Val d'Orcia and Crete Senesi are the most recognisable face of the Tuscan countryside: hills shaped by farming, rows of cypresses, medieval villages perched on the ridges and clay "biancane" that change colour with the light. Six stages trace a loop of about 120 kilometres across two UNESCO landscapes, three world-famous wines and a handful of free thermal springs open all year round.
San Quirico is the natural gateway to Val d'Orcia: a medieval village enclosed by its walls, with the Romanesque Collegiata and the Horti Leonini, a sixteenth-century Italian garden open to the public. It is the ideal starting point because it brings together, within a short radius, the three elements you will find throughout the itinerary: a Romanesque parish church, a noble palace and farmland. Just outside the walls, the road to Pienza offers the view of the Madonna di Vitaleta chapel, one of the most photographed images in Tuscany.
A few minutes from San Quirico, Bagno Vignoni is unique in Italy: in place of the central square there is a large sixteenth-century pool fed by thermal springs that gush out at 52°C. The village can be visited on foot in half an hour and is surrounded by free thermal springs and historic spas. The walk along the Parco dei Mulini, carved into the travertine rock, reveals the ancient hydraulic systems that have harnessed the thermal water since the Middle Ages.
Pienza is the "ideal city" commissioned by Pope Pius II Piccolomini in the fifteenth century: the original village, Corsignano, was redesigned in just a few years by the architect Bernardo Rossellino according to Renaissance principles. The result is one of the most harmonious squares in Italy, overlooking the papal palace, the cathedral and the view of Val d'Orcia. Pienza is also the capital of Pecorino di Pienza DOP: in the shops of the centre you can taste ageings from fresh to reserve, including versions matured in walnut leaves and hay.
Montalcino dominates the Orcia valley from the top of its fourteenth-century fortress. It is the home of Brunello, one of the most recognised Italian reds in the world: the Fortezza houses the Enoteca La Fortezza, which brings together the labels of the area's leading producers. Outside the centre, the Abbey of Sant'Antimo is one of the finest Romanesque churches in Italy, set among olive trees and vineyards: the ten-kilometre detour is worth it for the silence of the cloister alone.
Montepulciano is reached by crossing the hills of Vino Nobile, the other great red of the Siena area. The village develops along an uphill "corso" that culminates in Piazza Grande, dramatic and overlooking the Town Hall, the Cathedral and the Well of the Griffins and Lions. The historic cellars are dug into the basements of the town's noble palaces: visiting one means descending thirty metres below street level and walking among large barrels of Slavonian oak.
From Montepulciano you head north along secondary roads to enter the Crete Senesi: a landscape different from Val d'Orcia, harsher, made of clay hills, "biancane" and badlands. Asciano is the main town of the area: the civic archaeological museum holds first-rate Etruscan finds and the parish church of Sant'Agata is a fine Romanesque church in travertine. From Asciano start the most famous white gravel roads in the province, ridden every year by L'Eroica and Strade Bianche, a world-class cycling race.
The best times are late spring, when the wheat is still green and the hills turn red with poppies, and early autumn, with the grape harvest and the warm colours on the vineyards. Mid-summer is beautiful but hot and crowded, especially in Pienza and Montepulciano. Winter offers unusual views, particularly when the fog settles over the Crete. The car remains the most practical means, but many sections lend themselves to cycling (gentle white roads) and some villages are linked by short trails: from Bagno Vignoni you can walk down to the Orcia river in twenty minutes.
Val d'Orcia is one of the Italian areas with the highest concentration of farm stays: restored stone farmhouses, country houses with a pool overlooking the cypresses, organic farms with country cooking. Staying in an agriturismo here means waking up to the sound of livestock, having breakfast with unsalted Tuscan bread and fresh pecorino, and reaching each stage in less than half an hour. The properties around San Quirico, Pienza and Montalcino often offer tastings of their own wines and traditional dinners on request: a way to experience the area beyond the visit to the villages.
