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The Valdichiana. what to see
This valley was originally a lake which dried out during the time of the Etruscans and the Romans. Over the centuries, it has been subjected to a series of complex and laborious drainage works. Despite this, however, the presence of mountain ridges and hills situated in places of strategic importance along communication routes has meant that, ever since the Middle Ages, populated centres developed along the valley and became veritable treasure houses of art.


Leaving behind the city of Arezzo, and travelling along the eastern side of the valley, you come to CIVITELLA IN VALDICHIANA, a village which had once been a Lombard stronghold before it eventually became a feudal domain of the Bishops of Arezzo after the year 1000. Its moment of greatest development was in the second decade of the 14th century after which, in 1345, it became part of the domain of the Florentine Republic. Linking the present day with the past is the Porta Senese, the ruins of the 13th-century Castle and the Palazzo del Podestà which shows some 15th-century reconstruction work.
Inside the walls, there is also the Chiesa di Santa Maria which, although it dates from the 11th century, has been reconstructed many times. Inside, the Crucifixion and Saints was painted in 1602 by the Arezzo artist Teofilo Torri, pupil of Giorgio Vasari. On the outskirts of the village, there is the Oratorio della Madonna di Mercatale, a simple but picturesque building, constructed by the citizens of Civitella around 1630 in gratitude to the Blessed Virgin for escaping the plague.
The road now takes you to Gargonza. In the early 13th century, this village was a possession of the Ubertini family and, in 1302, during their dominion, tradition relates that there was a gathering here of Ghilbellines and a number of Guelphic bandits from Florence, in which Dante also took part. In 1381, the Ubertini sold Gargonza to Siena from which it was ceded to the Florentine Republic in 1384. Acquired by the Loteringhi della Stufa family in 1546, the village was then sold, in the 18th century, to the Marquises Corsi from whom it passed through inheritance to the Guicciardini family who are still today the proprietors. Of its fortifications, Gargonza retains the tower and the remains of the ancient walls with their 13th-century gate. The Chiesa dei Santi Tiburzio e Susanna is also a medieval foundation, dating from the 12th century. On its portal there is terracotta Madonna and Child with Angels from the Rossellini circle and, inside, a fresco with the Madonna between St Anthony Abbot and St Bernard, dated 1483.
Going back now along the strada statale, you will come to the Santuario della Madonna delle Vertighe who is the patron saint of the Autostrada del Sole. The origin of the shrine lies in a Marian miracle when a small chapel was carried from Asciano by angels in flight and gently set down here, towards the year 1100. In the 16th century, the sanctuary was built around what had become a shrine, and it was restored in 1943. The façade is simple, with two downward inclinations and a portico on hexagonal pillars. The bell tower is a medieval tower topped with a Renaissance crown ascribed to Andrea Sansovino. Inside, the columns which separate the nave from the two aisles are surmounted by Ionic capitals, and the church possesses valuable works of art. In the left-hand aisle, you can see the Nativity of the Blessed Virgin, signed and dated 1627 by the Arezzo painter Bernardino Santini, and the diptych portraying St Savinus and St Romuald is by Ridolfo del Ghirlandaio, from 1520. In the apse there is a very precious wooden triptych which depicts the Madonna delle Vertighe and four Marian Stories in the central panel and, in the side panels, Three Male Saints and Three Female Saints. The work is by Margarito and Ristoro d’Arezzo, and is signed and dated 1274 or 1283. The small Romanesque apse which dates back to the 11th and 12th centuries is the building which, according to tradition, was miraculously brought from Asciano to the Vertighe hill.
The Crucifix in the nave on a profiled panel was painted by Lorenzo Monaco between 1415 and 1429. In the left-hand aisle, the fresco of the Assumption of the Blessed Virgin was painted in 1590 by Orazio Porta.
CORTONA was founded by the Etruscans and, after the Roman Empire, in the year 450 it was conquered by the Goths. Subsequently, in the 12th and 13th centuries, it became a free commune but was sacked by the forces of Arezzo in the mid-13th century, and almost the entire population was forced into exile. The inhabitants were not allowed back until 1261. After continuing vicissitudes, Cortona became a dominion of Florence in 1411, and from the time of Pope Clement VII the town’s fortunes were those of the Duchy and of the Medici family. You should first make your way to the Palazzo Comunale which was built and rebuilt in the course of the 13th century, but which was heavily restored in the 19th century.

In the adjacent Piazza Signorelli, you will find Palazzo del Capitano del Popolo which once housed the town administrator. It was built during the 13th century but transformed in the course of the 16th century to become the residence of Cardinal Silvio Passerini. Looking on to the same piazza is the Palazzo Casali built by the Casali family during the 13th century. It became an official residence when, between 1325 and 1409, the offspring of this family commanded the regiment of Cortona but, after 1411 when the town passed into Florentine hands, the building became the residence of the “capitani” sent from Florence. During the 18th century, it became the seat of the Accademia Etrusca, an important institution which conserves historical Archives, possesses a richly endowed Library, and houses a Museum. The nucleus of the collection in the Museo dell’Accademia Etrusca was a donation made in 1727 by the Abbot Onofrio Baldelli, from Cortona. Other bequests and donations were subsequently added. There is a collection of Etruscan, Roman and Egyptian art, including an enormously significant Etruscan lamp holder from the 4th century BC and an Egyptian wooden funeral barge. There is also an art collection ranging from the 13th to the 19th centuries, including works by Luca Signorelli, Matteo Lappoli, Cristofano Allori and one of the most important exponents of 17th-century painting, Pietro Berettini, more commonly known as Pietro da Cortona who was born here in 1596.
From Piazza Signorelli, you can walk to the Duomo which Giuliano da Sangallo, or more probably one of his imitators, built on the remains of a Romanesque pieve, of which some traces remain on the façade. The interior with its nave and two aisles was remade during the 17th century. You can see a Crucifixion and Doubting Thomas by the school of Luca Signorelli. This artist was born in Cortona around 1445 and, although he learnt his art in Florence, he remained deeply attached to his birthplace and created many works of art for the town. Also in the Cathedral there are works by Papacello, Andrea Commodi and Francesco Morandini who was known as “il Poppi”. The nearby ex-Chiesa del Gesù, built between 1498 and 1505, houses the Museo Diocesano del Capitolo in which you will find a good many art-works, especially the Annunciation by Frà Angelico and a Crucifix by Pietro Lorenzetti from 1315-1320, both masterpieces in their own right. Frà Angelico also did a Madonna and Child and four Saints from 1435 with Episodes in the Life of St Dominic in the predella, while Lorenzetti painted a Madonna and Child and Angels. Among the other works, there are some by Luca Signorelli, including Lament for the Dead Christ from 1502 and the Community of the Apostles from 1512. The Assumption, which dates from the 1570s, is ascribed to Bartolomeo della Gatta, who was a friend of Signorelli. There are also many examples of the goldsmith’s art and numerous sacred objects in the Museum’ possession.
Works by such Florentine artists as Alessandro Alllori and Jacopo Chimenti known as L’Empoli, of the late 16th and early 17th centuries, are conserved in the late-Renaissance Chiesa di San Maria Nuova. The Gothic Chiesa di San Francesco, was begun in 1245 by Friar Elia, the founder of the Basilica of Assisi, but was remade between the 16th and 17th centuries. The church possesses notable art works, frescoes and canvasses of the schools of both Florence and Siena. On the high altar of the 15th-century Chiesa di San Nicolò there is the “gonfalone”, or banner, of the Society of San Nicolò, made by Luca Signorelli, depicting Christ Deposed from the Cross with Saints and Angels on one side and, on the other, the Madonna with St Peter and St Paul. From the circle of the same artist, and close to the church’s entrance, there is a fresco of the Madonna and Child with Saints. From this part of the town, you go up to the Sanctuary dedicated to Santa Margherita da Cortona. Situated on a hilltop from which you can enjoy a wonderful view of the valley below, the Sanctuary was built in 1859. Inside, in addition to art-works of interest, there is the tomb of Santa Margherita made in a Gothic style in 1362.
Your visit to Cortona finishes with a visit to the Fortezza Medicea, also known as the Fortezza del Girifalco, which Cosimo I de’ Medici ordered to be constructed in 1556, and the Chiesa di San Domenico dating from the early 15th century. Adjacent to the church there used to be a monastery, now destroyed, in which Frà Angelico was a guest when he painted the Annunciation, now in the Diocesan Museum. The artist was a Dominican friar and he also painted the fresco in the lunette of the entrance portal depicting the Madonna and Child between two Dominicans. Inside the church, you will find a detached fresco depicting St Roch and Episodes from his Life by Bartolomeo della Gatta, a Madonna and Child with Saints by Luca Signorelli from 1515 and, at the high altar, a large polyptych by Lorenzo di Niccolò Gerini, signed and dated 1402.
From Cortona, you can also visit the nearby Chiesa della Madonna del Calcinaio built to a centralised plan in 1485-1513 and designed by Francesco di Giorgio Martini. Inside, you find some stained- glass windows made by Guillaume de Marcillat and by his pupils, as well as paintings by Papacello and by the school of Luca Signorelli.

If you leave Arezzo and take the eastern side of the Valdichiana, you pass through Olmo, Puliciano and Rigutino before reaching CASTIGLION FIORENTINO. The origins of this town go back to the late Archaic and Hellenistic age, and are closely linked with its strategic importance in a hilltop position that surveys the vital communication route between Arezzo and southern Italy. There was a link between Arezzo and Castiglione as far back as the year 1000, and both the perimeter of walls which were enlarged in the 13th century and the transformation of the Cassero were due to Arezzo. Later on, it was dominated by Perugia and became known as Castiglione Aretino but, when it became part of the Florentine Republic after 1384, it took on the name it retains to this day. The centre of the town is Piazza del Municipio with the so-called 16th-century Logge del Vasari, opening so wonderfully on to the valley below. Opposite is the 16th-century Palazzo Comunale which was erected above a pre-existing building and which was itself remade during the first half of the 20th century.
The Cassero, or keep, was constructed between the 11th and 12th centuries, and later reinforced during the rule of Perugia with the construction of the Casseretto. Within the building is the Pinacoteca Comunale, or picture gallery, containing art works of great importance. You will see a late 13th-century wooden Crucifix, a San Francesco by Magarito d’Arezzo, a fragment of a Maestà, or Blessed Virgin Enthroned, by Taddeo Gaddi, and two works by one of the leading lights of Renaissance painting, Bartolomeo della Gatta, St Francis receiving the Stigmata made in 1486 and St Michael Archangel which, it seems, the artist painted with one of his pupils, Matteo Lappoli. The gallery also houses medieval masterpieces of the goldsmith’s art, such as the Reliquary Bust of St Ursula from the late 14th century, as well as other pictorial works by Giovanni di Paolo, Jacopo del Sallaio, Papacello and Giovan Domenico Ferretti.
From the Piazza del Municipio, you go down to the lower section of the town where you find three important churches, the Collegiata di San Giuliano, the Pieve Vecchia and the Chiesa del Gesù. The Collegiate Church, which was reconstructed between 1840 and 1853, has some valuable works, including a Madonna and Child Enthroned between Angels and Saints by Segna di Bonaventura, an Adoration by Lorenzo di Credi, and an admirable painting by Bartolomeo della Gatta of the Madonna and Child Enthroned with Saints from 1486. One of this artist’s assistants, Angelo di Lorentino, painted the Madonna and Child Enthroned between two Saints in the second decade of the 16th century. He was the son of the better-known Lorentino d’Andrea, a disciple of Piero della Francesca. The Pieve Vecchia, rebuilt in 1451, is important because it possesses a splendid fresco of the Deposition of Christ painted in 1483 by Luca Signorelli.
Before arriving at Cortona, the jewel of the Valdichiana, you come to the CASTELLO DI MONTECCHIO VESPONI which was a possession of the Guasconi family in the year 1000 but which, after the battle of Campaldino in 1289, came under the sway of Florence. It was awarded to the English soldier of fortune, John Hawkwood, known in Italy as Giovanni Acuto, and still retains a number of 13th-century elements.
The road now takes you to one of the most important farming centres in the valley, FOIANO DELLA CHIANA which was first settled in Etrusco-Roman times. Situated on high ground rising out of the plain, the township was a feudal domain of the bishops of Arezzo in the mid-13th century, and they strengthened it with a double perimeter of walls. Inside the walls, in Piazza Cavour, you find the Palazzo Comunale, a 14th-century foundation but reconstructed in the mid 16th century, and the Palazzo Granducale, which today houses the Municipal Library. This building was constructed by the Grand Duke Ferdinand II de’ Medici who would stay here whenever he was taking part in hunting trips in the district. Among the churches worth visiting is the Collegiata dei Santi Martino e Leonardo built between the 16th and 18th centuries. The brick façade encloses a single nave and six chapels. You can see the Coronation of the Blessed Virgin with Angels and Saints, painted in 1523 by Luca Signorelli who was helped by artists from his workshop, a Crucifixion with the Blessed Virgin and Saints by Orazio Porta and a Blessed Virgin with the Girdle and Saints, a glazed terracotta from 1502 ascribed to Andrea della Robbia.
Next is the Chiesa di San Michele Arcangelo which, with the adjacent Dominican monastery, was built between the first and second circle of walls, at the end of the 14th century. The present façade is the result of a late Baroque remake. The interior has a single nave and three apses, and you will find a glazed terracotta altar piece depicting the Ascension of Christ, probably made at the end of the 15th century by Giovanni della Robbia, and Our Lady of the Rosary between Saints signed and dated 1652 by the painter Lorenzo Lippi. The Chiesa di Santa Maria della Fraternita has a certain interest for the visitor, as does the Chiesa di San Francesco which was completed in the early 16th century, but reconstructed and enlarged between 1756 and 1759. Here you can find an altar piece made by the workshop of Andrea della Robbia which shows Christ and the Blessed Virgin interceding with the Eternal Father and, by the same circle, a Blessed Virgin in the act of Swooning.
Along the road which goes from Foiano to Marciano della Chiana, in the locality of Pozzo, stands the Tempietto di Santo Stefano della Vittoria. Made in 1572 and perhaps to a design by Giorgio Vasari, the building celebrates the annexation of Siena to the domain of Cosimo I de’ Medici which followed after the Battle of Scannagallo in 1554. To show how important these places were, first to the Florentine Republic, and then to the Grand Duchy of the Medici family, the arx of MARCIANO DELLA CHIANA became a fortified citadel in Sienese style with perimeter walls, some sections of which still remain. Inside the walls, you will see the Chiesa dei Santi Andrea e Stefano with some art works of a certain importance, including the Madonna and Child Enthroned between St James and St Christopher by Bartolomeo della Gatta from 1493.

From Monte San Savino, it is easy to reach another small township abounding in artistic works, LUCIGNANO. Situated on the edge of a hill in lands that were already inhabited in Etruscan times, the town grew out of a Roman “castrum” or military camp, strategically located in this important position on the road between Arezzo and Siena. For this very reason, the site was the subject of conflicts between the two cities and, later on, between Perugia and Florence. Present-day Lucignano has retained unchanged the elliptical plan and street layout which it was given between the 12th and 14th centuries. The ellipse developed around the oval shape of the early medieval nucleus of buildings. Entering through Porta San Giusto, you come to Piazza Caduti della Libertà, and the 14th-century Cassero, or castle keep, rises above the piazza. It possesses a square tower with a portico built in the 18th century to the design of Andrea Pozzo. The same artist designed the stage-set of steps that go up to the Collegiata di San Michele Arcangelo which was built in 1594 on the site of an older church by the artist from Monte San Savino, Orazio Porta. Inside the single nave, you will find two statues by Andrea Pozzo, St Peter and St Paul. Matteo Rosselli the Florentine artist painted the Visitation of the Blessed Virgin to St Elizabeth in 1631, and another Florentine, Onorio Marinari, painted the Death of St Joseph in 1668-1670. St Charles visiting those stricken with the Plague and the Martyrdom of St Lucy were done by Giacinto Gimignani who learnt his art in Cortona. In the Chapel of the Blessed Sacrament, built between 1668 and 1672, there are frescoes painted by Luigi Ademollo between 1792 and 1798. Behind the Collegiate Church, you will find the 14th-century Palazzo Comunale which looks on to the Piazza del Tribunale and inside which the Museo Comunale has been housed since1984. In the Museum’s collection, there is a 14th-century Madonna and Child Enthroned with Saints by the Sienese artist, Lippo Vanni, St Francis receiving the Stigmata by Luca Signorelli, a Madonna and Child Enthroned with a Female Donor by Niccolò di Segna, and a triptych by Bartolo di Fredi.
However, the most singular and most precious item in the Museum is the reliquary known as the Albero di Lucignano, called so because it has the shape of a tree. The Albero is made of gold-plated copper and silver, and the branches are of coral and rock crystal and hold miniature images. This complex work, which was started in 1350 but not finished until 1471, was assigned to master craftsmen from Siena and Arezzo and also to Gabriele d’Antonio.
From the right of the Palazzo Comunale, you go down to the Chiesa di San Francesco which was built during the 13th century and retains its Romanesque grey and white façade with a Gothic portal. The floor plan is a Coptic cross with a single nave. The church possesses the remains of some frescoes ascribed to Bartolo di Fredi, Taddeo di Bartolo and other artists from Siena who were working between the 14th and 15th centuries, and among these is the Triumph of Death. The polyptych at the high altar, the Madonna and Child with Saints, is ascribed to Luca di Tommè and was painted during the second half of the 14th century. From the right of San Francesco, you reach the Oratorio di Santa Maria della Misericordia, or Our Lady of Mercy, which was founded before 1468 and reconstructed before 1583. Inside, there is a single nave and a Nativity at the main altar which is perhaps by Orazio Porta. At the side altars, there are two works from 1699, an Annunciation by Onorio Marinari from 1699 and an Assumption of the Blessed Virgin by Alessandro Gherardini. Outside Porta San Giusto but near Lucignano, you find the Santuario di Santa Maria della Querce which grew up around an image of the Blessed Virgin painted in 1417 by Feliciano Batone. In 1467 a miracle related to this image took place and a chapel was built. It was substituted in 1564 by the building you see today ascribed to Giorgio Vasari. Inside, there is a painting from 1625 by the Florentine artist Matteo Rosselli.

As you leave the Marian Sanctuary behind, the road leads to MONTE SAN SAVINO. The small township sits on a hilltop and has Etruscan origins. It was later dominated by the Romans, then the Goths, and was for a long time contested between Ghibelline Arezzo and Guelphic Florence, with dominion passing backwards and forwards from one city to the other. Destroyed in 1325 by the militia of the Bishop of Arezzo Guido Tarlati, it became for a time the possession of Perugia until, in 1384, it was definitively annexed by the Florentine Republic. During the 15th century, Monte San Savino enjoyed comparative tranquillity and this enabled the Ciocchi family to rise socially. Orginating in Florence, the family had in Fabiano Ciocchi, later known as Ciocchi di Monte, their first truly influential representative at the Roman Curia. It was, however, in the 16th century when Fabiano’s son, Antonio, became Cardinal that the fortunes of the Ciocchi family reached their greatest heights. As the
pre-eminent expert on canon law in the Roman Curia, Antonio became endeared to Pope Julius II and to the Medici Popes, and it was this position that opened the way for the election to the papacy of his nephew, Giovanni Maria di Monte. He took the name Julius III and reigned from 1550 to 1555. Subsequent to this event, the Duke of Tuscany, Cosimo I de’ Medici, conceded Monte San Savino to Balduino del Monte, the Pope’s brother, making it a county. However, when the family line finished in 1569, the township returned to Florentine domain. From 1604 to 1640, it was subordinated to the Orsini Marquises and then became the personal domain of Mattias de’ Medici, brother of the Grand Duke Ferdinand II, and subsequently the domain of the Grand Duke’s wife, the Grand Duchess Vittoria della Rovere, only to return to the Grand Duchy’s domain in 1748.
The 13th-century perimeter of walls, which were reconstructed in the 14th century and restored in later centuries, still surround the town and give access through their four gateways. The Porta Fiorentina was made towards the mid-16th century by the architect Nanni di Baccio Bigio. It has a powerful tower with a lunette, into which the impressive coat-of-arms of the Medici family were placed in 1572. From this gateway, you arrive at Piazza Gamurrini in whose centre stands the guglia, a small obelisk, which was made in 1644 and commemorates the year when Prince Mattias de’ Medici received his investiture as feudal lord of Monte San Savino.
Built into the wall is the Cassero, or stronghold, a 14th-century rectangular building on a square base with a powerful donjon and four watch towers at the corners. Its construction has traditionally been ascribed to the architect Bartolo di Bartolo. Restored in the 1970s, the building is now the Museo Comunale where a rich collection of ceramics is on display, ranging from the Middle Ages to the present time. There are also some works coming from other buildings in the town, among which is a Crucifix of the school of Siena from the first quarter of the 14th century. Near the Cassero is the ex-Chiesa di Santa Chiara and next to it is the ex-monastery. The church was built between 1659 and 1661 and possesses some important art works, among which are two altar pieces, the Pala of St Lawrence and the Pala with the Blessed Virgin and Saints, made by the sculptor and architect, Andrea di Menco di Muccio, better known as Andrea Sansovino because this township was his birthplace. He made these pieces in the late 15th century when he was mixing in Lorenzo the Magnificent’s favoured art circles in Florence, the city where he learnt his art. In the same building, there are two paintings by either Guidoccio Cozzarelli or Matteo di Giovanni, St Roch and St Ansanus and St Apollonia and St Sigismund, which can be dated to about 1465; a glazed polychrome terracotta from the workshop of Andrea della Robbia which depicts a Nativity Crib; an Annunciation from around 1570 by the painter and architect Orazio Porta who was born in Monte San Savino in 1540 and who learnt his craft in Vasari’s circle.
If you walk along Corso Sangallo, close to the piazza you will find the Palazzo di Monte on the right. Cardinal Antonio di Monte was responsible for this building and commissioned the design from the architect Antonio Sangallo the Elder in the second half of the 16th century. Sangallo designed the façade and the plan of the palazzo, while the courtyard and the rear of the building, as well as the hanging garden, were later completed by Nanni di Baccio Bigio. Today, the palazzo is the City Hall and presents an imposing façade. The rusticated lower section is contrasted with the grey sandstone upper section . The simple but attractive courtyard leads out into the hanging garden located above a large water cistern, and from here you have a good view of the rear of the palazzo. Inside is the Quadreria Comunale, or Municipal Picture Gallery with portraits of Monte San Savino’s most illustrious personalities, as well as of some of Tuscany’s ruling families. The oldest example of these paintings was done in 1650 by the local painter Francesco Giovannoni.
In front of this once manorial residence you see the Logge, which seem to be a natural finish to the Palazzo. These loggias were long attributed to either Antonio Sangallo or Andrea Sansovino, but their construction is now given as after 1547 and perhaps it was the work of Nanni di Baccio Bigio, if not of Niccolò Soggi, painter and architect who was born in Monte San Savino in 1479 but trained in Florence.
On the same side of Corso Sangallo stands the 14th-century Palazzo Pretorio with the civic tower in its centre. The construction of this building is attributed to the time when Monte San Savino was dominated by Perugia. On the other side of the street, you can see the Pieve dedicated to St Egidius and St Savinus. Although built in the 12th century, the orginal Romanesque form has been greatly changed over the years. It was reconstructed during the 15th century by the architect Sandro Bambocci, remodernised in the 17th century and rebuilt again between 1748 and 1749 by the master from Varese, Pietro Materno Speroni. Although the plain façade faces Via della Misericordia, the present-day entrance is from the left-hand side. The interior has a single nave with a trussed wooden ceiling, six lateral altars and two chapels flanking the high altar. On the second altar to the left, the painting of Our Lady of Mount Carmel with Saints was done by Astolfo Petrazzi from Siena; the first altar on the same side has an altar piece with the Blessed Virgin and Saints painted in the second half of the 17th century by the local artist Domenico Sozzini. The Funeral Monument to Fabiano Ciocchi di Monte has been reassembled under the choir stalls. Originally placed near the high altar, it was made after 1498 probably by Andrea Sansovino. Above the choir stalls is a monumental organ whose nucleus dates back to 1506. The first altar on the right has an altar piece by Orazio Porta from the end of the16th century, depicting St Peter and St Paul. The high altar in stucco and false marble is by Pietro Materno Speroni, while in the chapel to its right there are some late 15th-century frescoes, probably by Niccolò Soggi.
Corso Sangallo ends in Piazza Di Monte where you find the Chiesa di Sant’Agostino. It was reconstructed before 1356 on the site of a pre-existing building and then enlarged yet again in the 14th century. During the 16th century, Andrea Sansovino reorganised the piazza in front of the church and then constructed the vestibule which you find inside.
From the 18th to the 20th century, the church has undergone a number of enlargements. From the outside, the façade is shaped into two downward inclinations. There is a richly decorated portal, with a pointed arch supported on spiral columns, and a 15th-century panelled wooden door. The upper section has a stained-glass ox-eye window decorated with St Augustine and Angels, and made in 1524 by the workshop of Guillaume de Marcillat. Inside, with a single nave and trussed ceiling, Andrea Sansovino’s vestibule made around 1525 is constructed against the counter façade. The wooden choir stalls from the end of the 16th century possess a 16th-century organ made by Dionisio Romani. If you start from the counter façade, on the right-hand wall there are two frescoes ascribed to Giovanni d’Agnolo di Balduccio, a disciple of Spinello Aretino, the Presentation in the Temple and the Adoration of the Magi. Under the first painting you can see the date 1408 and the names of those who commissioned the work. Further on, the fresco depicting St Lawrence and Episodes from his Life is from the school of Spinello Aretino from the end of the 14th century. In the second bay, above the choir stalls, the Madonna in Glory with Saints is presumed to be by the Arezzo painter Domenico Pecori from the 1620s. In the presbytery, the Annunciation is from the 16th-17th century and has been ascribed to Ulisse Giocchi, a painter originally from Monte San Savino who had been trained in Florence, and the Adoration of the Magi by Orazio Porta is dated around 1580. At the centre of the high altar, there is an Assumption of the Blessed Virgin with St Augustine and St Romuald, signed and dated by Giorgio Vasari in 1539. The frescoes in the vault above were painted in 1933 by Ovidio Grignoli di Arcidosso. Still in the presbytery, you can see a signed Nativity and the Blessed Virgin in Glory crowning St Lucy and St Catherine of Alexandria, both painted by Orazio Porta in around 1580-1581. Another work by Porta, the Resurrection of Christ, from 1581, is on the left-hand wall of the church. The carved and gold-plated pulpit, from 1642, incorporates two paintings that once functioned as doorways and which depict the Blessed Virgin on hearing the Annunciation and the Angel making the Annunciation, both made by Orazio Porta in around 1570. After this is the Tombstone of Andrea Sansovino, the sculptor who died here in 1529. At the first altar, you see a fresco of the Pietà and Saints made by Paolo Schiavo around 1440 and the Holy Trinity surrounded by Prophets, a fresco from the end of the 14th century by the school of Spinello Aretino. On the counter façade there is a Crucifixion which has been ascribed to Giovanni d’Agnolo di Balduccio, from the beginning of the 15th century.
Although part of the monastery adjacent to the church was utilised for its extensions, its Cloister was preserved. It is on two floors and was made by Andrea Sansovino before 1528. According to what Vasari wrote, there were frescoes here by Antonio di Donnino del Mazziere depicting “Episodes from the Old Testament”, but no other relevant documentation exists.
To the side of the Church of St Augustine, you find the 15th-century Chiesa di San Giovanni which was orignally an Oratory dedicated to St Anthony. The beautiful portal was made by Andrea Sansovino towards 1528. In front of the church is the Casa di Andrea Sansovino, which the sculptor and architect built here above pre-existing buildings belonging to his family.

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