Published on: 2 February 2014 | Last updated: 3 January 2020
This route takes you through through the heart of Toscana: the Chianti, the Crete Senesi, and the Val d’Orcia. Great cycling between some of Italy’s great art cities. It links the UNESCO world-heritage listed cities of Firenze, Siena, San Gimignano, and Pienza, as well as the Val d’Orcia. It also takes you to Volterra another of the great Tuscan cities. There are lots of other places to see and visit in Toscana, these would probably figure on most people’s must-see list.
The route takes you to Radicofani on the border with the Lazio region, and almost to the gates of Rome, but a great alternative would be to see the other side of Toscana by linking this tour with either the Gran Tour della Maremma the Grand Tour della Val di Merse. Two excellent signposted routes through the south and west of the region, blissfully quiet roads and even more beautiful Tuscan hilltop towns and scenery.
There’s an option to take the direct route going from Firenze to Siena and then to Pienza. However, to my mind it would be a real shame to miss out on San Gimignano and Volterra - not just because the cities themselves are well worth seeing but also because there’s some lovely riding between them.
This tour is more suitable for experienced cyclists: I opted for the scenic roads, but inevitably during the summer they draw other tourists, so some of the roads used are relatively busy, although the traffic seemed to be mainly tourist traffic and there were very few lorries. It’s also inevitably pretty hilly: travelling through inland Toscana I counted on 1000 metres of climbing for every 50 kms I travelled. The reward for that climbing are big skies, views for miles and huge open spaces.
Map showing options
|Firenze to San Gimignano
|Firenze to Siena (direct)
|San Gimignano to Volterra
|Volterra to Siena
|Siena to Pienza
|Pienza to Radicofani
When to go
If you go in late-September and early-October you can enjoy the colours of the Autumn leaves in the vineyards, but elsewhere the fields will have been ploughed and the landscape is magnificent but a little austere. If you go in spring and early summer you can enjoy the spring flowers and the green of the wheat fields.
Bear in mind that in mid-Summer Toscana is hot, with temperatures well into the 30s in the hottest part of the day. Add into that the fact that the main tourist cities will be very busy crowded and it really isn’t the best time to be there. If you have the choice, go in late-Spring and early-Summer or early-Autumn.
The Chianti area is, of course, famous for the wine. Helped, perhaps, by the most memorable piece of product placement in movie history (16 second video - plays in overlay). The original Chianti was the area around Radda, Gaiole and Castellina who together formed an alliance for mutual defence. The league evolved and became increasingly occupied with the regulating wine-growing in the area - the role that it continues to play today. The cockerel was the symbol for the alliance.
The Chianti wine-growing denomination has expanded to take in most of central Toscana. However, only wine from the central area has the right to use the term Chianti Classico and use the black cockerel symbol.
For three centuries this area was the cockpit for the fierce rivalry, and almost continuous warfare, between Firenze and Siena - and in turn a theatre for conflict between factions within the Italian peninsula and France and Spain.
The Crete Senesi
The Crete Senesi is the name for the area to the south of Siena. While north of Siena wine is king, in the Crete the main crop is wheat and other cereals and the impression of the landscape is one of rolling hills punctuated by hilltop farmhouses often approached by a strada bianca lined with cypress trees. The Crete get their name from the local dialect word for clay. If you visit the area in late summer of autumn when the fields have been ploughed you’ll see the pale sandy brown of the crete. At times the landscape is austere but at the same time it has a certain grandeur.
The Val d’Orcia
The Val d’Orcia has been listed by UNESCO The Val d’Orcia is the area between Siena and Monte Amiata on the border with Lazio. The area has been given UNESCO world heritage status. According to the UNESCO website:
“The landscape of Val d’Orcia is part of the agricultural hinterland of Siena, redrawn and developed when it was integrated in the territory of the city-state in the 14th and 15th centuries to reflect an idealized model of good governance and to create an aesthetically pleasing picture. The landscape’s distinctive aesthetics, flat chalk plains out of which rise almost conical hills with fortified settlements on top, inspired many artists. Their images have come to exemplify the beauty of well-managed Renaissance agricultural landscapes.”
The area’s main towns include Pienza (also world-heritage listed), San Quirico d’Orcia, Montalcino and Montepulciano.
Coming to Firenze from the north the best option is probably the Ciclopista del Sole (eurovelo 7) which links Firenze with Bologna and leads north to the border with Austria.
After this tour you could continue on to Rome. But, never mind the old saying, there are other options: you could head west into Umbria, or you could link this tour with the Gran Tour della Maremma or the Grand Tour della Val di Merse (or both of them) giving you the opportunity to really get to know this region.
Maps to print out or view offline
About the maps
The maps are in two versions: A4 portrait format - for printing and maybe also for viewing on an iPad, and A5 for smaller tablets and smartphones. (A4 and A5 are international paper sizes).
Links open in new windows unless you ‘save as’ etc.
- Heart of Toscana gps files
(.zip file containing 3 gpx track files)
- Italy Points of Interest
POIs are like waypoints, but while you can usually only store a limited number of waypoints on a device, you can store thousands of POIs. These files include information about campsites and hostels, bike shops, train stations, drinking water sources as well as warnings for tunnels and roads where bikes are banned. Please check the ReadMe file for instructions. Updated April 2018. The file format is only compatible with Garmin GPSes .
Places to stay
There’s a good choice of accommodation along the way, and a good selection of campsites and hostels if you are on a budget, although as you get into the more sparsely populated south of the region, things can get a bit more tricky. However, there are lots of resources to help you find somewhere to stay.
terresiena.it (it/en) is an excellent site for travelling cyclists (although I’m not sure whether it has been updated recently). It includes an useful accommodation search facility. This lists the 141 places that have signed up to the tourist authority’s hospitality for cyclists scheme.
There’s an even more comprehensive searchable directory on terresiena.it (it/en) the main tourism website for the area. There’s a list of tourist information offices. look out for the brochure downloads for the individual areas within the provincia (equivalent to a county).
Find and book places to stay with Booking.com
Booking.com area pages:
About these links
If you use these links to book accommodation Booking.com will pay me a small part of their commission. This helps support the costs of producing this site.
I use Booking.com to find and book places to stay when there are no campsites in the area. The large majority of hotels and many hostels are now on ‘Booking’. I like it because it means that I can get almost-instant confirmation. The rating system is also a reliable guide to the quality of the accommodation.
I’ve never had a problem finding places to keep my bike —even if it’s a cupboard or store room. I always use the ‘special requests’ field on the booking form to tell the hotel that I’m travelling with a bike, which gives them the opportunity to let me know if there’s a problem.
Many properties offer free cancellation but it’s a good idea to check the conditions as these vary from property to property.
Hostels in Firenze:
- Hostel Sette Santi
- Ostello Gallo d’Oro
- Plus Hostel
- New Hostel
- Hostel Archi Rossi
- Locanda Rocco
- Academy Hostel
- Ostello Centrale
Campsites in Firenze
There are three campsites in, or near, Firenze:
- the Camping in Town Firenze (was Camping Michelangelo)
- the Camping Panoramico at Fiesole
- the Camping Internazionale Firenze
The Camping in Town Firenze is the most centrally-located with some beautiful views of Firenze and close to the Piazza Buonarotti from with a grandstand view over the city. It can be a bit noisy on the side nearest the road. The Panoramico offers views over the city that truly justify the name, but at the end of a long day, you may not relish the climb of the hill from central Firenze. the Internazionale is a fair way out from the city near the motorway. If you did opt to stay here your best bet might be to head for Impruneta and then pick up the Via Chiantigiana further on.
Transport and services
You can get flights to Firenze airport, but Pisa airport is the regions leading airport. It’s a shortish train journey from Firenze.
Firenze Santa Maria Novella train station is the main rail hub. There’s a train station at Certaldo with connections to Pisa, Firenze and Siena. There’s no station at San Gimignano.
Bike shops and bike rental
Tourist information websites
- visittuscany.com is the main tourist information site for the region (it/en/de/ru/pt/cn)
- terresiena.it is the excellent tourist information for the provincia di Siena which covers most of the route (it/en)
- firenzeturismo.it is the tourist information site for Firenze (it/en)