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.
From Casalecchio di Reno it runs 310 km to Casalecchio di Reno; allow about 5 h 50 of riding. The stops in between: Vena del Gesso Romagnola - M.te Penzola, Villa de Cafaggiolo, Historic Centre of Florence and back through Villa de Cafaggiolo. 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 28 km this is Chiantigiana Wine Road, a road with a name of its own and a reason for it.
Chapter facts
Length
28 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, 43 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 Historic Centre of Florence.
4. Historic Centre of Florence
Florence is the kind of city where the problem is not finding something to look at but deciding when to stop. The historic centre sits on a bend of the Arno, a compact grid of Roman origin with the Duomo at its middle, Brunelleschi's dome rising over the roofs, the Palazzo Vecchio at the civic heart and the Ponte Vecchio, the only bridge the retreating Germans spared in 1944. The Medici bankers who ran the place for much of the fifteenth to eighteenth centuries paid for most of what you are about to see, and they were rather good at it.
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
San Luca closes the day.
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 Historic Centre of Florence
Villa de Cafaggiolo → Historic Centre of Florence is 28 km of rhythm rather than effort. Let it flow and let the view breathe.
Historic Centre of Florence to back through Villa de Cafaggiolo
Historic Centre of Florence → back through Villa de Cafaggiolo is 28 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.