The lovely Tuscan hilltop town of Montalcino is world-famous for its rich red Brunello wines, but it also has a spectacular centro storico, with winding streets that lead up to the imposing five-sided Montalcino Fortress (Fortezza di Montalcino). Built in 1361 on top of earlier medieval structures, the site today includes a cobbled courtyard enclosed by sturdy watchtowers and a medieval chapel as well as a top-quality enoteca (wine shop) for tasting and selling the local Brunellos. The ramparts are open to walk around, offering spectacular views of the vineyards and olive groves of the Val d’Orcia.

In the Middle Ages, Montalcino was a settlement of considerable importance thanks to its proximity to the Via Francigena pilgrimage route between France and Rome, but under control of the Republic of Siena it became consistently embroiled in territory warfare with Florence. It was the last Tuscan town to hold out against the might of the Medicis, and although Siena fell in 1555 and despite a four-year siege, Montalcino's fortress never fell to Florentine troops. Cosimo I added its imposing ramparts in 1571, but the fortress lost its military significance soon after; over the years it housed a community of Benedictine monks but gradually fell into disrepair before restorations took place in the 1940s.