San Casciano in Val di Pesa
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The village of San Casciano a Decimo, already flourishing by 1187, most probably originated as a stage-post on the road to Rome, near the Parish Church of Decimo. Part of the Bishopric of Florence, San Casciano later became an important outpost in the war against Siena. When Florence Commune regained control over the region during the 13th century, it stationed its officers here, removing authority from the bishops and the local feudal lords. San Casciano suffered constant attacks from Florence’s enemies because of its strategic position: one of the most severe attacks was at the hands of Emperor Henry Vll, whose troops pillaged the entire area in 1312. Worse still, in 1326, the army of Castruccio Castracani, Lord of Lucca, burnt the town to the ground. In 1355 the Florentine Republic spent 35.000 gold florins to rebuild its walls, and works were concluded in little more than a year. Under the Medici, the fortifications and the walls were strengthened and enlarged in view of the war against Siena. In the 17th century part of the walls, having lost their defensive function, were dismantled, but a stretch remains along with an imposing tower, on piazza della Repubblica. In 1997 “The Deer” by Mario Mew was placed on the wall: an aluminum deer followed by neon numbers reproducing the Fibonacci series, a statement of the famous Arte Povera exponent’s interest in the universal order generated by this mathematical progression. The fortified tower rises above the town houses, today nos. 8-17 piazza Cavour, and was originally the seat of the lord of the castle and of the garrison. The Medici used this building to accommodate their noble guests who stopped in San Casciano. In the 17th century, Grand Duke Ferdinand II donated the palace to his secretary, Giovanni Paolsanti Lucardesi, who subsequently restored it.
La Collegiata
Not far from the garrison tower is the 12th century church dedicated to Sun Cassiano. By 1487 the church had gained so much importance that it was promoted to Provostry by request of the rector Santi di Tommaso, then becoming Colleggiata, a collegiate church, in 1641, thanks to the legacy left by Antonio Lucardesi. In 1753 the Florentine architect Lorenzo Pozzolini, reconstructed the church in neo-Classical style, with a simple plastered facade broken by pietra serena architectural features. Inside the church, the same linear taste of that period prevails: the stucco moldings, partly tinted in recent restorations, outline the sequences of the three naves. Near the entrance, on the right wall, is a 14th century fresco from the old church depicting the Madonna del Latte, Saint John the Baptist, Saint Stephen and a patron. A small Baroque cabinet on the second altar preserves the relics of Saint Cassiano, a 3rd century martyr. In the main chapel is a wooden Crucifix attributed to Baccio da Montelupo, a sculptor friend of Michelangelo, active between the late 15th and early 16th centuries. In 1797 the painter Luigi Pistocchi from Faenza was called in to fresco the apse with the Glory of Sun Cassiano. On the left, the altar that Francesco Giovanni Paolsanti Lucardesi had erected in the old church in 1612 has been reconstructed. It displays a fragment of a fresco by a 15th century artist close to Filippo Lippi, detached from the wall of a house in Borgo Sarchiani. The canvas which originally belonged to this altar has been moved to the next altar. It depicts the Triumph of the True Cross and was commissioned by Lucardesi to the artist Giovanni Montini. In the painting Lucardesi, secretary to three Grand Dukes, is portrayed with his wife and his mother, while the faces of Emperor Constantine and Saint Helen are in fact portraits of Cosimo II and his mother, Cristina of Lorraine. On the first altar on the right is a panel depicting the Annunciation, originally kept in the Oratorio Dell’Annunziata, which once stood next to the old church. This interesting early 16th century painting has been attributed to the friar Fra Paolino Pistoia. In the background, through the arcades of the portico, the artist has painted a view of Florence as seen from the hills of Sen Casciano.
Santa Maria in Prato
At the heart of the historical town is piazza Pierozzi, dominated by a Baroque clock tower. Two important roads meet here: the Medieval Roman road and the via Empolese. Many small 16th century palazzos line the road that once led out of town through Porta Romana, now via Machiavelli. From the square, the road leading to Porta al Prato is named after the famous tragic actor Antonio Morrocchesi. The San Casciano born actor, greatly admired by the dramatist Vittorio Alfieri, lived at the beginning of the 19th century. On this road stands the Church of Santa Maria in Prato, built in 1304 by the Dominican friars of Santa Maria Novella in Florence. The exterior has kept a simple Gothic appearance, while the interior of the church was embellished in the 17th century by four Baroque side altars: two of these, commissioned by the Bambagini in 1624, display paintings by Jacopo Vignali, a Circumcision and a Madonna of the Rosary. On the right wall are two masterpieces: a painted Cross attributed to Simone Martini, the foremost 14th century Sienese artist, and a green and white marble pulpit by Giovanni Balduccio, a Pisan sculptor active in the Florentine area around the 1340s. The Baroque structure of the High Altar frames Madonna and Child by Ugolino di Nerio, an early 14th century Sienese painter, greatly influenced by Duccio di Buoninsegna, whose fluent Gothic forms are rivalled in this work. The panel once formed a polyptych with the panels of Saint Lawrence and Saint Thomas, also by Ugolino, which now hang on either side of the altar. The Madonna and Child is now flanked by the images of Saint Peter and Saint Francis by the late 16th century artist Rutilio Manetti. The second altar on the left was erected by Camillo Borromeo, of the Milanese family, who owned the villa just outside San Casciano. Its altarpiece representing Saint Carlo Borromeo, painted by Francesco Furini in 1624, bears witness to the local cult of the Milanese saint. At the far end of the left wall, in a frame from the same period, is a panel by the Dominican friar Paolino da Pistoia: a Madonna and Child with Saints John the Baptist and Peter Martyr and the Mystical Marriage of Saint Catherine, dating to 1516.
Museo d’Arte Sacra
Santa Maria del Gesù is further along via Roma: originally a church and monastery of the Franciscan Friars of Primitive Observance,the buildings became a convent in 1492. During the 17th century Francesco Giovanni Paolsanti Lucardesi built, at his own expense, a new complex for the Benedictine nuns, who educated young ladies. Since 1825 the church has been officiated by the Compagnia del Suffragio, a confraternity established during the plague of 1630. The facade was rebuilt after the Second World War. The inside walls are decorated with 17th century pietra serena altars. On the far left, under the organ’s choir, lies the body of Lucardesi. On the right wall is a panel, from the Pieve Vecchia in Sugana, which depicts Saint Sebastian between Saints Anthony and Rocco, one of the few surviving works by the artist, thought to be northern European, known as the Maestro di Tavarnelle. The panel is evidence of the artist’s presence in Chianti in the early 16th century, its background showing a view of Cerbaia, seen from the hill of the parish church. A sculpted pillar made of calcareous alabaster, from the Pieve Vecchia, was perhaps once the base of a baptismal stoup. The scenes of Christ’s Nativity sculpted in a Romanesque style with strong Classical accents are probably the work of the Maestro di Cabestany, active in Roussillon, but present in Tuscany during the second half of the 12th century. The altarpiece depicting the deeds of Saint Michael Archangel, originally housed in the church of Vico L’Abate, is a veritable masterpiece of Romanesque painting. It is the work of Coppo di Marcovaldo, a Tuscan painter who, before even Cimabue, attempted to break away from the Oriental stylizations of Byzantine art. His search for a dramatic effect is not as evident in the frontal hieratic figure of Saint Michael as in the lateral scenes. The Madonna and Child by Ambrogio Lorenzetti, dated 1319, is another work of great historical importance. Despite the intentional archaism of theVirgin’s rigid frontality, the influence of Giotto’s new theories can be seen in the plasticity of the figure and in the hint of perspective in the representation of the throne. The upper floor houses a rich collection of holy relics,splendid church furnishings and paravnents dating between the 16th and 18th Centuries.
Santa Chiara e San Francesco
The Church and Convent of Santa Chiara and San Francesco lie at the end of viale San Francesco d’Assisi, in an area outside the town walls. The complex was built in 1492 by the wealthy Sancascianese Girolamo Castrucci for the Franciscans who had left the Monastery of Santa Maria del Gesù. The front portico was added to the church’s facade in 1736.The simple interior consists of one nave, and a chapel on either side of the entrance. On the right altar is a 16th century wooden Crucifix, a fine sculptural work dating to the 1370s. The presbytery has preserved its late 15th century architectural characteristics but is reserved for the nuns of the Clarissan enclosed order who still live in the convent. A polychrome terracotta statue Saint Clare by the contemporary artist Luigi Mattel, famous for his Holy Doors of the Church of Santa Maria Maggiore in Rome, stands on the altar. In the left chapel there is a beautiful panel depicting a Madonna and Child with Saint Francis and Mary Magdalene, attributed to the painter Biagio d’Antonio da Faenza, who worked in the second half of the 15th century.
Banca del Chianti
The Banca del Chianti is on the left-hand side of the road which leaves San Casciano in the direction of Florence. Designed by Roberto Magris and Cristiano Toraldo di Lancia, the 1990s monumental complex has two aspects:one looking out towards the town, with the piazza delle Arti e Mestieri, the rounded tower containing the bank’s offices and the entrance portico; the second, facing open countryside, is characterized by alternating brick and calcareous stone bands. A bronze sculpture by Roberto Barni, “the Cockrel’s Yarn” dated 1999, rises in the piazza. The artist has placed animals, work tools, and natural elements one on top of the other, modeling them in such a t way as to celebrate the sensory quality of the material. On top of this complex structure of symbols alluding to man, Christianity and mythology, is a cockerel, the symbol of Chianti, whose crow marks the beginning of day for humanity.
Leaving San Casciano in the direction of Florence, on the right-hand side of via Cassia is the small Oratory of San Bartolomeo. This small church and the annexed pilgrim’s hospital once stood at the entrance to San Casciano, leaning against the town walls. Together with Villa La Palagina, it belonged to the Ridolfi, enemies of the Medici: in 1579 all their property was confiscated and their lands in San Casciano went to the Certosa, the Charterhouse of Florence, whose emblem decorates the oratory’s facade. A little further on, a right turn leads to the Parish Church of Santa Cecilia a Decimo. At the roundabout a left turn is via degli Scopeti, which leads to Sant’Andrea in Percussina.
The Map of The Area:

The Map of The Area Around San Casciano
- Cappella dei Pesci and San Giovanni Gualberto
- Badia a Passignano
- Chiesanuova
- Il Morrocco
- La Romita and Poggio Petroio
- Luiano
- Massanera
- Montecchio
- Mulino dell’Abate and Santa Maria a Cerbaia
- Museo Arte Sacra (Sacred Art Museum)
- Pietracupa
- Pieve di San Donato in Poggio
- Poggio a Vento
- Sambuca Val di Pesa
- San Donato in Poggio
- San Giovanni in Sugana, Villa Talente, Mucciana
- San Martino ad Argiano and Villa Antinori
- San Pietro in Bossolo
- San Polo di Torre
- Sant’Andrea in Percussina
- Santa Cecilia a Decimo
- Santa Lucia al Borghetto
- Spicciano and Casaglia
- Tavarnelle Val di Pesa
- Tignano and Prumiano
- Torre del Chito and Cortine
- Via Volterrana to Cerbaia
- Vico l’Abate, Castello di Gabbiano, and Novoli
- Villa Mangiacane
- Villa Poggio Torselli
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