Why this ride
A 170 km round trip from San Gimignano - roughly 3 h 46 in the saddle. The stops in between: Historic Centre of Siena, Val d'Orcia and back through Historic Centre of Siena. The line favours views over speed.
CURVESCOUT / MOTORCYCLE RIDE
Historic Centre of San Gimignano and Val d'Orcia
Plan this ride
- Recorded distance
- 170 km
- Riding-time estimate
- 3 h 46
- Journey
- Recorded itinerary
Distance and timing basis
Ordered leg totals agree within rounding. Stop distances are approximate sums of rounded legs. Stops, delays, approach and any separate return travel add time. Basis: producer-declared routed record.
Reading history stays on this device. My road watch requires a separate selection; opening it does not subscribe this ride.
Distance and riding time are measured on the routed road. Check local closures and conditions before you ride.
Scenic road chapters
Chiantigiana Wine Road
Expect company on a summer weekend. Early is better than fast. For about 47 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.
Chapter facts
- Length
- 47 km
- Named road
- Chiantigiana Wine Road
Waypoint introductions and full write-ups
1. Historic Centre of San Gimignano
Seen from the surrounding countryside, San Gimignano looks like a medieval Manhattan: a cluster of stone towers rising from a hilltop above vineyards and olive groves in the Val d'Elsa. In its heyday, in the thirteenth and fourteenth centuries, the town had dozens of them, built by rival families as symbols of power and wealth. Fourteen survive, enough to make it one of the most recognisable towns in Italy and a UNESCO World Heritage site since 1990.
Read the complete Historic Centre of San Gimignano write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Historic Centre of San Gimignano is where the day begins. Next is Historic Centre of Siena.
2. Historic Centre of Siena
Siena sits on three ridges in the heart of Tuscany, a red-brick medieval city that has hardly changed its shape in seven hundred years. At its centre is the Piazza del Campo, a sloping, shell-shaped square paved in brick and divided into nine sections, a reminder of the Council of Nine that governed the city in its golden age. The Palazzo Pubblico, with the slender Torre del Mangia, stands at the bottom of the square, and inside are frescoes by Ambrogio Lorenzetti showing the effects of good and bad government, painted in the fourteenth century.
Read the complete Historic Centre of Siena write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Historic Centre of Siena comes up about 47 km into the recorded legs. Next is Val d'Orcia.
3. Val d'Orcia
Every photograph you have ever seen of Tuscany with a farmhouse on a bare hill, a winding line of cypresses and a soft haze over rolling fields was probably taken somewhere close to here. The Val d'Orcia is the valley of the river Orcia, south of Siena, a farmed landscape that Renaissance landowners deliberately shaped to look like the paintings of their time. UNESCO listed it in 2004 as a landscape designed with an idea in mind, and on a clear morning that idea is very easy to grasp.
Read the complete Val d'Orcia write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
about 85 km into the recorded legs you reach Val d'Orcia. Next is back through Historic Centre of Siena.
4. back through Historic Centre of Siena
Return visit. Read the place description above.
Read the complete Historic Centre of Siena write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
back through Historic Centre of Siena, late in the day. Next is Historic Centre of San Gimignano.
5. Historic Centre of San Gimignano
Return visit. Read the place description above.
Read the complete Historic Centre of San Gimignano write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Back at Historic Centre of San Gimignano. That is the ride.
Leg by leg
Historic Centre of San Gimignano to Historic Centre of Siena
Historic Centre of San Gimignano → Historic Centre of Siena is 47 km of rhythm rather than effort. Let it flow and let the view breathe.
Historic Centre of Siena to Val d'Orcia
Historic Centre of Siena → Val d'Orcia is 38 km of rhythm rather than effort. Let it flow and let the view breathe.
Val d'Orcia to back through Historic Centre of Siena
Val d'Orcia → back through Historic Centre of Siena is 40 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Historic Centre of Siena to Historic Centre of San Gimignano
back through Historic Centre of Siena → Historic Centre of San Gimignano is 45 km of rhythm rather than effort. Let it flow and let the view breathe.