Heart of Toscana: Part 3 Volterra to Siena

Published on:  | Last updated: 9 February 2018

Countryside between Volterra and Siena

Countryside between Volterra and Siena

While the larger Tuscan cities like Siena and Volterra are deservedly big attractions, it would be a big mistake to ignore the smaller towns and villages. This section of the tour takes you to Casole d'Elsa and Monteriggioni – both have been awarded a Bandiera Arancione (orange flag) by the Touring Club Italiano and are included in their list of Best Small Towns in Italy.

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Another fairly short section – but as is often the case in Italy, the key statistic is the amount of climbing.

Route description

Coming out of the city you take the street that takes you past the hulking great fortress built by the Medici, which today is used as prison (Casa di Reclusione). It's best known as home to the renowned theatre company Compagnia della Fortezza (it).

As you come out of the gates on your left-hand side there's a plaque commemorating the liberation of the city in 1944 with a photo of the GIs coming up the street towards the gate.

There's then a descent past some glorious scenery, followed by a 9-kilometre stretch on the main road between Siena and Cecina this is relatively busy – but the road is reasonably wide and the views from the road are exceptional. You then turn off onto a much quieter, in fact practically deserted, road to Casole d'Elsa (402m) 11 kms further on at the 25-kilometre point.

Casole is a great place to stop for a break, but if you do nothing else, park your bike and climb to the top of the belvedere(viewpoint) for an exceptional view over southern Toscana. Casole also has its own palio which takes place on the second Sunday in July, for more information see ecomuseovaldelsa.org – Palio di Casole d‘Elsa.


The next stop is the walled city of Monteriggioni at the 45-kilometre point, a tiny village with an almost perfectly-preserved set of medieval walls. You walk along the walls and enjoy the views (opening times and prices).

Aerial view of Monteriggioni

Aerial view of Monteriggioni (Source: visittuscany.com)

Dante Alighieri used the towers of Monteriggioni to evoke the sight of the ring of giants encircling the Infernal abyss.

Show quotation and translation

 però che, come su la cerchia tonda
Montereggion di torri si corona,
così la proda che 'l pozzo circonda
torreggiavan di mezza la persona
li orribili giganti, cui minaccia
Giove del cielo ancora quando tuona. 

Dante Alighieri, Inferno canto XXXI, lines 40-45

 As with circling round
Of turrets, Monteriggioni crowns his walls;
E’en thus the shore, encompassing the abyss,
Was turreted with giants, half their length
Uprearing, horrible, whom Jove from heaven
Yet threatens, when his muttering thunder rolls. 

Translation Henry Francis Cary. Source en.wikipedia.org

The town also appears in the game Assassin's Creed II and Assassin's Creed: Brotherhood Monteriggioni as it appears in the Assassin’s Creed Brotherhood (image opens in overlay)Source: Assassin’s Creed Wiki.

When I visited Monteriggioni the first thing that struck me, after the view of the city walls, was the size of the nearby car park: in the peak tourist season it clearly attracts a lot of visitors.

From Monteriggioni there are 8 kilometres alone the Via Cassia to the Siena ring road. In complete contrast to the section at Certaldo, this is relatively quiet and scenic.

From the ring road the route follows the Ciclovia Francigena (until recently called the Ciclovia dei Pellegrini) (eurovelo 5) into the centre of Siena. Note that if you are planning to stay at the campsite it's probably best to turn off before the centre.

Siena: Palazzo Pubblico

Siena: Palazzo Pubblico

More information

Places to stay

Hotels and B&Bs

The website bici.terresiena.it has a useful database of hotels in the Siena area and other accommodation such as agriturismi and B&Bs. The places listed in the site offer additional facilities such as secure bike storage and tools.

Find and book places to stay with Booking.com

Booking.com pages for places on this section of the route:

 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.


There's a hostel in Siena (the Ostello di Siena/Ostello Guidoriccio). The Camping Siena Colleverde also offers 'bungalows' which may be an economical option if you are travelling as a group. There are lots of agriturismi in the area but bear in mind that prices will vary a lot and some may be self-catering apartments.

In addition to the campsite and hostel in Siena, there's a hostel in Strove on the Via Francigena. There's more information and pictures here (monteriggioniturismo.it – Sosta di Strove. Note that the hostel gives priority (and reduced prices) to pilgrims with a credential.


At Siena there's the very good Camping Siena Colleverde a little way out of town.

There's also another campsite near Monteriggioni, the improbably-named, Camping Luxor. This is on the other side of the motorway but accessed from the Via Cassia between Monteriggioni and Siena. Keep an eye out for the sign the turning is easy to miss.

  Map of campsites along the route:  HoT-campsites-map-show map in overlay    |    HoT-campsites-map-show map in new window   

Transport and services

Transport connections

There are train stations at the Saline di Volterra down the hill from the main town, and in Siena.


bestsmalltownsitaly.com for more about Casole d’Elsa and Monteriggioni. There’s a section devoted to Siena on the terresiena.it

Articles in this series

Siena Duomo

Siena Duomo

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