Grand Duke Pietro Leopoldo of the Habsburg-Lorraine family was wont to take a tour of the Sienese Valdichiana, in order to keep an eye on the farms, see what how they were maintained and how much they were producing, as well as to enjoy the landscapes from his carriage, as it rolled along the lanes between tenancies. The same route is no less breathtaking today, as it takes in the hilltowns dotted an elevation some 300 metres above the vast Chiana marshland, which Pietro Leopoldo himself helped to drain.
We start from the municipality of Sinalunga and go past some ancient castles that once belonged to the Cacciaconti, scions of the Scialenga counts, before they passed to the Republic of Siena or other noble families. The entrance to the valley starts along the Foenna, one of the streams that was crucial in the reclamation of the marshland, near Rigomango. The name of this hilltop castle actually derives from this stream, which was considered a rigum magnum (an important watercourse), near which the original settlement was founded on the floodplain. Our route continues towards Farnetella, which according to Bartolomeo Gherardini, auditor general to an earlier Grand Duke, was in 1676 "located on a hill with good air, its walls mostly in ruins. It has two gates and three small streets". The next leg of the Leopoldian tour takes us to the medieval village of Sinalunga, originally Asinalonga (Ad Sinus Longus, which means 'in the direction of a long inlet', the inlet in question having been grooved out by the Foenna. The lower part of the town is called Pieve, and not without reason: the Peutinger Table shows the Parish Church (Pieve in Italian) of San Pietro ad Mensulas, which stands on the Via Cassia between Clusio (now Chiusi) and Sena Julia (Siena).
With Sinalunga behind you, your next stop is Trequanda. Like other places in the area - Asso, Cennano, Malcensis and Sicille, its name is Etruscan, possibly connected to the hero Tarkonte. The town venerates its daughter Bonizella Cacciaconti and the miracles that she worked. Continuing onwards, you come to the hamlets of Castelmuzio and Petroio: the former was originally called Castel Mozzo and belonged to the Sienese hospital Santa Maria della Scala, before passing to the Piccolomini family and becoming a frequent lodging for San Bernardino of Siena. Petroio, meanwhile, does not have the typical rectangular plan of Castelmuzio but also stands upon a hilltop. It is defined by its imposing tower and by the memory of Brandano, a famous preacher who was born here.
The next stop of the journey is Pienza, the wide-eyed dream of Pope Pius II, Enea Silvio Piccolomini. In just four years he had the embryo of a harmonious city, its classical fifteenth-century structures replacing the decadent Corsignano, which he renamed after himself. His death brought an end to his experiment, his quest for the ideal Renaissance city. Monticchiello follows: a castle that the Forteguerra family long ago gifted to the pope, who gave it to the Teutonic Order, before it fell into the hands of Siena. The village keeps its traditions alive, not least through its 'Poor Theatre', which brings its few inhabitants to the stage. The route continues towards Spedaletto (now in the municipality of Pienza), which operated as a granary for Santa Maria della Scala, in Siena, but which was really a fortress that happened to serve a productive function.
Next we come to Chianciano, from the Latin Clancianum, which means beyond the Chiane (swamps). Originally a stronghold, the place has become known for its hot springs. Then we arrive at Chiusi (originally Clamars, then Clusium, which signifies the dykes over the marshland). This most important of Etruscan cities declined in prestige over time, but not before making its mark with such characters as Saint Mustiola and Giovanni Graziano, considered the father of canon law. Sarteano (from the Latin Sertorios or Sarturius) and Cetona (Cis-Tuniam, meaning beyond the modern river Paglia) are two castles, with well-preserved citadels, that Orvieto and Siena fought over. San Casciano dei Bagni marks the end of the journey, which rewards the wayfarer with its sophisticated spas. These villages have all produced their share of famous people. And so you conclude a 152-km journey, either by car or by bicycle. If the latter, it is perhaps advisable to use the dirt tracks and B-roads as much as possible.
