The dominant feature of Montalcino's skyline is the 14th-century Sienese Fortezza (Fortress), expanded in 1571 by Duke Cosimo I. Inside the old keep is the Enoteca La Fortezza wine shop (tel. 0577-849-211; www.enotecalafortezza.com), where you can buy tickets to circumnavigate 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 10am to 6pm.
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 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). On the palazzo's exterior wall are attached rows of outsized acrylic wine labels. The town commissions one each year from a leading international designer to mark the vintage -- the number of stars (up to five) on each denotes the "quality" of the year's harvest. 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 slender 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. Just to the right of the church, in its former convent, is the Musei di Montalcino (tel. 0577-846-014; www.museisenesi.org). The museum is dedicated largely to Sienese works, including a panel by Ambrogio Lorenzetti and four extraordinary carved Crucifixions from the 1300s. It's one of the best small-town collections in Tuscany, and has been supplemented by a new archaeological section displayed in an atmospheric cellar. The museum is open Tuesday through Sunday from 10am to 1pm and 2 to 5:30pm. Admission is 4.50€ adults and 3€ for children 11 and under; a 6€ cumulative ticket also gets you into the Fortezza.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.