The village of Castelgiocondo overlooks the historic estate of the Frescobaldis in Montalcino: an ancient stronghold built in 1100 to defend the road leading from the sea to Siena. The property is one of the first 4 to begin producing Brunello di Montalcino in 1800, and its historic importance is represented on the label of Castelgiocondo by the figure of a condottiere from a celebrated fresco of the Sienese artist Simone Martini.