You're in Montalcino, one of the best wine regions in the world. These are the names worth knowing.

Restaurants:

• Il Leccio, Sant'Angelo in Colle. 5 min from the borgo, great for a long lunch.
• Boccon Divino, just outside Montalcino's walls. Terrace looking down the Val d'Orcia; order the Chianina.
• Il Giglio, inside the walls. Picture windows over the valley; the pheasant liver pâté with Moscatello is a thing.
• Osteria di Porta al Cassero, by the fortress. Rustic family place, pici with aglione and cinghiale stew.
• Re di Macchia, in the centre. Small room, handmade pici with wild boar ragù, deep Brunello list.

Wineries (all by appointment):

• Castiglion del Bosco, on the estate. Ask about the Campo del Drago cru.
• Biondi-Santi, just outside town. The family that invented Brunello — reverential, strict, and the reference point.
• Il Poggione, Sant'Angelo in Colle. Benchmark traditionalist with a deep library.
• Col d'Orcia, Sant'Angelo in Colle. Large organic estate, welcoming tasting program.
• Altesino, north of town. Pioneered the single-vineyard idea; go for the Montosoli.
• Caparzo, north of town. Polished modern style, easy to visit.
• Poggio Antico, south of town. High ridge, cool-site Brunello, sweeping views.
• Mastrojanni, Castelnuovo dell'Abate. Illy-family owned; the Schiena d'Asino cru is the one.
• Argiano, south-west. Historic hilltop villa with some of the best-rated releases of recent years.
• Eredi Fuligni, east side. Small classicist family estate, old-school and refined.

Other things worth doing:

• The Abbey of Sant'Antimo, a 12th-century Romanesque abbey in an olive grove, 15 min from the borgo.
• The Fortezza, Montalcino's 14th-century fortress. Walk the ramparts, then taste Brunello at Enoteca La Fortezza inside the walls.
• Madonna del Soccorso, the belvedere behind the sanctuary. Best free view in town, five minutes from the walls — go at sunset.
• Bagno Vignoni, a medieval village built around a thermal pool, about 20 min away.
• E-bike loop through the Brunello vineyards down to Sant'Antimo and back.
• Truffle hunting with a local guide and their dogs, usually ending in lunch.