Buonconvento sits on the Via Cassia in the valley of the Arbia river, south of Siena, a small walled town built of red brick that most travellers pass on the way to somewhere grander. That is a mistake. The walls still stand in a tidy rectangle, with a gate at each end, and inside the streets are quiet and clean, lined with old brick houses, with a long, narrow main street that gives the place an unusual, almost theatrical order. The town has a historical connection to the Holy Roman Emperor Henry VII, who died here in 1313 while on campaign in Italy.
The landscape around Buonconvento is the Crete Senesi and the Val d'Orcia, a land of bare clay hills, cypresses, wheat fields and isolated farmhouses, and the colour changes with the seasons, from the green of spring to the gold of summer and the grey of winter. The ridge-top town of Montalcino, about ten kilometres to the west, makes Brunello, one of Italy's greatest red wines, and the great abbey of Monte Oliveto Maggiore, set among cypress trees, lies a short ride to the north-east. Both are well worth the diversion.
A small museum in the town is devoted to the sharecropping system, the mezzadria, that shaped Tuscan farm life for centuries, until it was abolished in the 1960s, and it gives a good picture of how people lived and worked on these hills. The town has a number of bars and small restaurants, and a bakery or two, and it is a pleasant place for a coffee or a light lunch before the next stretch of hills. There is a Friday market on some weeks, though the days vary, so ask.
The riding around Buonconvento is some of the best in Tuscany, with long, rolling roads through the hills, open bends and fine views, though the surface can be patchy and gravel appears on the corners. Spring and autumn are the best seasons, with warm light and fewer tourists. Buonconvento has fuel in town, but stations can be thin on Sundays, so fill up in Siena or Sinalunga, about twenty-three kilometres away, which is a bigger town. In July and August the heat is serious, and shade is scarce, so carry water.