Iteranti
A pale gravel road winding along a Tuscan hillside above rolling vineyards and olive groves stretching to a hazy horizon.

Florence to Radda

Ridden · Jamie Brammer

Florence isn’t on the Via Francigena but I wanted to know what the gravel routes were like between there and Siena. So as a warm up for finishing the Via Francigena I did two days of gravel cycling through Chianti towards Siena. I created my own route trying to plot a reasonably direct and “sightseeing friendly” yet off-road route between Florence and Siena. So if you are looking for a challenging and scenic cycle route that takes you through the heart of Tuscany, you might want to try this off-road adventure from Florence to Radda. This route covers about 45 km with a good propotion of gravel and dirt roads. There’s some steep climbs and descents, but rewards you with stunning views, historic towns, and delicious food.

Route map

Open in Google Maps

Highlights

  • Brutalist architecture on the way out of Florence in Sorgane. Where the buildings seem to use concrete to join different bits of them together as a child might do when playing with notched wooden planks.
  • A wonderful, almost secret, view over Florence from the forested hills just above Sorgane.
  • Some of the roads between Strada i Chianti and Greve i Chianti. Roadie’s dreams. Gentle hills. Smooth asphalt.
  • Greve i Chianti, very pretty small town in the heart of the wine growing region.
  • The road out of Greve i Chianti up to the hill town of Panzano. Gravel. Steep, but not too bad. Big villas. Good fun.
  • Panzano has great views and a couple of great restaurants; I think I ate in one of them. Oh and the church was cool too.
  • The road out of Panzano up the next hill… yes you keep going up after Panzano. Perhaps the best gravel road of the entire trip, though would perhaps have been more fun coming down it.
  • The route down the hill after that. This was more of a gamble as it’s not on any real route maps. But Stava heat maps showed a few people going that way. This isn’t gravel; perhaps best described as very rough double track. You’d not be cycling up this but it was great fun navigating the big rocks and ruts.
  • Special mention to where I stayed the night. A wonderful B&B in Radda (Camere e Appartamenti Baldini Romanita): the best Chianti I’ve ever drunk and a breakfast so tasty and so large that I felt very guilty have to leave some of it.

Lowlights

  • A bit unfair, but the final climb to Radda was a monster! I couldn’t do all of it on my bike… yes the usual gearing excuse.
  • A loaded orange bikepacking bike leaning against an ornate lamppost base on a cobbled city street, with a church tower visible among the buildings beyond.
  • A suburban street lined with balconied apartment blocks and parked cars, with a signpost reading "Quartiere n.3" pointing along the road.
  • A tiered concrete apartment block with stepped terraces and external stairways overlooking a courtyard where cars are parked.
    Sorgane, brutalist architecture
  • Wild cyclamen flowers with swept-back pink petals growing from a mossy bank amid fallen autumn leaves.
  • A loaded orange bikepacking bike leaning against a wooden fence post on a grassy hillside track, with a hazy town visible in the valley below.
    "Secret" view of Florence
  • Florence's domed cathedral and bell tower rising above the hazy city, framed between trees on a hillside overlook.
  • A misty Tuscan valley at dawn with a white villa and cypress trees emerging above low fog, hills silhouetted beyond.
  • A gravel track lined with tall cypress trees and a wooden fence, with a signpost reading "Case al Prato" and "Il Borgo di Vignamaggio".
  • A stone church with a bell tower and clock, its steps lined with pink flowers and a sign reading "Pace a voi", a loaded orange bike parked at the foot of the stairs.
    Ponzano
  • Empty wooden pews inside a stone church lead down the nave to an altar beneath a painted apse depicting a crowd gathered around a risen figure.
  • A pale gravel road winding along a Tuscan hillside above rolling vineyards and olive groves stretching to a hazy horizon.
  • A gravel road descending through dappled shade beneath overhanging trees, with a triangular hillside gradient warning sign at the roadside.
  • A wide gravel track curving past scrubby bushes, with a sweeping view over layered wooded hills under a partly cloudy sky.
    Serious gravel after Ponzano
  • A rough, eroded stony track cutting through woodland, its surface rutted with loose pale rocks and gullies.
  • A loaded orange bikepacking bike propped against a low stone wall beside a calm, tree-lined stream.
  • A cluster of Italian road signs warning of a 15% gradient, a slippery bend, a rough surface, snow chains, a 30 km/h limit and a lorry ban marked "eccetto autorizzati", with a loaded orange bike parked beneath them.
  • A large black rooster statue, the Chianti Classico emblem, mounted on a red plinth on a paved terrace overlooking distant hills.
    Radda
  • A rounded stone corner tower of an old building rising above a narrow paved lane, seen from below against a sky streaked with vapour trails.
  • Diners seated under parasols outside Caffè San Niccolò at dusk, beside an ornate stone lion-head fountain set into an arched wall.
  • The interior of a rustic Italian trattoria with laid tables and wine glasses beneath shelves crammed with wine bottles, and a barman behind the counter.