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.
A 306 km round trip from Siena - roughly 5 h 31 in the saddle. The stops in between: Historic Centre of San Gimignano, Villa de Cerreto Guidi, Piazza del Duomo and back through Villa de Cerreto Guidi. 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 44 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.
Chapter facts
Length
44 km
Named road
Chiantigiana Wine Road
Waypoint introductions and full write-ups
1. 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 is where the day begins. Next is Historic Centre of San Gimignano.
2. 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
Historic Centre of San Gimignano comes up about 44 km into the recorded legs. Next is Villa de Cerreto Guidi.
3. 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
about 94 km into the recorded legs you reach Villa de Cerreto Guidi. Next is Piazza del Duomo.
4. Piazza del Duomo
Nothing prepares you for that first glimpse through the gateway. A wide green lawn, and set on it like ornaments on a cloth, the white marble cathedral, the round baptistery, the cemetery cloister of the Camposanto, and of course the bell tower, leaning at an angle that looks wrong no matter how many photographs you have seen. The Piazza del Duomo in Pisa, also called the Field of Miracles, was one of the first places in Italy to be listed by UNESCO, back in 1987.
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Historic Centre of Siena closes the day.
Leg by leg
Historic Centre of Siena to Historic Centre of San Gimignano
Historic Centre of Siena → Historic Centre of San Gimignano is 44 km of rhythm rather than effort. Let it flow and let the view breathe.
Historic Centre of San Gimignano to Villa de Cerreto Guidi
Historic Centre of San Gimignano → Villa de Cerreto Guidi is 50 km of rhythm rather than effort. Let it flow and let the view breathe.
Villa de Cerreto Guidi to Piazza del Duomo
Villa de Cerreto Guidi → Piazza del Duomo is 58 km of rhythm rather than effort. Let it flow and let the view breathe.
Piazza del Duomo to back through Villa de Cerreto Guidi
Piazza del Duomo → back through Villa de Cerreto Guidi is 59 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Villa de Cerreto Guidi to back through Historic Centre of San Gimignano
back through Villa de Cerreto Guidi → back through Historic Centre of San Gimignano is 50 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Historic Centre of San Gimignano to Historic Centre of Siena
back through 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.