Why this ride
366 km from Scarperia to Scarperia, about 7 h 30 of riding. On the way it passes Villa de Poggio a Caiano, Historic Centre of San Gimignano, Historic Centre of Siena and Val d'Orcia. The line favours views over speed.
CURVESCOUT / MOTORCYCLE RIDE
Villa de Cafaggiolo and Val d'Orcia
Plan this ride
- Recorded distance
- 366 km
- Riding-time estimate
- 7 h 30
- 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 41 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.
Chapter facts
- Length
- 41 km
- Named road
- Chiantigiana Wine Road
Waypoint introductions and full write-ups
1. Villa de Cafaggiolo
In the green bowl of the Mugello, north of Florence, the Medici family kept a house long before they ruled the city. Cafaggiolo was an old family property, and around the middle of the fifteenth century Cosimo the Elder had the architect Michelozzo transform it into a fortified country villa, with battlements, a tower and a moat, a cross between a castle and a farmhouse. Lorenzo the Magnificent spent time here as a boy, and the villa became a favourite retreat for hunting and escaping the plague in the city. It is one of the Medici Villas and Gardens in Tuscany listed by UNESCO, and visits depend on current restoration and opening arrangements, so check before you arrive.
Read the complete Villa de Cafaggiolo write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Villa de Cafaggiolo is where the day begins. Next is Villa de Poggio a Caiano.
2. Villa de Poggio a Caiano
Of all the Medici villas, Poggio a Caiano is the one that changed architecture. Lorenzo the Magnificent commissioned it from Giuliano da Sangallo in the 1480s, and the result was something new: a country house raised on an arcaded platform, with a portico topped by a classical pediment, the first time a temple front had been put on a private villa since antiquity. Palladio would develop the idea in the Veneto decades later. Inside, the great hall is decorated with frescoes by Andrea del Sarto, Pontormo and others, and Pontormo's lunette of Vertumnus and Pomona, with its lazy figures lounging on a wall, is one of the most charming paintings of the Renaissance. The villa is part of the UNESCO listing of the Medici Villas and Gardens in Tuscany.
Read the complete Villa de Poggio a Caiano write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Villa de Poggio a Caiano comes up about 41 km into the recorded legs. Next is Historic Centre of San Gimignano.
3. 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
about 100 km into the recorded legs you reach Historic Centre of San Gimignano. Next is Historic Centre of Siena.
4. 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, about halfway. Next is Val d'Orcia.
5. 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
Val d'Orcia sits at 170 km, about halfway. Next is back through Historic Centre of Siena.
6. 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 comes up about 223 km into the recorded legs. Next is back through Historic Centre of San Gimignano.
7. back through 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
about 267 km into the recorded legs you reach back through Historic Centre of San Gimignano. Next is back through Villa de Poggio a Caiano.
8. back through Villa de Poggio a Caiano
Return visit. Read the place description above.
Read the complete Villa de Poggio a Caiano write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
back through Villa de Poggio a Caiano, late in the day. Next is Villa de Cafaggiolo.
9. Villa de Cafaggiolo
Return visit. Read the place description above.
Read the complete Villa de Cafaggiolo write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
The route ends here after 366 km.
Leg by leg
Villa de Cafaggiolo to Villa de Poggio a Caiano
Villa de Cafaggiolo → Villa de Poggio a Caiano is 41 km of rhythm rather than effort. Let it flow and let the view breathe.
Villa de Poggio a Caiano to Historic Centre of San Gimignano
Villa de Poggio a Caiano → Historic Centre of San Gimignano is 59 km of rhythm rather than effort. Let it flow and let the view breathe.
Historic Centre of San Gimignano to Historic Centre of Siena
Historic Centre of San Gimignano → Historic Centre of Siena is 45 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 back through Historic Centre of San Gimignano
back through Historic Centre of Siena → back through Historic Centre of San Gimignano is 44 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Historic Centre of San Gimignano to back through Villa de Poggio a Caiano
back through Historic Centre of San Gimignano → back through Villa de Poggio a Caiano is 58 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Villa de Poggio a Caiano to Villa de Cafaggiolo
back through Villa de Poggio a Caiano → Villa de Cafaggiolo is 41 km of rhythm rather than effort. Let it flow and let the view breathe.