La Lastra Siena Visit of vineyards
and cellar with wine tasting and light-lunch Le Caggiole farmhouse in San Gimignano Bed Breakfast La Fornace di Racciano  San Gimignano - Siena Relais della Rovere hotel relais colle val d'elsa Siena Agriturismo Cesani San Gimignano - Siena

Castiglion Fiorentino

The inhabited nucleus of Castiglion Fiorentino was developed in the Etruscan period and the Hellenistic period. After the Romans conquered the Arezzo territory they organized agricultural production in the form of villas.


Castiglion Fiorentino  - ArezzoHistory
The inhabited nucleus was developed in the Etruscan period (6th - 5th c. BC) and the Hellenistic period (4th c. BC). After the Romans conquered the Arezzo territory they organized agricultural production in the form of villas. During the reign of the Emperor Augustus, the Valdichiana began a period of decline; the population, due to the flooding of the valley, moved to the hillside areas that were safer and more salutary. The construction of the parishes began at this point, connected along a footpath in the hillside and the roadway of the Val di Chio. Documents date the town with the name of Castiglione in the 10th century when it became the feudal property of the Marquis of Monte S. Maria.
In the following centuries, while it remained under the protection of the emperor, the township belonged to the diocese of Arezzo. Following the defeat of Arezzo in Campaldino (1289), the township passed to the domain of Florence. In 1303 it was again conquered by Arezzo and Siena, lead by the mayor Uguccione della Faggiola. Bishop Guido Tarlati, who became monsignor of Arezzo and its territory expanded the city walls and modified the urban structure. With the death of Tarlati, Castiglione Aretino returned briefly to the Florentine domain (1336 -1344). In 1344, it was conquered by Perugia and renamed Castiglione Perugino. In 1369, the population rebelled against Perugia, putting themselves under the protection of the church state. In 1384 the town passed finally to Florence and was renamed Castiglion Fiorentino. The beginning of the 15th century brought a period of crisis due to the epidemic of the plague and the subsequent famine. During the war between Florence and the Republic of Siena, Castiglione fell into the hands of Piero Strozzi, returning briefly under the rule of Florence (1554).
The Medici government was followed by the Lorena (1765) who, reclaiming the Valdichiana, created the proper conditions for strong demographic development, social changes,, and a large economic boost. The Florentine domain ended in 1799 when the Tree of Liberty was raised in the Piazza del Mercato. From 1800 to 1814 the township was garrisoned by Napoleons troops. With the f all of the French government, the Lorena returned in 1814 and began reclaiming the Valdichiana. Castiglion Fiorentino then followed the fate of Tuscany and the Italian Republic. The passing of the war front during World War II caused notable damage to both the historic center and a large part of the surrounding territory.

Castiglion Fiorentino -  the walls - ArezzoThe Walls
The first Medieval city wall went up in the 13th century. It was enlarged in the 14th century and the "Muro dell'Ala" ("Wail of the Wing") was built to connect the Cassero to the outside walls. Around the middle of the 1300's, the Perugians, rulers of the township, brought about further reconstruction. During the 1600's, the towers were partially torn down. The principal access to the historical center is by the Florentine Gate which was part of the wall circuit of the 1200's. It was last remodelled in 1813. On the outside there is an anti-gate to the left of which is a Medici coat of arms; the inside of the gate is made up of three arches above which is a statue of S. Michele, patron saint of the town. To the left, the walls wind towards S. Francesco. The outer part, called Pisan walls for the participation of the Republic of Pisa in their construction, leads to Piazzale Garibaldi. Remains of other two towers can be seen along this wall. Towards the present Gate of S. Giuliano, the walls descend to enclose the ecclesiastical complex of the Collegiata and then continue towards the Roman Gate, that is the 13th century Gate of S. Angelo. Above this last gate is a niche with a terra cotta statue of S. Michele. Ahead, we find the Town Theater built into the city walls.
The area of the Cassero
Castiglion Fiorentino Il CasseroPiazzale del Cassero
The archeological digs conducted here unearthed evidence of an Etruscan city wall (ca. 4th e. BC) made up of large stones and the remains of a city gate. Next to the Palazzo Pretorio (Courthouse), the digs, which are still in progress uncovered evidence of a sacred ground used from the end of the 5th e. BC until the 2nd C. AD.
During the 11th century the first center of Castiglione was formed here. During of the rule of the Tarlati in the first decades of the 14th century, the area was turned into a small fortress, developed along with the construction of the Casseretto in 1367 and the well in 1368. The Perugians reconnected the Casseretto with the external wall circuit by means of the so-called "Muro dell'Ala' ("Wall of the Wing").
Orologio della Torre del Cassero - Castiglion Fiorentino Following this, the area became the property of the Republic of Florence that then sold it to the Castiglionese in 142 l. In the 16th century, the nuns of S.Girolamo used a part of this area to build their convent. In the 19th century some of these structures were transformed into prisons and in 1845 the gate and drawbridge were destroyed.
Palazzo Pretorio (Courthouse)
The palace was built in the 15th century. Objects found during the excavations in the Piazzale are on display in the ground floor rooms. Among these are noted a sima decorated with lilies and rosebuds and a painted terra cotta lion's head. Etruscan and Roman finds discovered around Castiglion Fiorentino are also on display. The public library is also located inside the Court House building.
Pinacoteca (Municipal Art Gallery)
The Municipal Art Gallery, in addition to being a museum space, also includes the Church of S. Angelo.
There is evidence of a chapel dedicated to S. Angelo dating back to the 12th century. The church was built in the R,omanesque style between 1229 and 1239. In 1532, the nuns of S. Girolamo were granted its use.
During this period two important modifications were made : the original orientation of the church was reversed closing off the original portal and moving the entrance to the southern side of the building; the "Coro delle Monache" ("Nuns Choir") was built in place of the apse.
Following the Leopold abolition of the convent (1785), the church underwent many disparate uses: hospital, wine cellar, workshop. The building was recently restored and included as part of the Municipal Art Gallery Works of art on display include a cross of the Umbrian School (13th century), two panels by Jacopo di Sellaio (15th century) and The Virgin with Child and Saints (1549) by Giorgio Vasari. The church leads to the guard room and from here to the hall of S. Orsola that holds valuable works of gold including the Reliquary of S. Orsola from the 14th century. From this hall, a staircase, leads down to the crypt of S. Angelo. The entrance to the Pinacoteca is on the first floor, where several important works are on display in the large hall: Crucifixion (early 13'h e.) from the workshop of Margarito d'Arezzo, a Madonna with Child (ca. 1328) by Taddeo Gaddi, panels by the Siena school, The Stigmata of S. Francesco (1486) and S. Michele (ca. 1480) by Bartolomeo della Gatta, Madonna with Child and S. Giovannino (middle 16th e.) from the workshop of Ridolfo del Ghirlandaio, Madonna with Child and S. Anna (first half of the 16th c.) by Papacello, and the Ecstasy of S. Teresa (1723) by Gian Domenico Ferretti. Some reliquaries and other religious objects are kept in the glass case in the middle of the room. On the top floor is the Tower Room where coats of arms and plaques found in the area of the Cassero are on display.
Vasarian Loggia  - Castiglion Fiorentino - ArezzoVasarian Loggia
The nine arch construction dates back to 1513, during the time of the rebuilding of the main piazza. The traditional attribution to Vasari was verified by the restoration carried out between 1560 and 1570, the period in which the Medici coat of arms was placed there. For structural purposes, three of the arches along the Val di Chio were closed off in 1773, later to be reopened in 1922.
Church of S. Francesco
The construction of this church was begun in 1256 by franciscan monks. The original sandstone facade still stands today. Above the portal is a terra cotta relief of S. Francesco by the Castiglionese artist Antonio Brogi (1946). The stained glass windows were realized in 1419. The simplicity of the interior architectural layout is typical of the Mendicant Orders. Noted works of art include: Virgin in Glory; a fresco on the inside facade wall; the Vocation of S. Matteo (around 1663) by Salvi Castellucci on the first altar to the right; a piece of a fresco of the Virgin with Child; the fourth altar on the right, sculpted by Filippo Berrettini of Cortona with a statue of Christ (1651) by Sallustio Lombardi in the center; Announcement of the Angel to S. Anna in the chapel to the right of the main altar by Salvi Castellucci; in the same chapel a statue of Christ at the Column (1617) by Niccolò di Smeraldo Salvi da Lucignano; a wooden crucifix above the main altar by Giambologna; a Cantoria sculpted in stone above the door of the sacristy (1546); a crucifix by Francesco Morandini (Poppi), on the second altar to the left. There is a fresco of The Virgin on the Throne with Baby Jesus and the Saints, work of a 15th century Arezzo painter in the small room that leads from the sacristy to the cloister.
Cloister of S. Francesco - Castiglion Fiorentino - ArezzoCloister of S. Francesco
This church was built during the 1600's in the tuscan style. The ground floor is made of semi-circular arches and transept vaults while the loggia of the top floor is made of columns that support the eaves. The severely damaged frescoes in the tympana are by Pelliccione da Colle and represent scenes of the Life of S. Francesco (1627).
Church of S. Angelo
A small necropolis was discovered from the 4th and 3rd e. BC below the floor of the church in the part near the main altar. Part of an Etruscan wall was discovered between the central pillar and the present entrance. This confirms the hypothesis that the church was built on top of an Etruscan temple. The Romanesque crypt of the church is entered from the Municipal Art Gallery, which contains various finds, fragments of a chalice of "bucchero" (black, Etruscan terra cotta), ceramic fragments and pieces of the Etruscan city wall from the Hellenistic period that were discovered during the digs in 1989.


Castiglion Fiorentino: discover the surroundings

  • Cortona Cortona (10 km)
    Cortona was an Etruscan town that today offers many important remains.
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  • Foiano della Chiana Foiano della Chiana (13 km)
    Evidence of Etruscan settlements of the VI-IV centuries BC testify to the ancient origins of Foiano and the nearby town of Pozzo della Chiana.
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  • The Sentiero della Bonifica The Sentiero della Bonifica (13 km)
    Sentiero della Bonifica cycle and pedestrian path which joins Arezzo to Chiusi is about 62 km along Valdichiana equipped for those who wish to travel slowly, either by bike or on foot.
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  • Arezzo Arezzo (14 km)
    Arezzo is set on a steep hill rising from the floodplain of the Arno. In the upper part of the town are the cathedral, the town hall and the Medici Fortress (Fortezza Medicea).
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  • Travel Arezzo Travel Arezzo (14 km)
    A fascinating area that includes Arezzo, Cortona, Bucine, Castiglion Fibocchi and Castiglion Fiorentino.
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  • The Valley of the Chiana The Valley of the Chiana (15 km)
    The Valley of the Chiana is the most vast of the Apennine valleys occupying more than 500 square kilometres of immaculately tended cultivation appearing as a garden from Cortona.
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  • Monte San Savino Monte San Savino (15 km)
    Monte San Savino is the birthplace of the great Renaissance sculptor Andrea Contucci called Il Sansovino and of Pope Julius III.
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  • Lucignano Lucignano (16 km)
    Lucignano is one of the most interesting centres in Tuscany because of its original castle on an elliptical plan, closed in by a wall with towers.
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  • Torrita di Siena Torrita di Siena (23 km)
    The first historical records referring to Torrita di Siena date back to the 11th century when the name appears in an Amiata legal code of the year 1037.
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  • Valtiberina Valtiberina (25 km)
    The Tuscan Tiber valley ( Valtiberina) presents itself to the curious visitor as a huge mosaic of different environments, offering a rich multiplicity ofshapes, colours and perfumes.
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  • Anghiari Anghiari (25 km)
    Anghiari stunning medieval little town on sides of the hills between the Sovara and the valley of the Tiber.
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  • Sovara Valley Sovara Valley (25 km)
    The Sovara valley stretches along the stream of the same name which, after coming down the south-westerly side of the Alpe di Catenaia, runs alongside the group of hills known as Monti Rognosi.
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  • Capolona Capolona (25 km)
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  • Rapolano Terme Rapolano Terme (26 km)
    In the Middle Ages the territory of Rapolano Terme was part of the properties of the Counts of the Scialenga who dominated over the main castle of the area.
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  • Subbiano Subbiano (26 km)
    The history of Subbiano is closely linked with that of the Arno on whose left bank the town developed.
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  • Trequanda Trequanda (26 km)
    The medieval village of Trequanda, crowned by the remnants of the ancient Cacciaconti castle, stands a hill 462 meters high sited between the Val di Chiana and the Val d' Asso.
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Accommodations in the area


    • Montepulciano (Siena)
    • 26 km from Castiglion Fiorentino

    Agriturismo le Caggiole

    Immersed in the verdant countryside around the noble town of Montepulciano, that boasts ancient Etruscan origins, Le Caggiole Estate is perfectly located for exploring Tuscany's most prized treasures.
    In a relaxing and cosy atmosphere uests are offered three comfortable, quiet double rooms with private bathrooms and two comfortable apartments for two persons and for small family groups.

    Availability request


    • Siena (Siena)
    • 49 km from Castiglion Fiorentino

    Agriturismo Marciano

    Agriturimo Marciano : an exlusive opportunity, two holidays at the place of only one. stay in the country and life downtown. Marciano is located near the walls of the Middle Age town of Siena.
    Five confortable double rooms and a suite with a beautiful sight on the Siena Duomo

    Availability request


    • Colle Val D'Elsa (Siena)
    • 64 km from Castiglion Fiorentino

    Relais della Rovere

    The Relais Della Rovere is a charming hotel created from the conversion of an ancient Benedictine abbey and a papal villa of the Renaissance period.
    Set in Colle Val d'Elsa, in the heart of the Chianti area, it is strategically located among Florence, Siena, San Gimignano and Volterra.

    Booking ONLINE


    • Colle Val D'Elsa (Siena)
    • 69 km from Castiglion Fiorentino

    La Pieve

    La Pieve, charming farmhouse located on the hills of Val d'Elsa, between Volterra and San Gimignano, along the Via Francigena, in the heart of the Tuscan countryside, with its luxuriant nature and rich history.
    Framed by olive trees and a wood, it fosters a direct dialogue with nature in complete relaxation where they contemplate and enjoy the stillness in private and unique spaces.

    Availability request


    • San Gimignano (Siena)
    • 70 km from Castiglion Fiorentino

    Agriturismo la Lucciolaia

    In the vicinity of the medieval centre of San Gimignano, nestled in the rolling hills of the gorgeous Tuscan countryside, Agriturismo La Lucciolaia is perfectly located for exploring Tuscany's most prized art towns.
    This ancient farmhouse has been recently renovated and divided into eleven double rooms and two Suites, where the magic atmosphere of past times is perfectly blended with modern comforts.

    Availability request


    • Firenze (Florence)
    • 72 km from Castiglion Fiorentino

    Marignolle relais & charme

    The charming Marignolle Relais & Charme, nestled the hills of Florence, is the ideal solution for those who want a place of excellence and relaxation and love peace and privacy without the amenities of a luxury hotel.
    Marignolle Relais & Charme is especially appreciated by travelers looking for style and tradition by offering deluxe rooms or junior suites in a refined, with superior comforts and impeccable services that make this relais an excellence of Florence.

    Booking ONLINE


    • San Gimignano (Siena)
    • 72 km from Castiglion Fiorentino

    Agriturismo Villa il Palagetto

    Agriturismo Villa il Palagetto located in the vicinity of the medieval centre of San Gimignano, nestled in the rolling hills of the gorgeous Tuscan countryside.
    Provides comfortable accommodation in 6 double bedrooms and two Suites

    Availability request


    • San Gimignano (Siena)
    • 73 km from Castiglion Fiorentino

    B&B la Fornace di Racciano

    La Fornace di Racciano is a lovely Bed&Breakfast a short distance from the historical centre of medieval San Gimignano. It consists of a typical Tuscan country house surrounded by a large flowery garden.
    La Fornace di Racciano consists of seven comfortable rooms and four apartments, two of which are located in the ancient hamlet of Racciano.

    Availability request


    • San Gimignano (Siena)
    • 76 km from Castiglion Fiorentino

    Agriturismo Cesani

    Azienda Agricola Biologica Cesani is an organic farm nestled in the rolling hills of the Tuscan countryside, in the tiny country hamlet of Pancole, 6 km to the medieval town of San Gimignano.
    Azienda Agricola Biologica Cesani is an organic farm nestled in the rolling hills of the Tuscan countryside, in the tiny country hamlet of Pancole, 6 km to the medieval town of San Gimignano.

    Availability request


    • Fucecchio (Florence)
    • 104 km from Castiglion Fiorentino

    Relais Hotel Vedute

    Relais Hotel Vedute Florence surrounded by green countryside is located in a strategic position near Florence, Lucca, Pistoia, Pisa and Siena
    Our Wellness Center & Ayurvedic Thai Aquamor invites you to know Ayurvedic and Thai experience in Fucecchio Florence

    Availability request


    • Castiglione della Pescaia (Grosseto)
    • 109 km from Castiglion Fiorentino

    Villa Roccamare Castiglione della Pescaia 12 beds

    Beautiful and characteristic villa with stone finishes located in the exclusive Roccamare area in Castiglione della Pescaia.
    Surrounded by the green of the pine forest and the total privacy with 2000 sqm park equipped with relaxation area and barbecue is located about 400 meters from the sea and has a private beach.

    Availability request


    • Castagneto Carducci (Livorno)
    • 109 km from Castiglion Fiorentino

    Podere Vignanova

    Podere Vignanova, little charming resort in Tuscany, in one of the more enchanting corners of the Etruscan coast, where vineyards with wines which are conquering the world.
    Surrounded by important vineyards in Castagneto hills the farm holding includes an old country house which hosts 4 comfortable flats and 4 delightful suites.

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    • Castiglione della Pescaia (Grosseto)
    • 112 km from Castiglion Fiorentino

    Villa Punta Ala 9 beds pool

    Beautiful villa with swimming pool surrounded by greenery and tranquility of the exclusive tourist destination Punta Ala and small attic used as service personnel only 300 meters from the sea of Tuscany.
    This ideal solution for those who want to spend their holidays near the beautiful sea of Punta Ala with the comforts of an exclusive villa.

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    • Lucca (Lucca)
    • 126 km from Castiglion Fiorentino

    Historic Villa Lucca 12 beds pool

    Historic villa 14 km from the center of Lucca immersed in the green of the Tuscan vineyards and olive groves, it has a private swimming pool and a large park.
    Set on 350 square meters in a dominant position offers a unique view of the hills of Tuscany.

    Availability request


    • Massarosa (Lucca)
    • 139 km from Castiglion Fiorentino

    Stone Farmhouse Massarosa 8 beds pool

    Stone farmhouse in typical Tuscan style skilfully and elegantly renovated in a dominant position on the hills of Massarosa with spectacular views that reach the sea of Tuscany. The farmhouse has a swimming pool with whirlpool.
    Perfect solution for those that search the real authentic Tuscany staying in the hills but not far from the Versilia sea.

    Availability request



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