The city of Castellina in Chianti is located atop a hill at the crossroads of important roads that cross the Arbia, Elsa and Pesa valleys. Set along the Chiantigiana road that connects Florence to Siena, it is one of the most important destinations in Chianti.
It is a small city and there while there isn't that many things to see and do, we recommend a stop here to enjoy a nice walk along the main street, always crowded and with a long history. If you decide to include it in your Chianti tour, you have to drive to Castellina. As a matter of fact it's not well connected to other destinations in Chianti. The best connections are to and from Siena, but there is only one bus early in the morning to Greve in Chianti and Florence and this is really a shame.
The city's origins go back to Etruscan times and came under Florentine control starting in the 12th century when it became an important outpost due to its strategic position between Florence and Siena. It was destroyed and rebuilt many times during the battles between the two cities and every time the town was reconstructed with bigger defensive walls. Legend has it that even Brunelleschi was asked to work on the project of new walls for the town.
Along the ancient walls an impressive underground tunnel used by the guards back then remains, now called Via della Volte which today is a fascinating tunnel with shops and restaurants. I suggest you walk down the tunnel during different times of the day so that you can admire the view of the surrounding Chianti countryside with various degrees of light from the small windows along the tunnel. The tunnel itself goes around the city and encloses the delightful city center, itself divided by its main street, Via Ferruccio. Here you'll find many shops, workshops, restaurants and important palaces such as Palazzo Banciardi and Palazzo Squarcialupi, both belonging to local noble families. Inside Palazzo Squarcialupi the Enoteca Antiquaria is now housed, a wine shop for over a 100 years old which represents an important historical archive of wine and which has helped preserving the original characteristics of Chianti Classico wine itself.
The Church of San Salvatore deserves a visit. It was rebuilt in 1945 after the devastation of WWII but which still displays a valuable fresco by Lorenzo Bicci depicting the Virgin Mary with Child and a wooden statue from the Renaissance. A few steps away from the city center, the Fortress with its tall tower offers a stunning panorama of the town and countryside. Inside the Fortress is the headquarters of the Municipality and the Archeological Museum of Chianti, displaying important archeological findings from the surroundings that testify the ancient origins of the Chianti region.
Within walking distance from the historical center I recommend stopping at the Antica Delizia, a wonderful ice cream shop where you should enjoy a giant delicious gelato. I also recommend a visit to the Etruscan tomb of Montecalvario in the surroundings, an important remnant of Etruscan necropolis architecture.