Heart of Toscana: variant Firenze to Siena direct

Published on:  | Last updated: 3 January 2020

Countryside between Siena and Firenze

Countryside between Siena and Firenze

Along the Via Chiantigiana from Firenze to Siena

If you’ve decided to head direct to Siena instead of San Gimignano and Volterra then instead of turning off after Panzano in Chianti you simply stay on the Via Chiantigiana continuing through Castellina in Chianti and Quercegrosso for a further 30 kilometres. See The heart of Toscana: Firenze - San Gimignano for the description of the tour as far as Panzano.

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Castellina-in-Chianti it is the heartland of the Chianti and one of the original comuni that came together to form the Lega del Chianti (the others were Radda-in-Chianti and Gaiole-in-Chianti). Italy has hundreds of place names that are some variant of castello and castellina to has a splendid rocca comunale (fortress), but the most inter­esting sight is the Via delle Volte (vaults) a street that runs along the inside of the old city walls which has gradually been built over by citizens seeking to make use of every bit of land within the walls. 

Castellina-in-Chianti: Via delle Volte. Picture by ‘Vignaccia76’ from: Wikimedia Commons

Castellina (574m) is the highest point of the route and from here, while it’s not exactly downhill all the way it’s pretty straight forward: there’s a descent down to Quercegrosso 10 kilometres further on. After that there’s a small climb and then 10 kilometres of salis­cendo (up and down) into Siena.

If you are planning to stay at the campsite you will need to turn off the route before you get to Siena itself. I’d suggest leaving your tent and stuff at the campsite and then head into town. The hostel is also close to the route and before you get to the centro storico.

Siena highlights

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.

Palazzo Pubblico

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.

Ambrogio Lorenzetti: the Effects of Good Government in the Countryside

Ambrogio Lorenzetti: the Effects of Good Government in the Countryside. (Siena Palazzo Pubblico). Source: Wikimedia Commons/Google Art Project

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.

Siena: Palazzo Pubblico

Siena: Palazzo Pubblico

More information

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.

  Campsites map:  HoT-campsites-map-show map in overlay    |    HoT-campsites-map-show map in new window 

Transport and services

Transport connections

There’s a train station in Siena.


There’s a section devoted to Siena on the terresiena.it

Siena Duomo

Siena Duomo

Articles in this series

Get in touch

Please get in touch if you find any errors in the information, or if there’s anything, good or bad, that you’d want other cyclists to know.

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