Via Chiantigiana and Crete Senesi Loop 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 Asciano.

2. 2. Asciano

   South of Siena the Tuscan hills lose their vines and cypress and turn into something stranger: the Crete Senesi, a landscape of bare, rounded clay hills the colour of a wet pigeon, cut by gullies that geologists call calanchi. Asciano is the town that sits at the heart of it. It is a compact brick-and-stone place inside medieval walls, with a handful of churches, a small collection of Etruscan and sacred art in its museums, and a main street that the locals walk up and down in the evening. Nobody comes to Asciano for a famous monument, and that is the nice thing about it.

   Read the complete Asciano write-up.

   Recorded stop-planning note

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

   Planning note

   Asciano comes up about 41 km into the recorded legs. Next is Abbazia Monte Oliveto Maggiore.

3. 3. Abbazia Monte Oliveto Maggiore

   At the end of a long avenue of cypress trees, in a hollow of the clay hills south of Siena, stands a great red-brick monastery. Monte Oliveto Maggiore was founded in the early fourteenth century by a Sienese nobleman who gave up his career and his comforts to live as a hermit, and who was soon joined by others. They built here, on what was then a wild and wooded slope, and the community grew into the mother house of the Olivetan Benedictines. The abbey is still home to a small number of monks, and it feels like it: quiet, ordered and slightly outside time.

   Read the complete Abbazia Monte Oliveto Maggiore write-up.

   Recorded stop-planning note

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

   Planning note

   about 50 km into the recorded legs you reach Abbazia Monte Oliveto Maggiore. Next is Buonconvento.

4. 4. 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, late in the day. Next is Siena.

5. 5. Siena

   Return visit. Read the place description above.

   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

   Back at Siena. That is the ride.