Villa du Poggio Imperiale and Historic Centre of San Gimignano
Plan this ride
Recorded distance
298 km
Riding-time estimate
5 h 39
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.
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Distance and riding time are measured on the routed road. Check local closures and conditions before you ride.
298 km from Florence to Florence, about 5 h 39 of riding. It goes by way of Villa de Il Trebbio, Villa de Cerreto Guidi, Historic Centre of San Gimignano 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 30 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.
Chapter facts
Length
30 km
Named road
Chiantigiana Wine Road
Waypoint introductions and full write-ups
1. Villa du Poggio Imperiale
Poggio Imperiale announces itself with an avenue, a long, straight, cypress-lined approach running up from Porta Romana in Florence, with statues in niches and the villa waiting at the top like the end of a sentence. It began as a Medici property in the sixteenth century, but its grand form came in the 1620s, when Maria Maddalena of Austria, wife of Cosimo II, enlarged it and gave it the name Imperiale in a nod to her Habsburg origins. The cool neoclassical front you see today was added in the early nineteenth century under Napoleonic rule.
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Villa du Poggio Imperiale is where the day begins. Next is Villa de Il Trebbio.
2. 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 comes up about 30 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 101 km into the recorded legs you reach Villa de Cerreto Guidi. Next is Historic Centre of San Gimignano.
4. 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.