Why this ride
414 km from Fiesole to Fiesole, about 7 h 54 of riding. On the way it passes Villa La Magia, Historic Centre of San Gimignano, Historic Centre of Siena and Val d'Orcia. It was put together for the scenery rather than the shortest line.
CURVESCOUT / MOTORCYCLE RIDE
Villa Medici de Fiesole and Val d'Orcia
Plan this ride
- Recorded distance
- 414 km
- Riding-time estimate
- 7 h 54
- 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 40 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.
Chapter facts
- Length
- 40 km
- Named road
- Chiantigiana Wine Road
Waypoint introductions and full write-ups
1. Villa Medici de Fiesole
Fiesole sits on a hill above Florence, and it has looked down on the city for much longer than Florence has existed. The Etruscans founded a settlement here, and the Romans built a theatre, baths and a temple that are still visible. When the Medici came to power in the fifteenth century they chose the slope below Fiesole for a country villa, and Giovanni de' Medici, the younger son of Cosimo, commissioned Michelozzo to design one around 1450. The result, Villa Medici, is built on terraces cut into the hillside, with a loggia that opens out over a sweeping view of the Arno valley and the dome of Florence cathedral.
Read the complete Villa Medici de Fiesole write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Villa Medici de Fiesole is where the day begins. Next is Villa La Magia.
2. Villa La Magia
The Medici loved the countryside, especially when it came with hunting grounds, and Villa La Magia at Quarrata was one of their country retreats at the foot of the Montalbano hills, a few kilometres south of Pistoia. Francesco I de' Medici bought it in the sixteenth century to use as a hunting lodge, and it belongs to the World Heritage inscription for the Medici villas and gardens of Tuscany. The villa is a solid rectangular building around a courtyard, more farmhouse than palace, with a park that has become home to contemporary art installations, a rather unexpected touch for a Renaissance hunting lodge.
Read the complete Villa La Magia write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Villa La Magia comes up about 40 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 121 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 177 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 247 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 291 km into the recorded legs you reach back through Historic Centre of San Gimignano. Next is back through Villa La Magia.
8. back through Villa La Magia
Return visit. Read the place description above.
Read the complete Villa La Magia write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
back through Villa La Magia, late in the day. Next is Villa Medici de Fiesole.
9. Villa Medici de Fiesole
Return visit. Read the place description above.
Read the complete Villa Medici de Fiesole 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 414 km.
Leg by leg
Villa Medici de Fiesole to Villa La Magia
Villa Medici de Fiesole → Villa La Magia is 40 km of rhythm rather than effort. Let it flow and let the view breathe.
Villa La Magia to Historic Centre of San Gimignano
Villa La Magia → Historic Centre of San Gimignano is 81 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 48 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 La Magia
back through Historic Centre of San Gimignano → back through Villa La Magia is 86 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Villa La Magia to Villa Medici de Fiesole
back through Villa La Magia → Villa Medici de Fiesole is 37 km of rhythm rather than effort. Let it flow and let the view breathe.