Published on: 2 February 2014 | Last updated: 7 January 2020
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 Bandiera Arancione (orange flag) status by the Touring Club Italiano.
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Map and altitude profile
Another fairly short section - but as is often the case in Italy, the key statistic is the amount of climbing.
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).
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.
The Piazza del Campo
The central piazza that hosts the annual Palio horse race. The piazza is big but you wonder how you could stage a horse race there. and why anyone in their right mind would want to be a jockey in the race.
With the Torre del Mangia, Siena’s major landmark and visible for miles around. One of the civic towers that was built in the middle ages by the comuni as expressions of civic pride and assertions of independence from Pope and Emperor. Siena’s at 88 metres is almost but not quite the tallest in Italy (it’s beaten by Bologna and Cremona). It’s called the Torre del Mangia after its first guardian Giovanni di Balduccio, who was nicknamed Mangiacquadagnior simply ‘Mangia’ because of his reputation as a spendthrift - literally translated the name means ‘eats earnings’.
You can climb the tower. (opening hours and ticket prices).
While you’re there, visit the Museo Civico. There’s lots of great art in Siena but if you don’t see anything else go here. Highlights include Sala del Mappamondo (Hall of the World Map), where you can admire Simone Martini’s Maestà (Virgin Mary in Majesty) (image opens in overlay). Picture from Wikimedia Commons (Google Art Project). On the other side of the room is another work attributed to Martini, a fresco of Guidoriccio da Fogliano, a captain of the Sienese army.
In the next room are the frescoes Allegories of Good and Bad Government by Ambrogio Lorenzetti. At the end of the room the central fresco shows Justice, Wisdom, Virtue and Peace on the walls on either side are contrasting scenes depicting (you’re probably ahead of me here) the results of good and bad government. The good depicts a sunlit, idyllic, serene city, with joyous citizens and a countryside filled with crops and a contadino (countryman) coming to town to sell his pig; the bad city is filled with vices, crime and disease. Sadly, the fresco of the results of bad government is in fairly poor condition.
Siena’s other must-see is the Duomo. For me the exuberant gothic façade is one of Toscana’s greatest sights. It’s certainly one of the greatest things you can see for free. But it’s worth stumping up for the admission to go inside. There’s the cupola by Bernini, statues by Donatello and Bernini, the exceptional mosaic floor, and the Libreria Piccolomini (Piccolomini library). The library frescoes, are by Pinturricchio - one of his assistants was the young Raphael (Raffaelo Sanzio). They celebrate the life of the young Enea Silvio Piccolomini who worked as a diplomat before going on to become Pope Pius II. Piccolomini was also responsible for the rebuilding of Pienza - his home town and birthplace as an ideal Renaissance city.
Cycling around Siena
From Siena you could head for Sovicille and the Grand Tour della Val di Merse. You could do this as a circuit and resume this tour as it heads for the Val d’Orcia, or you could link with the Gran Tour della Maremma which will take you all the way to the coast and back. These areas may not be as well known as the area between Siena and Firenze, but it has every bit as much to offer.
You could also do all or part of the Eroica signposted route which follows a 205-kilometre figure of eight to the south and east of the city.
Places to stay
Hotels and B&Bs
The website terresiena.it has a useful database of bike-friendly accommodation in the area.
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.
Transport and services
There are train stations at the Saline di Volterra down the hill from the main town, and in Siena.