Villa de Cerreto Guidi and Historic Centre of Siena
Plan this ride
Recorded distance
298 km
Riding-time estimate
5 h 41
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.
298 km from Cerreto Guidi to Cerreto Guidi, about 5 h 41 of riding. It goes by way of Villa de Castello, Historic Centre of San Gimignano, Historic Centre of Siena and back through Historic Centre of San Gimignano. The line favours views over speed.
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. 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.
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. 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.
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. 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 102 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
Villa de Cerreto Guidi closes the day.
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 back through Historic Centre of San Gimignano
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.