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 449 km round trip from Casalecchio di Reno - roughly 8 h 18 in the saddle. 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. 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 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. San Luca
The Sanctuary of the Madonna di San Luca sits on the Colle della Guardia, a green hill above Bologna, and what makes it special is the way you reach it. A covered arcade, nearly four kilometres long and with some six hundred and sixty arches, climbs from the edge of the city to the church, built between 1674 and 1793 so pilgrims could carry an icon of the Virgin down into town and back in the rain. It is the longest portico in the world, and it forms part of the arcades of Bologna that UNESCO listed in 2021. The icon, which tradition says was painted by Luke the Evangelist, is taken in procession to the cathedral each May.
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
San Luca 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.
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 64 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 128 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
about 323 km into the recorded legs you reach back through Villa de Cafaggiolo. Next is back through Vena del Gesso Romagnola - M.te Penzola, 46 km on.
8. back through Vena del Gesso Romagnola - M.te Penzola
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
The route ends here after 449 km.
Leg by leg
San Luca to Vena del Gesso Romagnola - M.te Penzola
San Luca → Vena del Gesso Romagnola - M.te Penzola is 64 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 41 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 San Luca
back through Vena del Gesso Romagnola - M.te Penzola → San Luca is 62 km of rhythm rather than effort. Let it flow and let the view breathe.