7.3 Hermitages and castles

From Porta Fontebranda to the slopes of Montagnola

The houses, fortunately, are only two or three storeys high, and the people at the windows look as if they are weighing them down lest they should all at once slide down towards Porta Fontebranda, through which they would certainly not pass, being so narrow. The streets of the city look at these almost as if they were about to descend upon them, with the cathedral in the centre and San Domenico above the yellow tufa. But Fontebranda is driven deep into ground, and the abattoirs stand tightly together on the crag that holds half of Siena.
(Federigo Tozzi, Bestie)

Porta Fontebranda is located at the lower part of the city, where a modest opening, certainly a ‘minor gate’ when compared to the other more imposing and majestic ones, creates an opening in the last of the city walls; beyond lies the countryside. Overhead, the imposing bulk of the Basilica di San Domenico rises majestically from the Poggio di Camporegio; on the hill in front, along a steeply inclined slope, the houses of the city descend haphazardly into the valley, clinging to each other as if to prop each other up, dominated by the monumental construction of the Duomo.

From this gateway you will begin your journey to visit mighty castles, isolated medieval villages, and splendid Romanesque churches. Pedal slightly downhill until you come to Strada di Pescaia, a busy arterial road which is not really suitable for cyclists. Ride uphill for about a kilometre and then take Via di Collinella and Strada dei Cappuccini on the left, still going uphill, and along which you can admire ‘Casa Rossa’, the ‘Poggio a’ Meli’ farmstead from Federigo Tozzi’s novel Con gli Occhi Chiusi, where the Sienese writer lived for a few years. At Palazzo Diavoli, take the road that leaves the outskirts of Siena behind and continues in the direction of Florence.

The Strada del Petriccio e Belriguardo, which you will come to on the left shortly after Braccio, is a continuous succession of ups and downs until you reach Pian del Lago, at the foot of the Montagnola Senese, a chain of hills that surrounds the city of Siena to the west in a green embrace of dense woodland and which were chosen by those seeking to live a hermit’s life during the Middle Ages. Two important Augustinian hermitages bear witness to this quest for the absolute, the Hermitage of San Salvatore di Lecceto and the Hermitage of San Leonardo al Lago, both immersed in the thick woods of oak and holm oak (Silva lacus) on the edge of the plain known as Pian del Lago, a marshland until the 18th century.
To reach the Lecceto hermitage, you have to turn off the SP 101 Montemaggio road and ride along a steep dirt track for just one kilometre (signposted ‘Lecceto’). The effort is more than compensated for by the beauty of the religious complex and the natural environment in which it is situated. There is also a picnic area.

After Lecceto, proceed towards the Hermitage of San Leonardo al Lago, which can be reached by turning back along the same unpaved road from before (there is also a shorter alternative route, but it is very uneven and runs entirely through the woods). Once back on the asphalt, veer left for about two kilometres and then left again. The road, which soon becomes unpaved, leads downhill as far as an old tavern, L’Osteriaccia, near which there used to be a mill that was fed by the waters from Pian del Lago, but where, in more recent times, as the name suggests, food and drink was served and where it was most likely also possible to sleep.

From here, two paths lead into the woods: one, on the right just before the building and indicated by a ‘Via Francigena’ sign, leads to the Piramide and the Canale del Granduca, two important architectural constructions that hark back to the reclamation of the area in the 18th century; the other, at a small fountain, to the left of L’Osteriaccia, leads to the hermitage along a path that dates back to the Middle Ages, as is evident from some sections of paving.

From San Leonardo al Lago, following a downhill dirt road, you will reach the SP di Montemaggio (turn left), and then a paved road where you should follow the signs for ‘Celsa.’ A short climb and then, at the first turnoff on the right, pedal along a dirt road that will lead you to Santa Colomba in less than a kilometre (you may have to put your foot on the ground in places). Santa Colomba is a small medieval village whose castle was seriously damaged in 1364 when the Compagnia di Ventura of Giovanni Acuto (John Howkwood), an English mercenary leader in the service of Florence, passed through. The church and a defensive tower, later used as the bell tower of the same religious structure, remain from that period. Other remains of medieval walls can be seen in the foundations of the grandiose villa that now dominates the town.
However, the most imposing structure is Villa Petrucci (15th–16th century), a building resulting from the renovation of an old manor house, most likely designed by the Sienese architect Baldassarre Peruzzi. The history of the villa was turbulent, and the constant raids of soldiers of fortune reduced it to such a precarious condition that in the early 1500s it was sold to Pandolfo Petrucci, at the time an eminent lord of Siena (some even called him a golpista, a coup leader), who transformed it into a villa.
In addition to the interesting exterior architecture, the interior of the palazzo features one of the most famous spiral staircases in Italy, along with that of the Belvedere in the Vatican, most likely the work of Baldassarre Peruzzi himself.
To return to Siena, you will need to ride downhill towards Pian del Lago, pedal for about three kilometres on the plain (on your left, on the hillside, is the unusual Castello della Chiocciola), and then follow the signs for the city, which is about five kilometres away.

Porta Fontebranda
Porta di Fontebranda is characterised by a very basic form of architecture, devoid of a bulwark and with a round arch on top of another lowered arch, above which is mounted the monogram of San Bernardino (which can be found on many palazzos, churches, city gates, and on the façade of Palazzo Pubblico: it is said to protect Siena from evil, following the Sienese appealing to the saint in 1630 to prevent the plague—the one known from the writings of Manzoni—from striking the city, and indeed it didn’t). Actually, until the 19th century, above the archway of the gate stood a turret with a covered loggia and bertesche, not too dissimilar from that of Porta Tufi and which is visible in various iconographic sources. Next to the gate stood the casotto dei dazieri (tollhouse), which has now disappeared but whose chimney remains embedded in the boundary wall. It was first mentioned in 1230, when restoration work was being carried out, testifying to the extent to which the municipality felt the need to enclose the important fountain bearing the same name within the walls. Around the middle of the 13th century, other expenses were recorded, especially for the construction of the wall that went up along the Costone.

Palazzo Diavoli
A building with a peculiar shape, near which one of the many battles between the Sienese and the Florentines took place in 1526, with victory going to the former. But how did Siena win?


Legend has it that the enemy troops had such frightening ‘demonic visions’ inside this odd structure that they had to flee;

this episode gave rise to the ‘sinister’ name of the brick building, which nowadays has a truly unusual shape; its oldest part dates back to the 14th century and was later elevated and fitted with a cylindrical tower. The chapel, now the Oratory of Santa Maria degli Angeli (St Mary of the Angels), dates back to the early decades of the 16th century and was built at the behest of the Turchi family, to whom the expansion of the building is also credited. The design of the chapel was initially attributed to Francesco di Giorgio Martini or Antonio Federighi, two great architects of the time, although recent studies suggest that it was built by local craftsmen and designed by the great Baldassarre Peruzzi.

Hermitage of Lecceto


It is said that Lecceto was established by a group of hermits who chose this site, then little more than a den of brigands and thieves, to make it a ‘nest of sanctity’. Some believe that this is one of the probable explanations for its motto: Ilicetum vetus Sanctitatis Illicium (‘the ancient Lecceto allurement of sanctity’). Hermits are said to have lived in the tufa caves that surround the Selva di Foltignano, or Selva del Lago, since the 11th century, and that they consecrated their small church in 1228, the first nucleus of communal life and of this Hermitage. The 14th and 15th centuries saw its greatest architectural, literary, and religious splendour, owing in part to its then prior, Blessed Filippo Agazzari (1398–1422). Tradition has it that St. Catherine herself frequented this place and was bound by deep friendship to a number of Lecceto friars, in particular the Englishman William Fleete, who was her spiritual father for several years as the small chapel dedicated to her next to the church reminds us today. The presence of Augustinian friars was suspended as a result of the Leopoldine suppressions of the early 19th century.

Hermitage of San Leonardo al Lago
The Augustinian hermitage of San Leonardo al Lago, first documented in 1119, was built near Lake Verano, the present-day Pian del Lago, as its name suggests. The first records date back to 1112 and testify to the presence of a hermit community, but the community’s existence would seem to have preceded that date. The hermitage became the property of the Augustinians in 1239 and, in 1250, a papal bull declared it united with San Salvatore di Lecceto. The presence of notable local religious figures, including the Blessed Agostino Novello, who spent the last years of his life there before dying in 1309, helped transform San Leonardo into a pilgrimage destination. The remains of the city walls and two towers, one round and one square, indicate that the hermitage was fortified in 1366 to provide shelter and hospitality to the nearby inhabitants of Santa Colomba in times of war. The architectural development of the monastic complex reflects the adherence of the first hermits to the Augustinian order: a quadrangular layout with buildings arranged around the cloister.



The monastery experienced a period of great prosperity through donations of land and offerings from the devout, as well as the direct intervention of public institutions such as the Ospedale di Santa Maria della Scala and the Republic of Siena, which promoted its renewal. In the 14th century, the original Romanesque church was enlarged, and a new Gothic one was built, with a single nave divided into three bays and a rectangular apse. The choir was entirely frescoed by the renowned Sienese painter Lippo Vanni, with a cycle dedicated to the life of the Virgin. The apse, among other things, is unusual: only female figures, including the Virgin Mary, are depicted, while the ceiling is frescoed with perhaps the first choir, complete with musical instruments of the time. In the former refectory, one of the masterpieces of 15th-century Sienese painting, there is a fine fresco of the Crocifissione (Crucifixion), although fragmentary, by Giovanni di Paolo del Grazia, painted around 1445.

It is possible to visit the complex from Tuesday to Sunday, from 9.30 a.m. to 3.30 p.m.; simply ring the caretaker who will accompany you and recount interesting stories that you will not find in any books.

BOX: Pian del Lago Land Reclamation and the Galleria del Granduca
It is known as the Piramide (Pyramid), the obelisk that commemorates the 18th-century reclamation of Pian del Lago. The Piramide also marks the beginning of the Canale del Granduca, a tunnel roughly two kilometres long that provided for, after several unsuccessful attempts, the outflow of water.


The Canale del Granduca was built to drain the waters of Pian del Lago, which during the winter would cover 156 hectares with a depth of up to 3 metres, while during periods of drought they formed a perennial lake of 93 hectares, thus giving its name to the wentire plain. The expansion and withdrawal of the water caused organic substances, grasses and insects, to rot, making the surroundings unhealthy, especially during the summer. For this reason, the friars from the nearby monasteries of San Leonardo al Lago or Belriguardo moved to the Certosa di Pontignano in summer, and would return to their monasteries in winter. The land surrounding the lake was also left uncultivated and abandoned, as the farmers could not live there because they would fall ill. Disease spread as far as the Augustinian convent in Lecceto, and as far as the villages of Celsa, Santa Colomba, Fungaia, Fornacelle, Chiocciola, and Abbadia a Quarto. So it was that in 1777 Grand Duke Pietro Leopoldo decided to act, commissioning the engineers Anastasio Anastasi and Bernardino Fantastici to visit the area and propose suitable interventions. The decisive push came from one of the most eminent figures of the time, Piero Ferroni, who was entrusted with the management of the works. Thanks in part to the mathematician’s efforts, work was completed on the restoration and rectification of the underground canal (hence the name of the Grand Duke) in which the engineer Agostino Fantastici also took part. The reclamation of this large area was brought to a successful conclusion in 1780.

Castello della Chiocciola
The name ‘Chiocciola’ (snail) probably derives from the helical staircase (spiral, in fact) that was built inside the cylindrical tower where the steps become lower and lower as they ascend, thereby reducing the fatigue of those who walk up it. The basement houses a cave where at the beginning of the century a number of prehistoric artefacts dating from the Neolithic period were found, some of which are preserved in the British Museum in London.


The oldest part, the castle, dating back to the 14th century, served, together with the nearby fortresses of Riciano, Strove, and Monteauto, as a defensive outpost to protect the Republic of Siena from enemy attacks; the villa next to the castle dates from the 19th century. The Chiocciola also owes its notoriety to a military event: it is said to have resisted the attacks of a battalion of one thousand infantrymen and one hundred Austro-Spanish cavalrymen at the time of the war of Siena in 1555, and to have surrendered with the honour of arms upon payment of 700 gold scudi. Among the various owners were the Brancadori counts, and it is said that a member of this family, in the mid-19th century, gambled away the castle during a night of idleness and libations, passing it into the hands of the Englishman Mister O’Brien.


I Comuni di Terre di Siena