Greve in Chianti is considered the gateway to the Chianti. This town is famous for its unique square. In medieval times, the square was the market  for the villages, castles and farms of the area. The square is  almost triangular in shape, is bordered by three sides of wide porches. You can visit the church of Santa Croce in medieval origin, but from the neo-Renaissance style which houses some precious works of sacred art, including a triptych of the Madonna and Saints by Lorenzo Bicci.
In Greve you can taste typical products of the Chianti. There museum of wine is by walking distance.  Also in the square you will find craft shops, antique shops, wine bars and restaurants.

Panzano in Chianti  Close from Greve is Panzano which has played an important role in the defense of the territories of Florence since the twelfth century.  Here you can visit the Castle of Panzano that was a fort of defense of the Republic of Florence in the wars between Florence and Siena.  The Church of St. Mary, dates back to 1200, but was completely rebuilt in 1800 in a neoclassical style. The Church of San Leolino, dating 982, that hosts precious works of art by local artists. Of course you need to try the local products.  Would you like to listen the Divine Comedy? Go to Butcher Cecchini, famous for its delicious Florentine steak, which is cut off by decanting the Divine Comedy.

Castellina in Chianti is an ancient town with Etruscan origins. Here you can visit the Etruscan tombs of Montecalvario.  You can see the fortress that dominates the central square, and the beautiful walkway of Via delle Volte that offers a breathtaking scenery. Walking through the city you can admire beautiful mansions that belonged to important families of Siena and Florence. Also worth seeing is the Church of St. Saviour thou rebuilt after the Second World War, has a beautiful fresco of a late fourteenth-century Tuscan master. Also you can visit the Archaeological Museum of the Sienese Chianti, and finally taking a rest by having a glass of wine from the region.

Radda in Chianti still retains its original medieval appearance. The ancient walls protect the city center, which is spread in a concentric maze of narrow streets. The Palazzo del Podesta and the Church of St. Nicholas of Romanesque origin are at the center of the village. On the outskirts of the town is the old Franciscan convent of Santa Maria in Prato.
The Castle of Volpaia, an ancient fortified village is near by Radda that is currently a small tourist village where you can enjoy the ancient tradition of wine.  Another fun place to visit is the Commandery of St. Eufrosino, now home to a wine cellar. 

Gaiole in Chianti is close to Radda, and its  origins date back to the Middle Ages. This colorful town is a major tourist attraction, and in the old times it was an important market place for the surrounding castles. Places to visit the Castle of Vertine and Castle Orchard. As any other place of the Chianti region, a must is of course to sit down, and enjoy a glass of wine with local products.