The dominant feature of Montalcino's skyline is the 14th-century Sienese fortress, expanded in 1571 by Duke Cosimo I. The inside is now a pretty little park; duck through the archway into a small garden planted with ilex trees on a plateau with a view of the valley. Inside the old keep is the Enoteca La Fortezza wine shop (tel. 0577-849-211; www.enotecalafortezza.it), where you can buy tickets to climb up onto the ramparts for panoramic views of the Val d'Orcia and Vallombrone. In one of the castle rooms, the last battle standard of the Sienese Republic is preserved. April through October, the fortress is open daily from 9am to 8pm; November through March, hours are Tuesday through Sunday from 9am to 6pm. Admission is 3.50€ ($4.55) adults and 1.50€ ($1.95) children under 12. A 6€ ($7.80) cumulative ticket also gets you into the Museo Civico e Diocesano, but you must buy it at the museum .
Walk down Via dell'Oca and turn left on Via Panfilo to Piazza Garibaldi, with the small 11th-century church of Sant'Egidio. Inside is a frescoed triptych by Francesco Cozza and a Madonna and Saints by Luca di Tommé.
Out the other end of the piazza, Costa del Municipio leads past the entrance to the Palazzo Comunale (1292), which houses a small display on the history of Brunello and other Montalcino wines and the headquarters of the wine consortium. The elongated front of the palazzo on Piazza del Popolo, sporting the mayoral coat of arms of past podestà, looks far too narrow to stand. It's nothing more than a slender clock tower with a loggia off the left side. On the long piazza you'll find a 14th- to 15th-century loggia and the 19th-century cafe Fiaschetteria Italiana, focal point of the evening passeggiata up Via Mazzini.
A stepped street leads uphill from Piazza del Popolo to the 14th-century church of Sant'Agostino, rarely open these days, but which has lots of frescoes covering the walls, including the Life of St. Augustine by Bartolo di Fredi in the choir.
Just to the right of the church, in its former convent, is the Museo Civico e Diocesano (tel. 0577-846-014) a good little grouping of 12th- to 16th-century Sienese paintings and sculpture. The most important works are some 12th-century illuminated Bibles; Madonna and Child paintings by Luca di Tommé, Simone Martini, Vecchietta, and Sano di Pietro; and several good Bartolo di Fredi works. There are also 15th-century glazed terra cottas by Andrea della Robbia and a passel of 14th- and 15th-century polychrome wood statues in excellent repair, including some by Francesco di Valdambrino and Domenico Cafaggi. The museum is open Tuesday through Sunday: January through March from 10am to 1pm and 2 to 5:40pm and April through December from 10am to 5:50pm (might close 1-2pm if staffing is short). Admission is 4.50€ ($5.85) adults and 3€ ($3.90) under 12; or you can buy a 6€ ($7.80) cumulative ticket that also gets you into the fortress .
