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CURVESCOUT / MOTORCYCLE RIDE

Villa de Cerreto Guidi and Val d'Orcia

Plan this ride

Recorded distance
376 km
Riding-time estimate
7 h 36
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

376 km from Cerreto Guidi to Cerreto Guidi, about 7 h 36 of riding. It goes by way of Villa de Castello, 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 48 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.

Chapter facts
Length
48 km
Named road
Chiantigiana Wine Road

Waypoint introductions and full write-ups

  1. 1. 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 is where the day begins. Next is Villa de Castello.

  2. 2. Villa de Castello

    The Villa di Castello stands on the north-western edge of Florence, in the flat land below Monte Morello, and the huge city has grown right up to its gates. Sesto Fiorentino, a town of forty-five thousand people, is three kilometres away, and the centre of Florence a few more. The villa is one of the Medici villas that UNESCO inscribed in 2013, and it is an unusual one, because the garden is the main attraction and the house inside is plain.

    Read the complete Villa de Castello write-up.

    Recorded stop-planning note

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

    Planning note

    Villa de Castello comes up about 42 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 102 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 179 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 228 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 272 km into the recorded legs you reach back through Historic Centre of San Gimignano. Next is back through Villa de Castello.

  8. 8. back through Villa de Castello

    Return visit. Read the place description above.

    Read the complete Villa de Castello 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 Castello, late in the day. Next is Villa de Cerreto Guidi.

  9. 9. 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

    The route ends here after 376 km.

Leg by leg

Villa de Cerreto Guidi to Villa de Castello

Villa de Cerreto Guidi → Villa de Castello is 42 km of rhythm rather than effort. Let it flow and let the view breathe.

Villa de Castello to Historic Centre of San Gimignano

Villa de Castello → Historic Centre of San Gimignano is 60 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 de Castello

back through Historic Centre of San Gimignano → back through Villa de Castello is 63 km of rhythm rather than effort. Let it flow and let the view breathe.

back through Villa de Castello to Villa de Cerreto Guidi

back through Villa de Castello → Villa de Cerreto Guidi is 42 km of rhythm rather than effort. Let it flow and let the view breathe.

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