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Tourist guide to the castles and fortresses between Val d'Orcia and Amiata

A journey back in time ..... between monuments of the past and landscape views. Archaeological ruins, Romanesque parish churches, Aldobrandeschi castles, stone villages yet delightful with floral decorations and curious shops, health spas, luxuriant cultivations. A beautiful route in this area and its ancient villages rich in history and traditions.

The first certain news of the existence of a settlement in Arcidosso dates back to the year 860 and reports it as a possession of the Abbey of SS. Savior. The construction of the first nucleus of the castle, around which the town will develop, can be dated around the year one thousand. From the 12th to the 14th century it was a fief of the Aldobrandeschi counts and became an important military stronghold, an extreme bulwark against the penetration of Siena into the Amiatino territory.
The current appearance of the fortress is the result of several extensions undergone by the original 11th century Lombard construction; it consists of an imposing building with two buildings (one of which is lower), with a quadrangular section that rests, for most of the perimeter, on imposing shoe bases; the external walls are lined with filaretto.
The north side of the complex is characterized by the presence of a tower (Mastio) which rises above the roof of the highest building (Palazzo). The top of the tower is crowned by a series of blind arches resting on shelves, which form the basis of the battlements above. The fortress, recently restored, is now used as a space for cultural activities. From the top of the tower (paid ascent) you can enjoy a splendid panorama of the summit of Monte Amiata.
Three gates remain of the medieval walls, two of which are original: Porta di Castello and Porta Talassese (towards the sea). From here, going down towards Codaccio, you reach the Porta dell'Orologio, built in 1851 to replace the Porta di Mezzo.
Arcidosso rises at 679 m asl on the slopes of the western slope of Monte Amiata.

The origin of the Vignoni castle dates back to the 11th century, as a possession of the Abbey of S.Antimo
In the current fortified village you can still see a tower, now severed, with a strong and wide scarp and surmounted by a redondone and some small windows. This was the keep, the heart of the fort. Even one of the ancient access gates to the walled enclosure is still perfectly intact, next to the church of San Biagio. Outside the door the view of the Valdorcia is breathtaking, on the left stands the bell tower of the church and on the right the best preserved part of the walls, with the corner tower, built with the same characteristics as the keep.
San Biagio, of Romanesque origin although heavily remodeled inside, has a single nave with still remains of frescoes from the 14th and 15th centuries. From this church come the baptismal font (from 1585) currently in the Collegiate Church of San Quirico d'Orcia and the bronze crucifix by Giambologna now in the Museum of Montalcino.
The Borgo di Vignoni rises above the village of Bagno Vignoni, can be reached, along a dirt road, from San Quirico d'Orcia following the signs for Ripa d'Orcia / Vignoni.

3 - Rocca Aldobrandesca of Castiglione d'Orcia

The remains of what was once the mighty Rocca Aldobrandesca dominate the medieval village of Castiglione d'Orcia. The Rocca stands at the highest point of the 574-meter high to which the town is built, whose walls, in large tracts still visible despite the fact that numerous houses have sprung up against it, once connected.
The construction of the Rocca was due to the feudal family of the Aldobrandeschi of Santa Fiora, one of the most powerful in southern Tuscany, around the 10th century. The fort controlled the ancient road that from Mount Amiata leads into the Val d'Orcia through which the main communication routes to and from the Maremma passed. The proximity, practically a few hundred meters as the crow flies, of the equally powerful Rocca di Tentennano on the rocky spur of Rocca d'Orcia, severely limited the control that the Rocca Aldobrandesca could exercise on the Val d'Orcia and on the Via Francigena / Cassia who crossed it, as the 'twin' stood in a strategically better position for the purpose
The remains of the fortification are scarce, both for the state of neglect in which it was left since the end of the 'Siena War' of the 16th century, and above all for the serious damage suffered during the bombing of the last war. What remains of the keep shows us the excellent materials used in the construction and makes us imagine that as a whole the appearance had to be very close to that of a classic-medieval fortress palace, with an enclosure capable of containing the population in case of collapse of the city walls. The town has undergone a major renovation, including the repaving of the streets of the historic core.
The fortress overlooks the medieval village of Castiglione d'Orcia.


A first glance is enough to understand the reasons that led to the construction of the Rocca di Tentennano or Tintinnano: from the large limestone rock on the edge of the Val d'Orcia that hosts it, it was possible to check the path of the Via Francigena below and access to the Gorges of the Orcia through which the communication routes to and from the Maremma passed, relying on a virtually impregnable position.
The first reports that attest to the existence of a settlement called Tintinnano date back to the year 853. The fortification developed mainly during the years 1250-58, when it came into the possession of the Municipality of Siena.
The Rocca is also famous for having hosted Santa Caterina da Siena in 1377, which according to legend learned to read and write here thanks to a miracle.
The defense system of the Rocca is an integral part with those of the underlying village. A first circuit circuit (in part still visible today) enclosed Rocca D'Orcia and connected it to the Rocca. A second circuit enclosed the top of the rocky spur, which was accessed through a door of which only a few remains are visible. This was the external courtyard of the fortification, where several buildings stood, now disappeared.
At the north end of the courtyard a series of stairs leads to the heart of the stronghold: the Cassero. This consists of a pentagonal area enclosed by mighty ramparts which still retain part of the battlements. The access door to the Cassero was destroyed but it is still possible to reach the patrol walkway. From here, thanks to an iron staircase placed during recent renovations, a round arch door leads to the Torrione. The original access was via a wooden escalator, which was withdrawn in case of danger. The Torrione also has a pentagonal plan and two internal floors. Its function, in addition to that of sighting, was to lodge for the command and last defensive bulwark. The walls have a thickness of about three meters, detectable by the slits made in the masonry, and the internal rooms have splendid barrel vaults. The upper floor is particularly interesting, divided into two rooms, where you can see the mouth of a cistern that guaranteed the water supply and an oven built into the wall. The second room leads to the roof terrace. The view over the valley is magnificent from here.

Since the 11th century, the area of southern Tuscany around the Piancastagnaio castle was the subject of the expansionist policy of the powerful Aldobrandeschi family and the whole territory is rich in historical evidence related to their potentate.
Built on the slopes of Monte Amiata, the town has a circular shape, once enclosed by a fortified city wall interspersed with square towers and four doors. The walls have been almost completely demolished, today three towers remain visible, two semicircular and one square, the main door next to the fortress and three other, very simple, in the southern part of the walls' Porta Romana ',' Porticciola 'and' Porta di Voltaia '. The mighty Rocca Aldobrandesca still stands at the highest point of the town.
The building has a quadrilateral shape and is equipped with high walls with steep slopes. Two towers rise from the fence, the largest, both in terms of strength and height, had functions of formwork, the other, placed in the opposite corner, defended the underlying gateway to the city. The whole complex was equipped with a defensive apparatus to protrude on corbels, still almost intact today, and battlements mostly disappeared. The Rocca is in excellent condition thanks to a careful restoration work completed at the end of the last century.
Piancastagnaio rises on the slopes of Monte Amiata and can be reached by following Via Cassia until the junction for Abbadia S.Salvatore / Vetta Amiata / Piancastagnaio.

The fortress of Roccalbegna crowns a rock, simply called 'stone', which overlooks the homonymous village from a height of sixty meters. The town lies on the southern flank of Mount Labbro at the confluence of the Armancione and Albegna rivers, which has always been a key strategic point for controlling the road that crosses the area of Monte Amiata, which at this point narrows.
Just go up to the top of the 'stone', and look out from the ramparts of the medieval fortification to have an exceptional panoramic view over the whole valley.
The fortress that came almost intact to us was the minor fort, used essentially as a lookout point and last refuge in case of capitulation of the village. During the 14th century the town experienced a period of great degradation which caused its almost total abandonment. In 1455 the fortifications were readapted by the Sienese, but this only partially stopped the involutionary process of the area. With the defeat of the Sienese Republic, in the mid-16th century Roccalbegna passed to the Grand Duchy ruled by Cosimo I of the Medici, but already in 1560 it was given in fiefdom to Cardinal Antonio Sforza. Grand ducal fiefdom remained until 1751.
Roccalbegna dominates the valley of the Albegna river on the slopes of Mount Labbro, south of Mount Amiata. It is about 11 kilometers from Arcidosso, the main center of the area.

Rocca Silvana, also called Rocca Selvena or Roccaccia Selvena, today reduced to suggestive and still imposing ruins, was in the Middle Ages the most important palace-fortress in the area of Mount Amiata, being one of the main strongholds, almost certainly the richest, of the most powerful feudal dynasty of the time: the Aldobrandeschi. Its wealth was due to the nearby deposits of cinnabar and mercury exploited since before the year 1000 and its position at the top of a rocky hill, almost six hundred meters high, with three sides overhanging the valley of the Fiora river which it gave him almost impregnability.
As mentioned, the ruins of the fortress dominate the landscape and the trend of the double walls is still easily recognizable, the first enclosed the inhabited area and the second internal to protect the feudal palace, with a semi-trapezoidal shape. At the eastern vertex of the second circle, in correspondence of the main door, stands a splendid pentagonal tower which served as a formwork.
Immediately to the side of the tower, almost in the center of the second enclosure, there are the remains of the Palazzo del Signore, one of the highest examples of thirteenth-century stately home that we can find in Tuscany outside the large municipal cities. All around there are various remains of other buildings among which the cistern and the chapel can be identified. The complex remained in use until the end of the 17th century and then began its slow ruin, since after the exhaustion of the surrounding mines, what was its strength, its position as an eagle's nest difficult to attack and consequently also difficult to reach, it became his sentence.
The works that allowed the reopening of the site are part of the "Enhancement and use of the Rocca Silvana and Morone mine archaeological site" project, promoted by the Municipal Administration in order to create a synergic system between cultural heritage territorial.
This first excerpt of works has allowed the reopening of part of the summit area of the castle and interventions of arrangement of the fruition routes in the underlying mining area, still in progress.
The imposing ruins of the Rocca Silvana rise about a couple of kilometers outside the town of Selvena, along the road that leads to Sovana. It can be reached by following the SS2 Cassia until the junction for Abbadia S.Salvatore / Piancastagnaio

The ruins of the castle of Sassoforte rise on the top of the massif of the same name at more than 700 meters above sea level, immersed in a splendid forest landscape marked by beech and chestnut. It is certainly one of the most monumental architectural evidences of Tuscany, of which the imposing external walls, the refined noble residence and the well-stocked formwork, located at the highest point of the hill, are clearly visible. The site, used in the Etruscan-Roman age as a limit between the territories of neighboring cities, was built before the end of the eleventh century and was dominated by the Aldobrandeschi counts, which was succeeded by a powerful family of local lords, strongly linked to the Emperor Frederick II and at the Ghibelline deployment.
To the north-west is the formwork, a tall building still equipped with the access door (very narrow, about one meter) with a shelf decorated with a plant motif. Above this, there are two corbels which supported the defensive apparatus to protrude. In the remains of the internal rooms doors and slits can still be recognized, a water cistern is also identifiable, it is assumed that the manor house was located here.
In front of the walls there is a rectangular construction equipped with beautiful pointed windows and vaulted grafts.

All the details denote a great care, skill and refinement so much to identify a building of uncommon use, of considerable size and with infrequent structures in the area and certainly among the most remarkable in the area, testifying to the power achieved by the lords of Sassoforte . Given its position between the quarterdeck and the inhabited area, it was probably used as a public palace of justice.
The visit to Sassoforte is particularly suggestive for the centuries-old chestnut woods that you have to cross by going up the mountain on foot, for the sensation of gradual discovery that the various floors of the rhyolithic terrace give, for the truly exceptional panoramic views towards the sea and the hinterland.
The remains of Sassoforte can be reached from the town of Sassofortino. Take the Siena-Grosseto highway to the Civitella Marittima exit, then continue to Roccastrada and, beyond the town, to Sassofortino / Roccatederighi. Once in the village, follow the signs for the castle / sports field, at the first crossroads continue to the right, the road becomes unpaved and steeply rising, after a few hundred meters the path returns flat and almost in front of the first house, which we meet on the right, a dirt road starts (recently rearranged but closed to vehicular traffic by a chain) that crosses the chestnut wood up to Sassoforte. There are also wooden arrows with the inscription 'Sassoforte' but not very legible. The castle can be reached, always along a path in the woods, even from the Municipal Park.

The castle of the Rocchette di Fazio rises in the valley of the Albegna river. In the Middle Ages, the whole valley, especially the hills that were the watershed with the adjacent Fiora valley, was feuded by the Aldobrandeschi counts and consequently all the castles in the area passed under their control and were rebuilt or reinforced starting from the twelfth century. The origin of this castle is due to Count Bonifazio, called Fazio, of the Aldobrandeschi, future father of that Ildebrandino who in 1272 became the head of the branch of S.Fiora of the powerful family.
Recently the ruins of the entire summit area of the castle have been consolidated and equipped as a belvedere, with a splendid view of the valley from here. The remains of the formwork and the walls still testify to us how great, albeit for a short time, Rocchette di Fazio had importance.

The walls, built with a hexagonal shape during the thirteenth century to defend the primitive settlement of the Aldobrandesque Castle and a series of buildings including a cistern, the Palace of Justice and the Praetorian Palace, are still in several places still recognizable. Two access doors are well preserved. Near the castle stands the Pieve di Santa Caterina, currently deconsecrated, also dating back to the thirteenth century.
10 - Rocca and Walls of Monticchiello
The castle, or rather walled village, of Monticchiello, already a fief of the local Lambardi family, was massively fortified by the Sienese towards the end of the thirteenth century, when it became an important frontier stronghold. Monticchiello was the cornerstone of the defensive organization located on the eastern border of the Sienese countryside and for this reason over the centuries it was at the center of numerous war events such as assaults, destruction and occupations.
The whole system of fortifications was headed by the Rocca located at the highest point of the hill where the village stands. It was erected in 1260 and essentially remains only the mighty Sienese formwork (private property - not open to visitors) with escarpment walls and equipped with an apparatus to protrude on stone corbels (partially intact), the walls were connected. The latter, largely preserved, were equipped with a patrol walkway supported by stone corbels and interspersed with towers of various sizes, seven are still intact, five square in shape and two round with redondone and scarp flanking the only door of driveway access to the town (Porta S.Agata), with a beautiful sixth arch. Other posts are located along the perimeter of the walls.

Even the village inside the fortifications has kept its medieval features intact and walking through its narrow streets you can still breathe history. Significant emergence is the propositural church of Saints Leonardo and Cristoforo which still remains as a testimony to the heyday of the village, retaining many frescoes of the Sienese school dating back to the 14th and 15th centuries.

The mighty Rocca di Radicofani has stood for more than a thousand years, was named for the first time in 973, from the top of an imposing basaltic cliff of 896 meters, from which it dominates the whole territory between Monte Cetona, the Val d'Orcia and Mount Amiata. At his feet passed an ancient pass of the Via Cassia, then Francigena or Romea, and it was undoubtedly this that determined his birth and his history, which has always been inextricably linked to this road.
The primitive fortress has an almost triangular plan and is equipped with a mighty keep and today it is in good condition thanks to the restoration work carried out in 1929 (the keep was the subject of a complete reconstruction, with a very different shape than the original) . Inside the keep is now housed the museum with artifacts found during the archaeological excavations carried out during the recent restoration. Also interesting are the remains of the other sides of the oldest nucleus, with remains of corbels for the plumbing defense and the other corner towers. Around this takes place the first circle of the bastioned fortress built in beautiful cut stones, with four irregular sides, the subject of an important restoration work that has brought them back to their former glory. The fortress was later expanded to the north, being the south side already naturally protected by a strong escarpment, but no great traces of these walls remain, except for the corner ramparts alongside one of which opens the ancient gate of 'access. The two fortresses surround practically the entire basaltic cliff on different levels, making it almost impossible to reach the heart of the fortification from any side.
The castle has been restored with a Fio project worth over 9 billion. Since January 1999 the fortress has been reopened to the public, today it can be fully visited, including all underground walkways and shooting stations.

Park Museum Fortified City of Radicofani
Visiting Hours: 10.30-19.30 (open every day)
For information contact the Brigadoon Company: 331 4103303
The mighty Rocca or Fortress of Radicofani rises at the southern end of the Val D'Orcia, on a narrow hill between Monte Amiata and the border with Umbria and Lazio. It can be easily reached by following a deviation of the SS.2 Cassia. Radicofani is on the UNESCO 'World Heritage Site' list as part of the 'Val d'Orcia Artistic and Cultural Park' and 'Orange Flag' of the Italian Touring Club.


The Castello del Potentino is located outside Seggiano. The castle was built around the year 1000 as an ancient possession of the bishops of Chiusi, whose diocese extended, at the time, to the whole area of Mount Amiata. In the eleventh century there is the attestation that belonged to the Visconti di Campiglia. In the thirteenth century it passed under Sienese control and belonged to the families of the Bonsignori, the Tolomei, the Salimbeni and the Bindi. Later, its importance as a border fortress had ceased, it was transformed into an elegant holiday resort and was purchased first by the Mignenelli family and then by the Venturi family. Enrico Venturi by testamentary disposition donated it to the Hospital of Santa Maria della Scala in Siena.
In 1600 it was bought by the Marquis Giovanni Battista Bourbon Del Monte who maintained it for centuries and only in 1906 sold it to the Swiss citizen Hemmeler. Today the complex is the heirs of the British writer Graham Greene who transformed it into a renowned farm.
The Castello del Potentino still has its original medieval appearance, occupying two distinct areas; the first, more external, includes the various annexed rural buildings and introduces the second, more internal area, which is accessed through an arched door that opens along a curtain wall equipped with top battlements.

The main area is made up of the castle itself which is L-shaped around a courtyard. The building, unlike the remaining complex, is in Renaissance style following the interventions carried out by the Sienese between the fifteenth and sixteenth centuries, with the architraved access door surmounted by a noble coat of arms; on the roof there is a small bell tower. Beyond the main area there is a third area which is quite distinct where there was an Italian garden, now completely scaled down and modified.
At the castle settlement, there is the noble chapel dedicated to Saint Anthony of Padua. The estate has now been revitalized and is dedicated to the production of wine, grappa and oil thanks to the 4 hectare vineyard and a suggestive olive grove.
It is possible to make tastings with a historical tour of the Castle and the Cellar, to learn about the winemaking process from the vine to the bottle and end with a taste of what makes Potentino so special. The visit lasts about 90 minutes. Tasting of 6 wines and grappa included.
The tastings must be booked in advance. Our guests can ask us directly or connect to the site:


The castle is undoubtedly the best known monument of the municipality of Roccastrada if not of the Upper Maremma, for its importance as a historical document (it is depicted in the famous fresco 'Guidoriccio da Fogliano at the siege of Montemassi' of the public palace of Siena attributed to Simone Martini) and for the high example of Gothic architecture it represents. The fortification, which crowns a hill 280 meters above the town, is made up of remains of the two pre-eminent buildings, to the north is the Palazzo / Mastio with the base of the scarp wall with numerous windows with large openings that denounce its residential function. and not strictly military, remains of a polygonal tower.
Inside the Palace you can still see the traces of the beams where the wooden floors rested, however subsequent to a vaulted ceiling whose remains are evident. A large water cistern was attached to the building, still plastered with lime today. To the south we find the remains of a quadrangular tower, equipped with slits, with leftovers of masonry vaults and well-worked corbels.
The historic center of Montemassi is very picturesque for having still retained the appearance of a compact "pine cone" village even though there are no traces of the walls, largely incorporated in the houses, except for a door, which once protected it and they connected to the castle.
The castle of Montemasi rises in the municipality of Roccastrada in the province of Grosseto, on a hill at 280m. above sea level on the edge of the northernmost part of the Grosseto plain