Sitting on a high ridge, Castellina is believed to be built on the ruins of a Roman settlement. Despite multiple attacks, Castellina’s Rocca castle is still standing tall and is the evidence this town was once the strategic headquarters between Florence and Siena. Climb the tower of the castle and get marvelous views over the countryside.

Today, the castle is home to the Archeological Museum of Chianti, exhibiting all kinds of archeological finds from the region from the Bronze Age up to the Middle Ages. Next to the castle, you find Via delle Volte, a remarkable arched passage with small artistic shops and nice places to eat.

Castellina in Chianti is a perfect place to stay for the night; here you can unwind, overlooking the hills, enjoying a glass of wine of one of the local wineries and indulge a nice dinner.