Concierge.com's insider take:
Montalcino is famous for Brunello, probably Italy's most famous red wine—and also one of the most expensive. Combine history and enology with a visit to the formidable Rocca, a 14th-century fortress with a wine bar offering tastes of various local vintages (Piazzale Fortezza; 39-0577-849-211; www.enotecalafortezza.it). Five miles south on a lovely country road, the Abbey of Sant'Antimo (39-0577-835-659; www.antimo.it), a Romanesque masterpiece with an interior partially decorated in translucent alabaster, has beautiful light. It also enjoys magnificent acoustics, as you will hear if you catch the traditional Gregorian chant sung seven times daily by the community of French monks that recently recolonized this formerly abandoned monastery. Between Montalcino and Sant'Antimo, the collection of rural artifacts, photos, and documents at the Museo della Comunità di Montalcino e del Brunello on the Fattoria dei Barbi estate is well worth a look.