Montalcino is a hilltown and comune in Tuscany, Italy. It is famous for its Brunello di Montalcino wine.

The town is located to the west of Pienza, close to the Crete Senesi in Valdorcia. It is 42 km from Siena, 110 km from Florence and 150 km from Pisa.

The first medieval walls were built in the 13th century. The fortress was built at the highest point of the town in 1361, on a pentagonal plan designed by the Sienese architects, Mino Foresi and Domenico di Feo. The fortress incorporates some of the pre-existing southern walls, the pre-existing structures including the keep of Santo Martini, the San Giovanni tower and an ancient basilica which now serves as the castle chapel.

Down the narrow, short street that extends from the main gate of the fortress is the Chiesa di Sant'Agostino with its simple Romanesque façade, also built in the 13th century.

The building adjacent to the church is a one-time convent, but it is now the home of the Musei Riuniti which is both a civic and diocesan museum. The museums hold various works, including a gorgeous wooden crucifix by an unknown artist of the Sienese school, two beautiful 15th century wooden sculptures and several other sculptures in terracotta which appear to be of the Della Robbia school. The collection also includes a St Peter and St Paul by Ambrogio Lorenzetti and a Virgin and Child by Simone Martini.

The Duomo (cathedral), dedicated to San Salvatore, was originally built in the 14th Century, but it now has a neo-classical appearance thanks to extensive renovation work that was done in the early 19th century under the direction of Sienese architect Agostino Fantasici.

The main piazza, the Piazza del Popolo, is downhill from the fortress and Duomo on the via Matteotti. The principle building on the piazza is the town hall, once the Palazzo dei Priori (built late 13th, early 14th century) but now the Palazzo Comunale. The palace is adorned with the coats of arms of the Podesta who once ruled the city. A very high medieval tower is incorporated into the palazzo. Close by is a Renaissance structure with six round arches, called La Loggia, which was started at the very end of the 14th century and finished in the early 15th, but which has undergone much restoration work over the subsequent centuries.

Montalcino is divided, like most medieval Tuscan cities, into quarters called contrade. The thirteenth-century church of San Francesco in the Castlevecchio contrada has undergone several renovations. Some of the interior frescoes were done by Vincenzo Tamagni in the early sixteenth century.

There are many other medieval buildings in Montalcino that make up its centro storico (historical center). As with many other similar cities, money from tourism is aiding the cause of restoration and preservation.