Why this ride
352 km from Florence to Florence, about 7 h 04 of riding. It goes by way of Villa de Cerreto Guidi, Historic Centre of San Gimignano, Historic Centre of Siena and Val d'Orcia. The line favours views over speed.
CURVESCOUT / MOTORCYCLE RIDE
Villa de Careggi and Val d'Orcia
Plan this ride
- Recorded distance
- 352 km
- Riding-time estimate
- 7 h 04
- 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 45 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.
Chapter facts
- Length
- 45 km
- Named road
- Chiantigiana Wine Road
Waypoint introductions and full write-ups
1. Villa de Careggi
Cosimo de' Medici chose a quiet slope just north of Florence for his country house, and in the late 1450s he had the architect Michelozzo rebuild an older castle-like farmhouse at Careggi into a villa. It was not a grand showpiece. It was a working retreat where a banker who ran a city without holding office could think, farm, and entertain scholars. Cosimo died here in 1464, and so did his grandson Lorenzo the Magnificent in 1492, which makes the walls rather weighty with Florentine history.
Read the complete Villa de Careggi write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Villa de Careggi is where the day begins. Next is Villa de Cerreto Guidi.
2. Villa de Cerreto Guidi
Cosimo I de' Medici liked to hunt, and in the 1560s he had a villa built on a hilltop at Cerreto Guidi, on the edge of the marshes and woods west of Florence, where the game was plentiful. From the outside it is austere, a solid block of stone facing a square, but the approach is spectacular: a pair of great brick ramps, known as the Medici bridges, zigzag up to the entrance. The villa is part of the UNESCO listing of the Medici Villas and Gardens in Tuscany, and it holds a dark legend. Cosimo's daughter Isabella died here in 1576, and the story goes that she was murdered by her husband, Paolo Giordano Orsini, for her alleged infidelity. Whether it is true or not, it is told to every visitor.
Read the complete Villa de Cerreto Guidi write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Villa de Cerreto Guidi comes up about 43 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 93 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 172 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 216 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 260 km into the recorded legs you reach back through Historic Centre of San Gimignano. Next is back through Villa de Cerreto Guidi.
8. back through Villa de Cerreto Guidi
Return visit. Read the place description above.
Read the complete Villa de Cerreto Guidi 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 Cerreto Guidi, late in the day. Next is Villa de Careggi.
9. Villa de Careggi
Return visit. Read the place description above.
Read the complete Villa de Careggi 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 352 km.
Leg by leg
Villa de Careggi to Villa de Cerreto Guidi
Villa de Careggi → Villa de Cerreto Guidi is 43 km of rhythm rather than effort. Let it flow and let the view breathe.
Villa de Cerreto Guidi to Historic Centre of San Gimignano
Villa de Cerreto Guidi → Historic Centre of San Gimignano is 50 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 Cerreto Guidi
back through Historic Centre of San Gimignano → back through Villa de Cerreto Guidi is 50 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Villa de Cerreto Guidi to Villa de Careggi
back through Villa de Cerreto Guidi → Villa de Careggi is 42 km of rhythm rather than effort. Let it flow and let the view breathe.