One of Chianti’s most charming hilltop villages, Castellina was fortified by Florence as an outpost against Siena, and for centuries its fortunes depended on who was on top in their endless war. It was lost to a combined Sienese-Aragonese siege in 1478, although after the fall of Siena itself in 1555 Florence lost interest in Castellina, and today it looks much as it did in the quattrocento: the circuit of walls is almost intact, complete with houses built into and on top of them.
The Rocca, or fortress, is in central Piazza del Comune; its mighty donjon and covered walkway, the Via delle Volte, were part of the 15th-century defensive works. Since 2006 it has been home to the Museo Archeologico del Chianti Senese with finds from around the region, including Greek black figure vases and a reconstructed, ornate Etruscan chariot found nearby at the Ipogeo Etrusco di Montecalvario, a recently restored 7th-century BC Etruscan tumulus a 10 min walk north of the center on Via Fiorentina.
There are many splendid old farmhouses and villas around Castellina, nearly all former fortifications along Chianti’s medieval Maginot Line, the border between Siena and Florence. These include the Villa La Leccia just southwest of Castellina, and the Castello di Campalli near Fonterutoli, an ancient hamlet south on the Chiantigiana (typically, both of these are now hotels). In the 13th century Florence and Siena often met here to work out peace settlements, none of which endured very long. More vestiges of Etruscan tombs can be seen near Fonterutoli at the Necropoli del Poggino (along with a lovely view over Siena).
Hours: Apr, May, Sept & Oct, daily 10-6pm; June-Aug, daily 11-7pm; Nov-Mar, Sat & Sun 10-5pm; Adm: €5.
+39 0577 742090
Images by: Vignaccia76, tassilo111