UNESCO inscribed the Val d'Orcia in 2004 as a cultural landscape: farmland listed not for any single monument but as a deliberate work of art. The valley was reshaped between the fourteenth and fifteenth centuries, when Sienese landowners divided the chalky crete into grain estates and lined the farm drives with cypress as windbreaks. Ambrogio Lorenzetti had already painted this arrangement of fields and fortified hill towns in Siena's Palazzo Pubblico around 1338, in the fresco cycle on good government. The scenery visitors photograph today is, in effect, a medieval agricultural plan that was never overwritten. Wine followed the same slow logic. Val d'Orcia wine tasting tours converge on two appellations that Italy raised in 1980 into its first rank of DOCG wines: Brunello di Montalcino and Vino Nobile di Montepulciano. Brunello is made from Sangiovese Grosso alone and cannot be released until five years after the harvest, six for a riserva. Clemente Santi showed a Montalcino red at exhibition in the 1860s, and his descendants at Biondi-Santi are generally credited with fixing the style. Vino Nobile, aged a minimum of two years, was called the king of all wines by the physician-poet Francesco Redi in 1685. Soil does much of the arguing. Montalcino's slopes fall from roughly 120 to 650 metres, mixing galestro schist near the hilltop with heavier marine clays toward Sant'Angelo in Colle, so two bottles of the same vintage can taste a decade apart. Montepulciano works sandier Pliocene deposits, part of the reason Vino Nobile arrives softer and earlier. Orcia DOC, created in 1997 in the ground between them, remains the smallest and least exported of the three, and a degustazione there often takes place at the kitchen table of the grower. Architecture punctuates the vineyards. Pienza was rebuilt for Pope Pius II between 1459 and 1462 by Bernardo Rossellino, who compressed a cathedral, a papal palace and a town hall onto one trapezoidal square. The Romanesque abbey of Sant'Antimo stands alone in an olive valley below Montalcino, its alabaster capitals warming as the light moves. Montalcino's fortress dates from 1361; the Tempio di San Biagio, begun below Montepulciano by Antonio da Sangallo the Elder in 1518, was built in travertine the colour of bone. The valley matters now because it stayed small. Montalcino counts around 250 producers across some 2,000 hectares of Brunello vineyard, many of them family holdings of three or four hectares, while Montepulciano's cellars burrow beneath the medieval main street on Etruscan foundations. There is no gate and no entrance fee for the landscape itself; Val d'Orcia is a region rather than a venue, and each estate sets its own terms, which is why almost all of them work by appointment. A Val d'Orcia wine tasting tour is therefore a key rather than a queue, and a Tuscan wine country tour linking Pienza's pecorino cellars with the Sangiovese terraces reads as one document rather than a list of stops.