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 wine.

• 45km, 1170m climb

• 3h 49m moving, 6h 49m elapsed

• 38% off-road, Sunny, 18°C average, 34°C max

Brutalist Architecture in Sorgane

The route starts in Florence, the capital of Renaissance art and culture. But as you leave the city, the route takes a detour to Sorgane, a suburb south of the Arno river that features some striking examples of brutalist architecture. These buildings, constructed in the 1960s and 1970s, use concrete as a structural and aesthetic element, creating geometric shapes and patterns that contrast with the surrounding landscape. Some of them look like they are made of notched wooden planks that are joined together in creative ways. If you are a fan of modern architecture, you will find this area fascinating.

A Secret View over Florence

After admiring the brutalist buildings, you immediately start climbing up the forested hills that overlook Florence. This is where the off-road fun begins, as you will encounter some dirt paths that will test your skills and patience. But don't worry, the effort will be worth it when you reach a hidden spot that offers a breathtaking view over the city. You can see the iconic Duomo, the Ponte Vecchio, and the Palazzo Vecchio from a different perspective, surrounded by greenery and tranquility. This is a perfect place to take a break and snap some photos.

Roadie's Dreams in Chianti

After enjoying the view, you descend off-road and join some bigger roads, and lesser gravel tracks until you reach Strada in Chianti, a small town that marks the entrance to the famous wine region. From here, you will follow the Via Chiantigiana, a road that is popular among road cyclists for its smooth asphalt and gentle hills. You will pass through vineyards, olive groves, and cypress trees, as well as charming villages like Greve in Chianti and Panzano in Chianti. These towns are worth a stop for their picturesque piazzas, cafes, restaurants, and shops. You can also visit the museum of Gino Bartali, a legendary Italian cyclist who won the Tour de France twice and helped save Jews during World War II.

Gravel Fun in Panzano

After Panzano, you will leave the asphalt behind and enter another gravel section that will take you up towards another hill town called Volpaia. This road is steep but not too bad, and it offers some great views of the countryside. You will also pass by some big villas and farms that produce some of the best Chianti wines.

The downhill gamble

The next part of the route is more of a gamble, as it is not on any official maps or guides. But if you follow Strava heat maps or your intuition, you will find a rough double track that leads you down towards Radda in Chianti. This is not for the faint-hearted, as you will have to navigate big rocks and ruts that will challenge your balance and brakes. But if you like adrenaline and adventure, this is the most fun part of the trip. You will feel like you are exploring uncharted territory.

The uphill not so fun bit

After that downhill fun, the next part is tough. Very steep and I had to get off my bike and push. Not a good look.

A Relaxing Night in Radda

After surviving the downhill section, you will arrive at Radda in Chianti, your final destination for the day. This is a charming and historic wine town that dates back to the 9th century. You can stroll around its narrow streets and admire its medieval buildings and walls. You can also visit the Casa del Chianti Classico, a former convent that houses a museum and a wine bar where you can learn more about the history and production of Chianti wine.

For your accommodation, I recommend Camere e Appartamenti Baldini Romanita, a wonderful B&B that offers cozy rooms, friendly service, and amazing breakfasts. The owner also provides one of the best Chianti I have ever tasted as a welcome. You can enjoy a glass or a bottle on her terrace overlooking the hills.

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.