Historic Centre of Siena and Villa de Cerreto Guidi

Scenic road chapters

Waypoint introductions and full write-ups

1. 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.

   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 is where the day begins. Next is Historic Centre of San Gimignano.

2. 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.

   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

   Historic Centre of San Gimignano comes up about 44 km into the recorded legs. Next is Villa de Cerreto Guidi.

3. 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.

   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

   about 94 km into the recorded legs you reach Villa de Cerreto Guidi. Next is back through Historic Centre of San Gimignano.

4. 4. 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

   back through Historic Centre of San Gimignano, late in the day. Next is Historic Centre of Siena.

5. 5. 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 at Historic Centre of Siena. That is the ride.