Built in 1361, Montalcino’s dramatic 5-sided fortress encloses a cobbled courtyard and chapel, and is topped by crenelated ramparts and soaring towers. Explore the fortress on a wine tour from Florence, Rome, or Siena: take in the views over the vineyards and olive groves of the Val d’Orcia and sit down for a tasting of local Brunello wines in the cellar wine shop. Most wine-tasting day trips stop in a number of picturesque villages that dot Tuscany’s wine country—including Montepulciano, Pienza, and San Gimignano—and include lunch featuring Tuscany’s famed cuisine.
By car, take the SR2 highway south from Siena and walk up to the fortress from the historic center. Arriving by public transportation involves multiple bus connections, so visiting with a tour that includes transportation is a more convenient option.
One of the biggest draws of the Fortezza di Montalcino is the views over the surrounding countryside, particularly beautiful in spring and fall. Otherwise, choose a clear, mild day so you can enjoy visiting the outdoor ramparts and towers.
In the Middle Ages, Montalcino was an important town thanks to its proximity to the Via Francigena pilgrimage route between France and Rome, but after falling under the control of the Republic of Siena, the town was often embroiled in skirmishes over territory with Florence. Montalcino was the last Tuscan town to hold out against the might of the Medicis: Siena fell in 1555 and Montalcino was subjected to a four-year siege, though the fortress never fell to Florentine troops. Cosimo I added its imposing ramparts in 1571, but the Fortezza 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.