classico wine. You might want to see some beautiful medieval castles located in the district.
If you travel south for another 10 km, you will find the medieval town of Panzano, which was erected around the remnants of a castle, beside the Strada Chiantigiana. At Enoteca il Vinaio you can partake of light meals and local wines while you admire the vast vineyards from the terrace. Panzano’s San Leolino church, built in the Romanesque style and only 1 km south of town, is located on a picturesque hill and houses several Renaissance frescoes.
Only twelve kilometers southward from Panzano lies the hill top town of Castellina, a major crossroads during the Etruscan era, and a region which was battled over by neighboring Florence and Siena. Panzano has several Etruscan remains, including four tombs and a well, as well as many palaces from the medieval period, which are still standing.
From here, you could detour twenty kilometers toward the east, traveling via Volpaia to the vicinity of Radda and Gaiole. There are more Etruscan ruins and wine estates located 6 km north of Volpaia. Retrace your steps and take the turn to Gaiole, to visit the Badia a Coltibuono, which is an abbey nestled near a forest of cedar trees. Wee rustic churches and aged castles surround Gaiole’s market town. The restored Castello del Brolio is open for visits, and located south of the city. You can see Siena and the hills beyond from here.
Returning to the Strada Chiantigiana, drive the remaining thirty kilometers south to Siena. The centre of the city is very pedestrian-friendly, and contains a medieval palazzi and many shops, cafes, and places to eat along its narrow pathways. The world famous Piazza del Campo is covered with straw and dirt two times per year for the exciting Palio di Siena, the heart stopping bareback horse race.