Why this ride
439 km from Bologna to Bologna, about 8 h 08 of riding. It goes by way of Vena del Gesso Romagnola - M.te Penzola, Villa de Cafaggiolo, Villa de Poggio a Caiano and Historic Centre of San Gimignano. The line favours views over speed.
CURVESCOUT / MOTORCYCLE RIDE
Pavaglione and Historic Centre of San Gimignano
Plan this ride
- Recorded distance
- 439 km
- Riding-time estimate
- 8 h 08
- 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.
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. Pavaglione
Not many places have a portico named after a silk market, but Bologna is not many places. The Pavaglione is the long, wide arcade that runs along the side of the Palazzo dell'Archiginnasio, near the great Piazza Maggiore, and its name comes from the pavilion, a tent or covered market where silk cocoons were once traded. Bologna was a major centre of silk production in the late Middle Ages and Renaissance, and the water-powered mills of the city, fed by canals from the Reno, supplied thread to much of Europe. A stroll under the arches today, among the shops and cafés, is a stroll through that history.
Read the complete Pavaglione write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Pavaglione is where the day begins. Next is Vena del Gesso Romagnola - M.te Penzola, 46 km on.
2. Vena del Gesso Romagnola - M.te Penzola
The Santerno valley climbs south from Imola into the Apennines toward Tuscany, and about fifteen kilometres up, the river cuts through a ridge of shining grey-white rock. This is the western end of the Vena del Gesso Romagnola, the gypsum vein that runs across this part of Romagna, and Monte Penzola rises above the village of Borgo Tossignano, with Fontanelice and Casalfiumanese nearby.
Read the complete Vena del Gesso Romagnola - M.te Penzola write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Vena del Gesso Romagnola - M.te Penzola comes up about 58 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.
Read the complete Villa de Cafaggiolo write-up.
Recorded stop-planning note
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.
Read the complete Villa de Poggio a Caiano write-up.
Recorded stop-planning note
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.
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 sits at 183 km, about halfway. Next is back through Villa de Poggio a Caiano.
6. back through Villa de Poggio a Caiano
Return visit. Read the place description above.
Read the complete Villa de Poggio a Caiano write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
back through Villa de Poggio a Caiano comes up about 276 km into the recorded legs. Next is back through Villa de Cafaggiolo.
7. back through Villa de Cafaggiolo
Return visit. Read the place description above.
Read the complete Villa de Cafaggiolo write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
about 318 km into the recorded legs you reach back through Villa de Cafaggiolo. Next is back through Vena del Gesso Romagnola - M.te Penzola, 45 km on.
8. back through Vena del Gesso Romagnola - M.te Penzola
Return visit. Read the place description above.
Read the complete Vena del Gesso Romagnola - M.te Penzola write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
back through Vena del Gesso Romagnola - M.te Penzola, late in the day. Next is Pavaglione.
9. Pavaglione
Return visit. Read the place description above.
Read the complete Pavaglione write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
The route ends here after 439 km.
Leg by leg
Pavaglione to Vena del Gesso Romagnola - M.te Penzola
Pavaglione → Vena del Gesso Romagnola - M.te Penzola is 58 km of rhythm rather than effort. Let it flow and let the view breathe.
Vena del Gesso Romagnola - M.te Penzola to Villa de Cafaggiolo
Vena del Gesso Romagnola - M.te Penzola → Villa de Cafaggiolo is 64 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 Penzola
back through Villa de Cafaggiolo → back through Vena del Gesso Romagnola - M.te Penzola is 63 km of rhythm rather than effort. Let it flow and let the view breathe.
back through Vena del Gesso Romagnola - M.te Penzola to Pavaglione
back through Vena del Gesso Romagnola - M.te Penzola → Pavaglione is 58 km of rhythm rather than effort. Let it flow and let the view breathe.