Gessi Bolognesi and Historic Centre of San Gimignano
Plan this ride
Recorded distance
442 km
Riding-time estimate
8 h 23
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.
A 442 km round trip from Rastignano-Carteria di Sesto - roughly 8 h 23 in the saddle. On the way it passes Vena del Gesso Romagnola - M.te Casino, Villa de Cafaggiolo, Villa de Poggio a Caiano and 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 41 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.
Chapter facts
Length
41 km
Named road
Chiantigiana Wine Road
Waypoint introductions and full write-ups
1. Gessi Bolognesi
Ride south out of Bologna and within ten minutes the city's suburbs give way to something surprising: a range of low hills made of gypsum, a soft, crystalline rock that dissolves in water and forms caves, sinkholes and strange, shiny outcrops. These are the Gessi Bolognesi, a protected regional park between the Savena and Idice valleys, and in 2023 they became part of the UNESCO site for the evaporitic karst and caves of the northern Apennines.
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Gessi Bolognesi is where the day begins. Next is Vena del Gesso Romagnola - M.te Casino, 45 km on.
2. Vena del Gesso Romagnola - M.te Casino
Crystals the size of a hand catch the sun along the Vena del Gesso, a ridge of selenite gypsum that runs for some twenty-five kilometres across the hills of Romagna, from the Sillaro valley to the Lamone. The rock formed millions of years ago when the Mediterranean dried up and its salts were deposited, and it has since been carved by water into caves, sinkholes and blind valleys. In 2023, UNESCO listed the evaporite karst and caves of the northern Apennines, and the Vena del Gesso is the heart of it. Monte Casino is one of the peaks on the ridge, near Borgo Tossignano and Casola Valsenio.
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Vena del Gesso Romagnola - M.te Casino comes up about 57 km into the recorded legs. Next is Villa de Cafaggiolo.
3. Villa de Cafaggiolo
In the green bowl of the Mugello, north of Florence, the Medici family kept a house long before they ruled the city. Cafaggiolo was an old family property, and around the middle of the fifteenth century Cosimo the Elder had the architect Michelozzo transform it into a fortified country villa, with battlements, a tower and a moat, a cross between a castle and a farmhouse. Lorenzo the Magnificent spent time here as a boy, and the villa became a favourite retreat for hunting and escaping the plague in the city. It is one of the Medici Villas and Gardens in Tuscany listed by UNESCO, and visits depend on current restoration and opening arrangements, so check before you arrive.
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
about 122 km into the recorded legs you reach Villa de Cafaggiolo. Next is Villa de Poggio a Caiano.
4. Villa de Poggio a Caiano
Of all the Medici villas, Poggio a Caiano is the one that changed architecture. Lorenzo the Magnificent commissioned it from Giuliano da Sangallo in the 1480s, and the result was something new: a country house raised on an arcaded platform, with a portico topped by a classical pediment, the first time a temple front had been put on a private villa since antiquity. Palladio would develop the idea in the Veneto decades later. Inside, the great hall is decorated with frescoes by Andrea del Sarto, Pontormo and others, and Pontormo's lunette of Vertumnus and Pomona, with its lazy figures lounging on a wall, is one of the most charming paintings of the Renaissance. The villa is part of the UNESCO listing of the Medici Villas and Gardens in Tuscany.
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Villa de Poggio a Caiano, about halfway. Next is Historic Centre of San Gimignano.
5. 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
The route ends here after 442 km.
Leg by leg
Gessi Bolognesi to Vena del Gesso Romagnola - M.te Casino
Gessi Bolognesi → Vena del Gesso Romagnola - M.te Casino is 57 km of rhythm rather than effort. Let it flow and let the view breathe.
Vena del Gesso Romagnola - M.te Casino to Villa de Cafaggiolo
Vena del Gesso Romagnola - M.te Casino → Villa de Cafaggiolo is 65 km of rhythm rather than effort. Let it flow and let the view breathe.
Villa de Cafaggiolo to Villa de Poggio a Caiano
Villa de Cafaggiolo → Villa de Poggio a Caiano is 41 km of rhythm rather than effort. Let it flow and let the view breathe.
Villa de Poggio a Caiano to Historic Centre of San Gimignano
Villa de Poggio a Caiano → Historic Centre of San Gimignano is 57 km of rhythm rather than effort. Let it flow and let the view breathe.
Historic Centre of San Gimignano to back through Villa de Poggio a Caiano
Historic Centre of San Gimignano → back through Villa de Poggio a Caiano is 56 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Villa de Poggio a Caiano to back through Villa de Cafaggiolo
back through Villa de Poggio a Caiano → back through Villa de Cafaggiolo is 42 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Villa de Cafaggiolo to back through Vena del Gesso Romagnola - M.te Casino
back through Villa de Cafaggiolo → back through Vena del Gesso Romagnola - M.te Casino is 65 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Vena del Gesso Romagnola - M.te Casino to Gessi Bolognesi
back through Vena del Gesso Romagnola - M.te Casino → Gessi Bolognesi is 58 km of rhythm rather than effort. Let it flow and let the view breathe.