Montalcino is a wine town that happens to have a fortress, or maybe the other way round. It sits on a hill at about five hundred and fifty metres south of Siena, with views across the valleys of the Orcia and Ombrone rivers, and its name is known to wine lovers around the world because of Brunello, a red wine made from a local variety of Sangiovese and aged for years before release. The vineyards and olive groves cover the slopes around the town, lined with cypress, and in autumn the leaves turn the hills copper and gold.
The history is just as rich. The fortress was built in the fourteenth century by the Sienese, and it later became the last stronghold of the Republic of Siena. After Siena fell to Florentine and Spanish forces in 1555, many of its citizens retreated here and held out for four more years, a last independent flag in Tuscany. The walls are still intact and you can climb to the ramparts for the view, and the town has a lively collection of wine shops, called enoteche, where you can sample the local product. Not far away is the Abbey of Sant'Antimo, a Romanesque church in a quiet valley, which is worth visiting for its stone and its Gregorian chant.
The riding is gentle but charming. The roads around Montalcino are narrow, twisting and often lined with cypress, with the occasional white gravel strada bianca branching off. Tarmac is mostly good, but some stretches are patched, and farm traffic and cyclists are common. The climb into the town is steep, with a few tight bends, and parking in the old centre is limited. Late spring and early autumn are the best seasons, when the light is soft and the vines are green or golden. Summer is hot and the roads can be busy at weekends.
Services are fine, since the town has cafes, restaurants, bakeries and shops and has been catering to wine visitors for a long time. A glass of Rosso di Montalcino, the younger sibling of Brunello, with a plate of pici pasta or a slice of local pecorino is a very civilised pause. For fuel, though, you will need to plan. The village of Torrenieri, about six kilometres away, is the nearest stop, and larger towns such as Buonconvento and Abbadia San Salvatore have more choice.
If you ride with a pillion or sit for lunch, pace yourself. Italian police take drinking and riding seriously, and the roads here are very good at punishing the unwary.