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CURVESCOUT / MOTORCYCLE RIDE

Villa de Il Trebbio and Val d'Orcia

Plan this ride

Recorded distance
380 km
Riding-time estimate
7 h 50
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.

Open this ride in CurveScout

Why this ride

From Barberino di Mugello it runs 380 km to Barberino di Mugello; allow about 7 h 50 of riding. It goes by way of Villa de Artimino, 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.

Scenic road chapters

Chiantigiana Wine Road

Expect company on a summer weekend. Early is better than fast. For about 51 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.

Chapter facts
Length
51 km
Named road
Chiantigiana Wine Road

Waypoint introductions and full write-ups

  1. 1. Villa de Il Trebbio

    The Medici came from the Mugello, and Il Trebbio is one of the places where you can see it. The family's rise to Florentine power in the fifteenth century began in these hills north of the city, among farms and woods where they held land long before they held banks and palaces. Il Trebbio is a fortified villa near San Piero a Sieve, redesigned for Cosimo the Elder by the architect Michelozzo, and its crenellated walls, tower and gardens mark it as a country retreat that is also, quietly, a statement of status. It is one of the Medici villas listed by UNESCO in 2013.

    Read the complete Villa de Il Trebbio write-up.

    Recorded stop-planning note

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

    Planning note

    Villa de Il Trebbio is where the day begins. Next is Villa de Artimino.

  2. 2. Villa de Artimino

    The Medici liked to hunt, and Ferdinando I wanted somewhere to do it. In the late sixteenth century the grand duke commissioned the architect Bernardo Buontalenti to build him a hunting lodge on the hill of Artimino, west of Florence, and the result was a large, plain and strangely beautiful villa with a loggia, a terrace and a forest of chimneys. It is nicknamed the villa of the hundred chimneys, though there are fewer than that, and the stacks along the roofline give the building a rhythm that you can recognise from a long way off. It is one of the Medici villas and gardens that UNESCO listed in 2013 for the way they shaped the Italian idea of a country house.

    Read the complete Villa de Artimino write-up.

    Recorded stop-planning note

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

    Planning note

    Villa de Artimino comes up about 51 km into the recorded legs. Next is Historic Centre of San Gimignano.

  3. 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 109 km into the recorded legs you reach Historic Centre of San Gimignano. Next is Historic Centre of Siena.

  4. 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. 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 168 km, about halfway. Next is back through Historic Centre of Siena.

  6. 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 232 km into the recorded legs. Next is back through Historic Centre of San Gimignano.

  7. 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 276 km into the recorded legs you reach back through Historic Centre of San Gimignano. Next is back through Villa de Artimino.

  8. 8. back through Villa de Artimino

    Return visit. Read the place description above.

    Read the complete Villa de Artimino 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 Artimino, late in the day. Next is Villa de Il Trebbio.

  9. 9. Villa de Il Trebbio

    Return visit. Read the place description above.

    Read the complete Villa de Il Trebbio 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 380 km.

Leg by leg

Villa de Il Trebbio to Villa de Artimino

Villa de Il Trebbio → Villa de Artimino is 51 km of rhythm rather than effort. Let it flow and let the view breathe.

Villa de Artimino to Historic Centre of San Gimignano

Villa de Artimino → Historic Centre of San Gimignano is 58 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 Artimino

back through Historic Centre of San Gimignano → back through Villa de Artimino is 53 km of rhythm rather than effort. Let it flow and let the view breathe.

back through Villa de Artimino to Villa de Il Trebbio

back through Villa de Artimino → Villa de Il Trebbio is 51 km of rhythm rather than effort. Let it flow and let the view breathe.

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