Private tours and experiences in the Val d'Orcia

The geographic center of the valley and a historic stop on the Via Francigena pilgrim road. Inside the walls are the Romanesque collegiate church and the Horti Leonini, a sixteenth-century formal garden open to the public. Just north, on a rise beside the Cassia, stands the most photographed group of cypresses in Italy.

In 1459 Pope Pius II commissioned Bernardo Rossellino to rebuild his birthplace as an ideal Renaissance city. The result was finished in three years: a trapezoidal square, the cathedral, the papal palace and an open view toward Monte Amiata. A World Heritage Site since 1996 — eight years before the valley around it.

A tiny village where the main square is not a square but a sixteenth-century thermal basin, fifty meters long and still full of hot water. Francigena pilgrims passed through, as did Saint Catherine and Lorenzo the Magnificent. You cannot get into the pool: you look at it, which is plenty.

The Brunello hill, with its fourteenth-century fortress on top and vineyards dropping away on every side. Six miles south, at the end of an olive valley, stands the Romanesque abbey of Sant'Antimo: travertine and alabaster that go nearly translucent in the afternoon sun.

The twin hill, home of Vino Nobile, stretched along a narrow steep ridge. The town climbs to Piazza Grande; just outside the walls stands the temple of San Biagio, a centrally planned church begun in 1518 to a design by Antonio da Sangallo the Elder, alone on a lawn at the end of a cypress avenue.

The two less-trodden ends of the valley. At Monticchiello the white gravel road climbs in switchbacks between cypresses — the one in half the photographs of the valley. At Radicofani, at the other end, a medieval fortress sits on a cone of volcanic rock at 800 meters: from up there you see the whole Val d'Orcia at once.