Montalcino sits on a hilltop above a sea of vineyards and olive groves, and it has been making a wine that carries its name around the world. Brunello di Montalcino is made from a local clone of the Sangiovese grape, aged for years in oak and in bottle, and in 1980 it was among the first wines in Italy to be awarded the highest quality classification, DOCG. A glass of it with a plate of cured meats or a thick stew of wild boar, called cinghiale, is the classic way to eat here, and the menu in most trattorie follows that rhythm.
The town is small and handsome, with narrow stone streets climbing to a fourteenth-century fortress, built by Siena, that dominates the skyline. The history of the fortress holds a strange footnote. When Siena fell to Florence and its Spanish allies in 1555, a group of Sienese loyalists withdrew to Montalcino and kept the idea of the republic alive for four more years, until 1559. A short walk takes you up to the walls, and the view across the vines and the distant Monte Amiata is worth it. In the countryside to the south, the Romanesque abbey of Sant'Antimo stands in a quiet valley of olive trees, and if you arrive when the monks are singing, the sound in the stone church is memorable.
For a rider, Montalcino is a lunch and a pause, a place to park, walk and eat slowly. The ride in from the Val d'Orcia or from Buonconvento is a series of gentle curves through vineyards, with good surfaces and open views, and the road up to the town is short and steep. Parking near the centre is limited, so use the lots at the edge and walk in. Streets are narrow and cobbled, and boots with a bit of grip help.
Food is the reward. Besides cinghiale, look for pici, thick hand-rolled pasta served with garlic and tomato or with a rich meat sauce, and for pecorino cheese from the nearby Pienza area, often paired with honey. Many restaurants close in the afternoon, so aim for lunch before two, and book ahead on weekends and in the harvest season. If you plan to taste wine, remember that you are riding, and a sip is enough.
Fuel is at Torrenieri and Buonconvento, and the larger town of Abbadia San Salvatore is farther away, so fill up before you climb. In the evening, the walls glow and the town quietens, which is the best hour to be there.