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.
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. 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.
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. 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.
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. 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.
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. 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.
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.
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.