Val d Orcia Scenic Road from Siena

Scenic road chapters

Waypoint introductions and full write-ups

1. 1. Siena

   Siena is the opposite of Florence in nearly every way that matters, and the Sienese would like you to remember it. It sits on three ridges in southern Tuscany, a compact medieval city of brick and stone in warm reddish-brown tones, and at its centre lies the Piazza del Campo, a vast shell-shaped square sloping down to a tall brick tower, the Torre del Mangia, about a hundred metres high. Twice each summer, on the second of July and the sixteenth of August, the square is covered with earth and ten riders from the city's districts, the contrade, race bareback around it in the Palio, a dangerous, chaotic event that lasts about ninety seconds and is felt by the whole city as a matter of honour.

   Read the complete Siena write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Siena is where the day begins. Next is Buonconvento.

2. 2. Buonconvento

   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.

   Read the complete Buonconvento write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Buonconvento comes up about 30 km into the recorded legs. Next is Montalcino.

3. 3. Montalcino

   Montalcino is a wine town that happens to have a fortress, or maybe the other way round. It sits on a hill at about five hundred and fifty metres south of Siena, with views across the valleys of the Orcia and Ombrone rivers, and its name is known to wine lovers around the world because of Brunello, a red wine made from a local variety of Sangiovese and aged for years before release. The vineyards and olive groves cover the slopes around the town, lined with cypress, and in autumn the leaves turn the hills copper and gold.

   Read the complete Montalcino write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   about 43 km into the recorded legs you reach Montalcino. Next is Pienza.

4. 4. Pienza

   Pienza is the ideal city that one man built for himself, and it is as extraordinary as that sounds. It began as a village called Corsignano, the birthplace of Enea Silvio Piccolomini, who rose to become Pope Pius II. When he returned in 1459 as pope, he decided to turn his home town into a model Renaissance city, and he hired the architect Bernardo Rossellino to do it. In only a few years, the place was rebuilt around a perfect trapezoid piazza, with a cathedral, a papal palace and a town hall, all in the new classical style. The pope died in 1464 and the plan was never completed, which is why Pienza is still so small and so perfect, like a stage set frozen in time. It was named a UNESCO World Heritage Site in 1996.

   Read the complete Pienza write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Pienza, late in the day. Next is Montepulciano.

5. 5. Montepulciano

   Montepulciano sits on a long limestone ridge at about 600 metres, overlooking the Val di Chiana to the east and the Val d'Orcia to the west, and it has the appearance of a town that has been polished by centuries of owners with taste. It is a Renaissance town, built largely by Florentine families and architects, with palaces such as the Palazzo Contucci and the Palazzo Comunale, and a main street, the Corso, that climbs in a long, steady slope toward the Piazza Grande at the top. The Duomo, the well and the town hall are here, and the view from the tower over the Tuscan hills is long.

   Read the complete Montepulciano write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Finish at Montepulciano. That is the ride.