8.6 Ora et Labora (Pray an work)

Benedictine Monasticism in Siena


During the Middle Ages, before the emergence of the mendicant orders, religious life in Europe was mostly Benedictine. In A.D. 529, St Benedict of Norcia founded the Abbey of Monte Cassino where, a few years later, he penned a Rule in which he outlined the precepts of monastic community life: the key concepts were stabilitas loci, i.e. the obligation to reside permanently in the same monastery (as opposed to the then rather widespread roaming of monks or self-styled monks) and conversatio, i.e. good moral conduct, mutual charity, and obedience to the abbot. Daily life was organised around prayer and work, alternating under the motto ora et labora (pray and work). At the same time, the Opus Dei (Work of God), a daily choral prayer recited by all, was supported by lectio divina, an intimate moment of meditation by the monk on the word of God. 

A few decades after St Benedict’s death in 547, the Abbey of Monte Cassino was destroyed and not rebuilt for a long time thereafter. The monastic community and the Benedictine tradition seemed to have disappeared. However, copies of the Rule had survived in the Roman libraries so that, around the end of the 6th century, Pope Gregory the Great praised the Rule and its author, thus increasing their popularity. The Benedictines gradually began to spread throughout most of Italy and Europe until, in period 816-17, an important synod declared the Rule of St Benedict binding for all monks: hundreds of monastic communities observed the precepts of the saint from Norcia, and monasteries became both centres of religious life and seats of cultural and economic development.


credit @poggiarello


The oldest Benedictine settlement on Sienese territory is the Monastery of Sant’Eugenio. It was founded in the Lombard era, in 730, at the very time when the monasticism of St Benedict began to flourish with increasing speed. Situated a few kilometres from the city, it was erected on land donated to the monks by the Castaldo (official) Regio Warnefrido and over the centuries underwent restoration work that altered its original architectural layout. Abandoned by the monastic community in 1786 and then suppressed in the 19th century, all that remains of the original complex are the church, the two cloisters—the main one in Renaissance style—and a small 16th-century chapel with a vault frescoed with grotesques. The church, also extensively remodelled with the demolition of the bell tower and the restoration of the brick façade, is characterised externally by a cylindrical tiburium enclosing the cupola. Inside, there is a rich and heterogeneous series of paintings dating from the 15th to the 17th century by artists such as Benvenuto di Giovanni, Il Riccio, and Il Sodoma.

Not far from the Monastery of Sant’Eugenio is the Benedictine Monastery of Saints Abbondio and Abbondanzio, also known as the Monastery of Santa Bonda, founded in 801. Now privately owned, the original Romanesque structure can be seen in the architectural remains of the church, traceable in the semi-circular external apse with a tufa wall and ornamental motif of hanging arches. A place of high spirituality in the medieval period, the monastery was frequented by St Catherine and Blessed Colombini, a Sienese contemporary of the saint and founder of the Jesuates Order who was interred here for some time.


At the beginning of the 14th century, a new Benedictine monastic movement came into being, founded by Saint Bernardo Tolomei, another religious figure of extraordinary importance to whom the city of Siena, alongside St Catherine and St Bernardine, gave birth. Heir to one of the city’s most powerful noble families, he was born in 1272 and was baptized with the name Giovanni. He studied law and, while still very young, became a professor of jurisprudence at Siena’s prestigious university. It was the Dominicans, who had already been present in Siena for years, who instilled in him an authentic faith and a great love for charity and prayer, virtues that would accompany him throughout his life. At the age of forty, suffering from blindness, he promised to devote himself to religious life if he recovered his sight, which miraculously he did. Thus, together with a number of companions who were also of noble origin, he withdrew to Accona, a desolate family land about thirty kilometres south-east of the city, to live as a hermit in the caves where he devoted himself to prayer, manual labour, and penance. A few years later, in 1319, urged by the Bishop of Arezzo to establish his community, he obtained a decree of construction for the future monastery, to be established under the rule of St Benedict, and thus gave life to the Congregazione di Santa Maria di Monte Oliveto (Congregation of St Mary of Mount Olivet), the name of which reveals his devotion to the Virgin Mary with a reference to the Monte degli Ulivi (Mount of Olives) in Jerusalem, the place where Christ prayed and was captured before the Passion, as well as his Ascension. Following the Benedictine Rule, he took the name Bernardo in honour of the great Cistercian Abbot Bernard of Clairvaux and abandoned the primitive hermitic choice for the adoption of communal life, although the monks wore a white habit instead of the Order’s traditional black one, out of the desire to honour the Blessed Virgin Mary that continues to characterise the spirituality of the Congregation today. The other peculiarity of the Olivetans was the temporary nature of the office of abbot, which, instead of behind held until death, lasted only one year. Bernardo refused to be appointed abbot at first, as he did not consider himself worthy, but then the monks, as evidence of his exceptional character, elected him for twenty-seven years in a row, appointing him to that office from 1321 until 1348, when the plague brought his life to an end at the Monastery of San Benedetto ai Tufi, also known as Monte Oliveto Minore, just outside Siena. Before his death, in addition to the monastery of Monte Oliveto Maggiore, the original motherhouse, he had founded ten other monasteries and, in 1344, obtained from Pope Clement VI the canonical approval of the Congregation.

Venerated while he was still alive, Bernardo soon received public recognition of his holiness and was considered blessed by the Olivetan Congregation from the time of his death. In 2009, following a lengthy cause of canonisation, he was proclaimed a saint by Pope Benedict XVI.


Immersed in the peace of the magnificent landscape of the Crete Senesi with its striking gullies, in the loamy area once called the ‘desert’ of Accona, the abbey’s first stone was laid in 1319, although construction continued over the centuries. It is an articulated and imposing complex, built entirely of red bricks, accessed by a drawbridge and a medieval building, used as a fortified gateway, and crowned by a quadrangular tower with battlements at the top. It has the classic layout of Benedictine abbeys, with a main cloister as well as other smaller ones, a church, a chapter house, and a refectory. The heart of the monastery is the large cloister, a place that symbolically indicates monastic life itself as communion with the brethren and with God: all the other rooms can be accessed from here, and the absence of a roof serves the purpose of maintaining physical contact with the sky, and therefore with God. The walls are painted around the perimeter with scenes depicting stories from the life of St Benedict. Painted between 1495 and 1505 by Luca Signorelli and Giovanni Antonio Bazzi, known as Il Sodoma, they represent one of the most important examples of Italian painting of the late Renaissance. Next to the cloister stands the church, built in the 15th century but renovated in Baroque style in the second half of the 18th century. The interior, in the shape of a Latin cross, is a dazzling treasure trove of works of art, including the wooden choir, carved and inlaid between 1503 and 1506 by Fra’ Giovanni da Verona, an Olivetan monk who lived for some years in Monte Oliveto and who created this masterpiece, part of which was later placed in the Cathedral of Siena. Composed of stalls or seats joined together, the choir is a typical element of monastic churches because it is used for the monks’ common prayer or Opus Dei, an essential moment in the life of the monastery. Friar Giovanni also designed the monumental library, a fundamental place in the Olivetan tradition, built in the Renaissance style, with three naves divided by columns with pietra serena capitals. It houses manuscripts and incunabula of rare value.

Always a centre of extraordinary importance, still inhabited by a large community of monks, the Abbey of Monte Oliveto Maggiore is the motherhouse of all the Olivetan communities in the world and its abbot is Ex Officio Abbot General of the entire Olivetan Benedictine Congregation. Its emblem is a three-peaked mountain, with a cross above the central one and an olive branch above each of the two mountains on the sides.


A few years after the foundation of the Abbey of Monte Oliveto Maggiore, Saint Bernardo Tolomei founded the Monastery of San Benedetto a Porta Tufi, also known as Monte Oliveto Minore, which was therefore the first daughter of the motherhouse.

credit louis-garden

Suppressed in 1808 and then destroyed, it was located along today’s road leading to the Camposanto della Misericordia, just outside the city walls of Siena, in a setting that reflects the very essence of Olivetan spirituality: solitude and prayer, but also charity and hospitality towards pilgrims and the needy. The historical importance of this place in the life of Siena at the time was considerable as it represented the link between Monte Oliveto Maggiore and the city’s culture. In addition, St Bernardo spent the last year of his life there caring for the sick during the Black Death of 1348. Although he himself was killed by the disease and his body was never found, having been thrown into a mass grave, as was the case with all plague victims, the monastery was regarded as his tomb by those who worshipped him, and the cult began to spread soon after his death.

The church was completed in the second half of the 14th century, while the construction and extension of the rest of the complex continued until the end of the 15th century. The importance of this monastery is also revealed by the extraordinary quality of the works of art that sources report had once been housed within, created by important artists and now dispersed in various locations. Among these is the sculptural group depicting the Compianto su Cristo Morto (Lamentation over the Dead Christ) by Francesco di Giorgio Martini, now in the church of Saints Niccolò and Giacomo in Quercegrossa, Beccafumi’s painting of the Stimmata di Santa Caterina (Stigmata of St Catherine), now in the Pinacoteca Nazionale di Siena, and the choir stalls by Fra’ Giovanni da Verona, relocated to Monte Oliveto Maggiore, the motherhouse.


The cult of St Bernardo is particularly linked to the town church of San Cristoforo, which stands in the centrally located Piazza Tolomei, dominated by the powerful family’s palazzo of the same name, an elegant example of 13th-century civil Gothic architecture. The church was built between the 11th and 12th centuries and its importance is documented in medieval documents that mention its use for meetings of the Consiglio Generale del Comune (General Council of the Municipality). While the oldest vestiges can be seen in part of the outer perimeter walls and in the apse, the church’s current appearance is due to its renovation at the beginning of the 19th century, following damage to the building in the terrible earthquake that struck the city in 1798. It was the Tolomei family who financed the rebuilding of the neoclassical façade, now made of brick but originally covered in plaster, in keeping with the taste of the time. The façade is marked by half-columns supporting a tympanum with entablature, and has two niches at the sides, inside which stand sculptures by Giuseppe Silini depicting St Bernardo and the Blessed Nera Tolomei, another religious figure in the family, a Dominican tertiary like St Catherine. Bernardo holds a skull in his hand, a symbol of the rejection of the pleasures of life typical of penitents and hermits and an allusion to the first phase of his spiritual experience in the desert of Accona. The artistic heritage of the church, many of whose works are now kept in the nearby Museo Diocesano d’Arte Sacra (Diocesan Museum of Sacred Art), also includes the sculptural group of the high altar depicting the Transito di San Benedetto (Passing of St Benedict), created at the end of the 17th century by Giovanni Antonio Mazzuoli for the Olivetan Monastery of San Benedetto ai Tufi and moved to its current location following its suppression.


The Olivetans were not the only Benedictine presence in the Sienese territory. In 1039, St John Gualbert, a monk at the Benedictine monastery of San Miniato in Florence, after having accused his abbot of simony (buying and selling ecclesiastical offices), retired to the nearby woods of Vallombrosa and, together with two other monks, founded an abbey, giving life to a new form of monastic observance that combined the austerities and penances of hermit life with living together with fellow monks. The fundamental point of divergence from the Benedictine rule was the prohibition of manual labour in favour of an existence entirely dedicated to prayer and pure contemplation, which led to the unprecedented introduction of lay brothers, called converts, into the monasteries to perform such tasks exclusively. The Congregazione di Vallombrosa (Congregation of Vallombrosa) was approved by Pope Victor II in 1055.

The presence of the Vallombrosian monks in Siena, documented from the first half of the 12th century, is linked to the Abbey of San Michele al Monte di San Donato, better known as Abbadia Vecchia (Old Abbey), located a few steps from what is now the city’s main thoroughfare. All that remains of the complex is the church, which, with the exception of the octagonal lantern, has lost its original Romanesque forms and has a Baroque interior dating from the end of the 17th century. The gabled façade, though altered by the restoration of the first half of the 20th century, has a lower part in stone and an upper part in brick, with a central rose window. On the sides of the latter are still visible the coats of arms of the Cavalieri di Santo Stefano (Knights of St Stephen), to whom the church was granted by the Grand Duke of Tuscany after the abandonment of the Vallombrosians in the second half of the 16th century. It then passed to the Carmelites and became a parish church in 1816.

The second Vallombrosian monastery in the city was the one dedicated to Saints Philip and James, known as Abbadia Nuova (New Abbey), built during the 13th century and, like Abbadia Vecchia, abandoned three centuries later. Occupied by the nuns of St Clare and later by Olivetan monks, it was suppressed in 1866 and later adapted to accommodate a military barracks. Apart from the cloister, very little remains of the old monastery: the church presumably had a brick façade on a stone base, with a large central oculus and a rectangular interior with three naves and five altars. Unfortunately, it was almost completely demolished during World War II when fleeing German soldiers blew it up.


Another form of Benedictine monasticism present in Siena was the Camaldolese. The Congregation was founded by Saint Romuald, a monk from Ravenna who lived between the 10th and 11th centuries. He abandoned the monastery he belonged to in order to satisfy his calling to solitude and his desire to revive the hermitic life. He first lived in Venetian territory and then in Catalonia; on his return to Italy, he received the land of Camaldoli around 1012, where he built a hermitage and a monastery, both independent of each other.

credit Sailko

With his reform, in fact, he did not create any link between monasteries and hermitages, rejecting the Benedictine precept according to which someone who wished to become a hermit had to first serve as a cenobite. The hermits therefore lived in isolation, in separate cells within the hermit’s enclosure, devoted to prayer and the singing of psalms, while the cenobites and monks resided in communal buildings, intent on works of spiritual ministry. The very symbol of the Camaldolese, two doves drinking from a chalice, translates this concept into an image indicating the contemplative life of the hermits and the active life of the monks who quench their thirst at the same source, Christ.

The Camaldolese presence within Siena’s city walls is demonstrated by the former convent complex of Santa Mustiola, or della Rosa, not far from Porta Tufi, which today houses the Accademia dei Fisiocritici (Academy of Physiocritics). Built at the end of the 12th century, the original Romanesque structure has been completely lost due to the changes carried out over the centuries; what remains are the large 16th-century cloister, the neoclassical assembly hall, and the church, now used as an auditorium and conference hall. Its oldest structures are still visible in the transept and in the elegant bell gable with three arches, while the interior is Baroque, with large altars, stucco work, and 18th-century frescoes.

The other seat of the Camaldolese in the city was the centrally located Church of San Vigilio. Erected in the 11th century by the ancient Ugurgieri family of Siena, it was donated in 1131 to the monks who resided in the adjacent monastery, now the home of the University of Siena, until 1420. Passed to the Jesuits and then to the Vallombrosians, the church became a university chapel in 1991 at the behest of the then archbishop Gaetano Bonicelli, with the intention of ensuring adequate pastoral care for students. The building has a brick façade finished with a tympanum enclosed by a notched pediment. The interior, consisting of a rectangular hall flanked by side chapels, features rich sculptural ornamentation and a majestic wooden coffered ceiling with paintings by Raffaello Vanni depicting the Giudizio Universale (Last Judgement).

I Comuni di Terre di Siena