Heart of Toscana: Part 4 The Crete Senesi: from Siena to Pienza

Published on:  | Last updated: 3 January 2020

On the Via Lauretana between Pienza and Siena

On the Via Lauretana between Pienza and Siena

This section of the route heads from Siena to Pienza. Through the memorable landscapes of the Crete Senese and the Val d’Orcia. The Crete Senese 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 area’s main towns include Pienza (also world-heritage listed), San Quirico d’Orcia, Montalcino and Montepulciano.

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On the Via Lauretana between Pienza and Siena

On the Via Lauretana between Pienza and Siena

Route description

Leaving Siena

As with the ride from Firenze, the main challenge is to find a way over the major roads that pass to the west and south of the city. 

If you are leaving from Siena itself you need to head for the Porta Romana with its splendid crenel­lated double gateway left over from the old medieval walls. (If you are staying at the campsite then you may want to pick up the route a little later - see the gpx file in the download pack).

You then continue on towards for Le Ropole and then Arbia. From here the Via Lauretana (SP438) climbs out to the town of Asciano (177m) 27 kms from Siena. Asciano is your last chance for something to eat or drink.

This really is a great area for cycling and pretty much any road will give you a great ride. Which makes it a tough task to just picking one. Your choice may spend on where you are heading for.My suggested route takes heads for Pienza via Chiusure, Montisi and Castelmuzio. If you prefer, you have the option of heading from Trequanda on the road towards Montepulciano.

View of the Abbazia di Monte Oliveto Maggiore

View of the Abbazia di Monte Oliveto Maggiore

The Abbazia di Monte Oliveto Maggiore

One the major place of interest in the area is the Abbazia di Monte Oliveto Maggiore (it/en). This is a couple of kilometres off the route near Chiusure. The abbey is most famous for the Chiostro Grande (great cloister) with a cycle of frescoes depicting the life of Saint Benedict. The frescoes were begun by Luca Signorelli who did 9 frescoes on the west side and completed by Il Sodoma who painted a further 28.

Monte Oliveto Maggiore: fresco by Il Sadoma 'Le Male Femmine'

Monte Oliveto Maggiore: Le Male Femmine (the temptresses sent to tempt the monks)

The frescoes also include a self-portrait of Il Sodoma - who is pictured with a couple of pet badgers (image opens in overlay), completely upstaging the official subject of the fresco: Saint Benedict’s first miracle.

The Bosco della Ragnaia

At San Giovanni d’Asso there’s the Bosco della Ragnaia a woodland park and garden created by the American artist Sheppard Craige. this was something I didn’t know about when I passed through the area, but it seems like it might be an inter­esting stop. From the website:

 Under tall oaks one may find many inscrip­tions that gather moss while waiting to be noticed by a visitor. Some will be familiar, others enigmatic, while yet others merely express Sheppard’s sense of whimsy. Notable built features include: an Altar to Scepticism, the Center of the Universe, and an Oracle of Yourself. The Bosco does not offer a meaning, but is, on the contrary, open to all inter­pret­a­tions. 

There’s also also very short video trailer:

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Pienza was built by Pope Pius who decided that he was going to completely rebuild and remodel his home town as a model renais­sance city - and rename it in his own honour. It’s a lovely place to walk around. The main attraction is the Palazzo Piccolomini where the family lived until the 1960s when the the last count died without a successor, his son having died in the war. The loggia has a superb view towards Monte Amiata. The only problem is that there’s a rather tedious guided visit where you go round, stop, listen to the audio guide then continue to the next stop and listen to the next bit - and so on.

The Val d'Orcia and Monte Amiata see from the loggia of the palazzo Piccolomini

The Val d’Orcia and Monte Amiata see from the loggia of the Palazzo Piccolomini


Rather than heading for Pienza you could head towards Montepulciano and Chiusi where you can pick up the Ciclopista del Sole (eurovelo 7).

After the Abbazia di Monte Oliveto you could continue down the hill to Buonconvento and then head for Pienza, via Montalcino and San Quirico - a longer, but more scenic route than taking the main Via Cassia. You could even detour to another abbey the Abbazia di Sant Antimo (en.wikipedia.org).

The Ciclovia Francigena (until recently called the Ciclovia dei Pellegrini) passes through San Quirico, before heading for Radicofani.

The Val d'Orcia near Montalcino

The Val d’Orcia near Montalcino

More information

Places to stay

Hotels and B&Bs etc

The website terresiena.it has a useful database of bike-friendly accom­mod­ation in the area.

In Castelmuzio there’s the Locanda Casalmustia.

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.


Camping is a little trickier, but there are sites:

  • the Podere Il Casale near Pienza which is an agrit­urismo with a campsite. Breakfast is included in the price.
  • Il Treccolo at San Giovanni d’Asso. This is a site that I wish I had known about when I was in the area;
  • there may be a campsite near Montepulciano (the Agricampeggio Belmondo) but I would check firsts
  • the Camping delle Piscine at Sarteano is the largest campsite in the area
  • I’ve stayed at La Fattoria near Chiusi (which is also a hotel), but its Facebook page hasn’t been updated since 2016
  • I’ve also stayed at the campsite belonging to the Ristorante Pesce d’Oro at the Lago di Chiusi (the restaurant is excellent).

I stayed at the Podere Il Casale. There are superb views from the Podere towards the Monte Amiata. The owner of the agrit­urismo is a Swiss cheese­maker —as in a cheese­maker who happens to be Swiss, rather than someone who makes Swiss cheese (although he may also make Swiss cheese). There are also a couple of peacocks who act like they own the place.

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

Peacock from the Podere Il Casale

Peacock from the Podere Il Casale

Transport and services


There are train stations at Asciano and San Giovanni d’Asso, although your best bet may be to head for Chiusi on the main line between Rome and Firenze.


For general tourism inform­ation the terresiena.it has sections dedicated to the Crete Senesi and the Val d’Orcia.

The Ufficio Turistico has a website with an accom­mod­ation listing.

If you’re looking for a supported cycling holiday you might want to check out the website of Cicloposse who are based in Pienza and offer guided and self-guided tours as well as a cycling and cooking holiday

Articles in this series

Pienza (Toscana)

Pienza (Toscana)

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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