Heart of Toscana: Part 5 The Val d’Orcia: Pienza, Radicofani and beyond

Published on:  | Last updated: 3 January 2020

The Val d'Orcia and Monte Amiata

The Val d’Orcia and Monte Amiata

This part of the tour takes you along another of Toscana’s great scenic roads in the Val d’Orcia, passing Montepulciano, and on towards the estate of La Foce one of Italy’s great gardens. From La Foce it climbs towards Monte Amiata and Radicofani with its iconic rocca (fortress) which for gener­a­tions of travellers was a key landmark marking the way to Rome.

 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. 

UNESCO: world-heritage listing for the Val d’Orcia

Map and altitude profile

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Note: You have lots of choices of route south - really it’s very hard to go wrong but if you are tempted to avoid the climb to Radicofani bear in mind that the Via Cassia is not only the dullest option, but there’s a long tunnel.

Route description

The route makes a bit of a detour on its way towards La Foce taking the scenic SP146 Chianciano road. There are more direct options, but this one has the best views (zoom in on the terrain map and you’ll see why). This round­about route also offers the possib­ility of a detour to visit Montepulciano - although there is a bit of a climb up to the town itself (just over 80 metres altitude gain). The road skirts the bottom of the hill, and turns to the right, at San Biagio, below Montepulciano, and a little after you need to turn off onto another strada provin­ciale (the SP88) this is an unsur­faced strada bianca for the next 7 kilometres. But if you are nervous about unsur­faced roads there’s no reason to panic: they are pretty well maintained, and smooth; the worst that’s likely to happen is that you may end up a bit dusty (in Siena you can spot the cars of the country people by the dust). If you have very narrow tyres and you really want to avoid this stretch then you can detour to La Foce taking the scenic road to Chianciano.

The strada bianca takes you to through the La Foce estate passing the Castelluccio medieval castle before descending to the villa itself. The estate was home to the Anglo-Irish-American author Iris Origo (and still is home to the Origo family). The Origos bought the estate in the inter-war years and began the process of restoring it, as part of this they called in the garden designer Cecil Pinsent. The gardens are open on Wednesday after­noons in summer and at weekends (opening hours and prices). This video (from the BBC series Monty Don’s Italian Gardens) will give you an idea of why they’d be worth a visit if you can fit it in with your tour plans.

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If the video gets taken down try a search on youtube. Oh and if you have a moment, please let me know.

Iris Origo was a writer and is probably best known for the book War in Val d’Orcia: An Italian War Diary 1943-44 (Amazon). It’s a moving account of the impact of the war on ordinary Italians and their courage in putting their lives at risk to shelter escaped Allied prisoners. War in Val d’Orcia is defin­itely on my ‘if-you-only-read-one-book-about-Italy-read-this’ list. If you are at all inter­ested in the area then you won’t regret buying it.

Here’s a small sample

As the front approaches, and all the neigh­bouring towns have been shelled and bombed, people gather in the house’s cellar and debate whether and how to escape. They decide to take the road for Chianciano and then cut across country:

 Each of the children carried his own coat and jersey. The grown-ups each carried a baby, or a sack of bread. And so, in a long, strag­gling line, with the children clutching at our skirts, half walking, half running, we started off down the Chianciano road.

I did not think, then, that we should get all the children through safely. We had been warned to stick to the middle of the road, to avoid mines, and to keep spread out, so as not to attract the attention of Allied planes. German soldiers, working at mine-laying, looked up in aston­ishment as we passed. ‘Du lieber Gott! What are those children still doing here?’ Some corpses lay, uncovered, by the roadside. A German Red Cross lorry came tearing up the hill, nearly running over us. And all the time the shells were falling, some nearer, some farther off, and the planes flew overhead. The children were very good, the older ones carrying whatever they could, the smaller ones stumbling along as fast as their small legs could carry them. Donata shouted with glee on Antonio’s shoulder. No one cried except the tiny babies, but now and again there was a wail: ‘I can’t go so fast!’ and someone would pick up that child for a few hundred yards. The sun was blazing overhead, the hill very steep, and none of us had had any food since early breakfast. But every stumbling, weary step was taking us farther away from the cellar, and from what was still to come.

After four hours we got to San Biagio, at the foot of the Montepulciano hill, and there sat down in a ditch for a breather before the last pull. We were very tired now, and a dreadful thought came over us: ‘What if the Braccis should have left?’ ‘What if we find no shelter here?’ But as we sat there, a little group of Montepulciano citizens appeared, then yet another: they had seen us from the ramparts, and were coming down to meet us with open arms. Never was there a more touching welcome. Many of them were partisans; others were refugees themselves from the south whom we had helped; yet others old friends among the Montepulciano workmen. They shouldered the children and our packages, and in a triumphant procession, cheered by so much kindness, we climbed up the village street, Antonio at the head, with Donata on his shoulder. Bracci and his wife Margherita came out to meet us, the children were at once settled on cushions on the terrace, and the Montepulcianesi vied with each other in offering accom­mod­ation. Antonio and I acted as billeting officers. Three went to one house, four to another, and the Braccis nobly took in not only our whole family, but all the refugee children as well. The Braccis’ mattresses and blankets, which had been walled up, were pulled out again and laid on the ground, the children (after a meal of bread and cheese) put to bed, and at last we were able to wash and rest. Only one child was the worse for the terrible exper­ience: Rino, who had a touch of the sun and suddenly fainted. Benedetta (sharing a bed with me) woke up, when I came to bed, to say: ‘We’ve left the bangs behind at last, haven’t we?’ and then fell into a twelve hours’ sleep. 

Iris Origo: War in Val d’Orcia: An Italian War Diary 1943-44

Look out for the Strada di Valdoresi one of the iconic strade bianche lined with cypress trees check out the the opening sequence of the video or this picture (opens in overlay) from this page. The best view is from the estate itself, from the road it’s obscured by trees and the turning is easy to miss.

The Strada di Valdoresi near the La Foce estate in the Val d'Orcia

The Strada di Valdoresi near the La Foce estate in the Val d’Orcia

From La Foce the road descends down to the river d’Orcia (324m) and then it starts to climb again to the village of Cortignano (460m) and continues to climb to just over 600 metres. There’s a great section here on a wild road following the ridge for five kilometres, with views for miles on either side, before joining the road to Radicofani, and the climb to the village itself (altitude: 814 metres?) 

If you want somewhere to eat or have something to drink there’s the DopoLavoro (literally ‘after-work’); this was the community centre built for the estate’s workers and their families. Today there’s a restaurant (a bit pricey, but good) and a nice bar where you can eat more economically.

The Rocca di Radicofani in the early morning mist

The Rocca di Radicofani in the early morning mist

The Rocca di Radicofani is open all day from 10:30 until 19:30 (or dusk). This is on the list of things that I missed, and wish I had known about, but from the top of the tower you can see for miles over southern Toscana and northern Lazio - possibly one of the best views in the whole of Toscana. Pictures on valdorciasenese.com

Ghinotto di Tacco the Tuscan Robin Hood

Radicofani was also the base for the brigante (outlaw/brigand) Ghino di Tacco in the latter half of the thirteenth century Italy. The Tacco family razed the castle in Torrita di Siena in 1279. They were captured by the comune di Siena in 1285, and Tacco’s uncle and father were executed in Piazza del Campo in 1286. However, Ghino and his brother were under-age and so were not executed. In 1290, Ghino seized the fortress of Radicofani on the border with the Papal State. Di Tacco would descend from his stronghold to ambush the travellers on the ancient Via Cassia, stripping them of almost everything, but being sure to leave them enough to survive and to offer them a banquet. He allowed students and poor people to pass without harm.

More about Ghinotto di Tacco

His most spectacular act was to go to Rome with 400 armed men to seek out the judge who had condemned his father and uncle, and who had become an influ­ential and well-known judge at the court of the Papal States. Di Tacco entered the Papal tribunal in Campidoglio and beheaded the judge and his head on his pike which he took back it back to Radicofani, where he exposed the scalp on the tower for a long time. 

Dante describes the judge as one of the Negligent seeking atonement in the second Circle of Purgatory. Which seems a bit rough: poetic justice I guess.

Boccaccio in the Decameron (which heavily influ­enced Chaucer’s Canterbury Tales) depicts him as a brigante buono (good brigand). He devotes an entire novella of the Decameron to him - the title gives you the story in a nutshell: 

Ghino di Tacco piglia l’abate di Clignì e medicalo del male dello stomaco e poi il lascia quale, tornato in corte di Roma, lui ricon­cilia con Bonifazio papa e fallo friere dello Spedale. 

Ghino di Tacco seizes the Abbot of Cluny, cures him of his stomach ailment and then releases him; the abbot, having returned to the Roman court, recon­ciles him with Pope Bonifazio who makes him Prior of the Hospice.

According to the the Decameron, Ghino kidnapped the Abbot of Cluny on his way back from Rome. The Abbot, suffering stomach trouble from the high-life in Rome was on his way to have detox at the thermal spa of San Casciano dei Bagni but instead ended up locked in the in the fortress of Radicofani, with only bread and dried beans to eat and Vernaccia di San Gimignano to drink. This dietary regimen ‘miracu­lously’ cured the abbot’s stomach pains, and the Abbot returned to Rome and convinced the Pope to grant a pardon to Ghino di Tacco for the murder of the judge, and to appoint him as a Knight of St. John and Prior of the Ospedale di Santo Spirito (Hospital of the Holy Spirit). The Pope in turn persuaded the Sienese to grant him a pardon.


The problem with cycling in Italy is that sometimes there are just too many choices. That’s certainly the case here. Radicofani was for centuries a staging post on the way to Rome and the Lago di Bolsena and Rome are an obvious choice here. But there are others. If you are aiming for Rome you could also head south-east towards Orvieto. If you want to explore more of what Toscana has to offer you could head for the town of Abbadia di San Salvatore or Pitigliano and then pick up the Gran Tour della Maremma. Or you could head for Umbria and the Lago di Trasimeno (turn off at La voce and head for Chianciano Terme, or take the SS478 from Radicofani to Sarteano and Chiusi.

More information

Places to stay

Hotels and B&Bs

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

The Comune di Radicofani has a list of accom­mod­ation options in the area.

There’s a small B&B at La Foce (the Palazzolo) if your budget will stretch that far.

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.



The closest campsites to the route are:

If you are heading for Rome the first campsites after Radicofani are at the Lago Bolsena - or altern­at­ively there are three campsites around Pitigliano - take a look at the maps on this site of Campsites in Lazio and campsites in Toscana for information. 

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

Transport and services


The main Firenze — Roma train line runs in the valley between via Chiusi and Orvieto.


The terresiena.it site has a section devoted to the Val d’Orcia

stradavinonobile.it (en/it) the site of the Strada del Vino Nobile di Montepulciano has lots of general tourist inform­ation for the Montepulciano area including an accom­mod­ation search facility.

La Foce is the host for Incontri in Terra di Siena Arts Festival in summer. The public­a­tions section of the lafoce.com website has lots of articles to download and there’s a nice short article on montepulciano.net

Articles in this series

Wine list in a bar in Toscana (the Dopolavoro at La Foce near Montepulciano)

Wine list in a bar in Toscana (the Dopolavoro at La Foce near Montepulciano)

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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