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Castelfiorentino is situated in an optimous position on the Chianti hills, in the heart of Tuscany.

CastelfiorentinoCastelfiorentino represents Valdelsa's natural crossroads.
It is situated in an optimous position on the Chianti hills, in the heart of Tuscany.
In the last few years the town has witnessed a great increase in its population, so much that it has become an important reference point for the area's tourist trade economy. This is exactly why Castelfiorentino's local administration decided to dedicate to tourists this section of its web-site, making it easier for them to find their way around the town.
Our territory goes proud of its numerous significant masterpieces, such as the frescoes attributed to Benozzo Gozzoli, the Church of S. Verdiana, Oliveto Castle, not to mention the many aristocratic villas built in the areas of Meleto, Granaiolo, Cambiano, Cabbiavoli and Montorsoli noted for their historical and architectural value.
Therefore we are happy to present this web-site to all of you, in the hope that it may contribute to maintain alive a love and attachment for this community and its surrounding territory.

Far back in 1149 the name of Castelfiorentino was given to a castle erected along "Via Francigena" (the road used by pilgrims and waifarers, in the Middle Ages, on their way to Rome from the north of Europe), on the site where the Roman settlement of Timignano once stood.
Enclosed within the fortified castle, set upon a hilltop, was the parish church of Sant' Ippolito (the ancient parish of San Biagio); erected within a second ring of the walls were Borgo d'Elsa and Borgo Nuovo.
There were also gateways and towers and two roads which met in a crossroad on the only square present (today' s piazza del Popolo). Ruled firstly by the feudal governors, the Cadolingi and then by the Alberti Earls, the centre was subsequently passed on to the Bishop of Florence during the XII century. This caused conflicts between the Church and the Empire and the powers of Siena and Florence, during this period Castelfiorentino became an important military out-post of Florence. It became the headquarters of a podesta' (mayor) and was awarded the privilege of having a red lily on its flag and the title of Castelfiorentino.
Peace was declared between Siena and Florence after the Battle of Montaperti in 1260. After a brief period of peace, the town became a battlefield full of raids and violent attacks. Infact, in 1521, during a violent attack by the Spanish troops, Castelfiorentino was totally demolished. Therefore the importance of its strategic position diminuished, even though Albert Cosimo I restructured its fortifications. Even its administrative importance became limited due to its dependence on the vicar of Certaldo.
The town blossomed again during the XVIII century, under the leadership of the Grand-duchy of Tuscany, and became the home of the court clerk and the mayor's office, with a municipal guard and a much wider jurisdiction over Certaldo and Montaione.
Following the almost unanimous plebiscite vote, Castelfiorentino happily embraced the Kingdom of Italy becoming the district's chief-town in 1868. It was one of the first country to elect a socialist administration in 1902.

Visit Castelfiorentino : Santuario di Santa VerdianaVISIT CASTELFIORENTINO
The large, tree-lined Piazza Gramsci presents itself as an obligatory reference point. There you can see the Teatro del Popolo (Town Theatre), built in the XIXth century. Beyond the centrally situated Piazza Cavour, we arrive to Via Palestro where we find the building of the "Arciconfraternita di Misericordia" (Archbrotherhood of Mercy), built in the thirties. Going forward, we can see, on the right, the Church of S.Francesco, built in the XIIIth century. Behind S.Francesco, at the end of a vast tree-covered field, stands the Church of S.Verdiana restored at the beginning of the XVIIIth century. Coming back to Piazza Cavour, on the right, and taking Via Garibaldi and the steep Costa (Via Ferrucci), the only remaining gate of the ancient town wall can be seen. On the right, along Via Lungo le Mura you can see the ruins of medieval buildings. Once Piazza del Popolo is reached, the Palazzo del Comune (Town Hall), rebuilt after a fire in 1544 and restored in 1867, can be seen on the left. Opposite stands the church of SS. Lorenzo and Leonardo, built between the XIIIth and XVIth century. Following Via S. Ippolito on the left of the church and climbing the steps opposite, we get to the top of the hill (panorama) where the Parish Church of SS. Ippolito and Biagio stands. it was built in 1195 in brick with ceramic decoration on the facade. On the back a long stretch of the early town wall and the remains of two towers can still be seen. Coming back to Piazza del Popolo, round the corner of the Town Hall we get to the medieval Via Tilli. At number 41 we find the Town Art Collection that contains the frescoes and sinopias of Benozzo Gozzoli executed between 1484 and 1490.

The countryside around Castelfiorentino, a suggestive mild hilly landscape, is also rich in interesting historical and artistic monuments.

From Piazza Cavour, crossing the bridge over the Elsa river, turn right and take Via Sanminiatese. Passing through Dogana, a small village once municipal border, we come to a site called Madonna della Tosse, where we can see the Chapel frescoed by Benozzo Gozzoli and his co-workers in 1484. Now the frescoes can be found in the Town Art Centre. Taking the road on the left we come to Castelnuovo d'Elsa, dominating the valley, where remains of the early town wall and medieval construtions can be seen. Nearby, about 3 Km away to the south-west, you find the Parish Church of Coiano, a typical example of Tuscan Romanesque. On the way back to Castelfiorentino, passing through Castelnuovo d'Elsa, follow the sign to the Villa of Meleto. After visiting the villa, cross again the Elsa river and take the 429 State Road, along which the Villa of Granaiolo can be seen. It was built at the beginning of the XVth century on the ruins of an ancient fortification. Heading back to Castelfiorentino, we pass through Cambiano, where you can admire a XVth century beautiful Villa and the Church of S. Prospero, of which documentation exists as far back as 863.

At the crossing between Viale Potente and Viale Zanini, follow the signs to Renai. Running along a winding road, after a steep slope, we arrive to the Pieve Vecchia, the earliest settlement of Castelfiorentino, from which we can have a delightful view of the town. Heading forward, we find the farm and the Villa of Cabbiavoli. Nearby you can see also the Villa of Montorsoli, surrounded by a beautiful park. Further on you come to the Piangrande where you can find the Castle of Oliveto, of notable historical and artistic interest. Two km far from there take the 429 State Road back to Castelfiorentino.

The Francigena trail is a medieval route that linked Canterbury to Rome, millions of pilgrims in the past travelled to Rome walking on this route. It has had a fundamental role in the construction of the European identity, relating the local religions, cultures, habits, languages and economies of several countries of the old continent. At the beginning of the second millennium in Europe there were a multitude of pilgrims looking for the purification of the spirit.
This route attests the importance of the pilgrimage in Middle Ages period: the pilgrims had to make this travel walking (for penitential reason) with a distance of 20-25 km for day. Moreover they did not travel isolated but in group and carried with them the standards of the pilgrimage.
The Francigena was also a way of intense commercial exchanges and at the same the armies passed on this route for their movements.
Our territory was crossed by the Francigena Trail, it helped the birth and development of many localities in the Valdelsa. In fact, during seven centuries, kings, emperors, religiouses and common people walking southwards on the Via Francigena stopped in Valdelsa.
Their path ran along the current town of Gambassi Terme, Castelfiorentino, Certaldo, Poggibonsi and San Gimignano; from here pilgrims continued to Siena and to Rome.
However, Via Francigena is not a "road" as actually we know: it's a "bundle of paths" running along the same direction and crossing near bridges, poorhouses and villages.
Pilgrims arriving in Valdelsa stopped at Pieve di Chianni's poorhouse (Gambassi Terme), at Pancole and at Pieve di Cellole.
Then they walked along the river Elsa as far as Poggibonsi and went up San Gimignano, crossing the centre of town and continuing their journey to Abbadia a Isola and Monteriggioni, as far as Siena.
Since 1994 the European Council has recognized the ancient Via Francigena as "Cultural European Itinerary" belonging to "Historical European Itinerary".
On 2000, jubilee's year, modern pilgrims come back to ancient route.

Castelfiorentino: discover the surroundings

  • Montaione Montaione (7 km)
    The town of Montaione is in the province of Florence, but it is at an equal distance from all the most important cities in Tuscany.
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  • Monastery of San Vivaldo Monastery of San Vivaldo (7 km)
    The monastery of San Vivaldo is certainly bound up with a succession of the Franciscan's Office leaving here a notable trace.
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  • Certaldo Certaldo (9 km)
    Certaldo is divided between its medieval walled town on a hill and the modern residential and industrial suburb spread out below.
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  • Montespertoli Montespertoli (10 km)
    Montespertoli in ancient times, the Etruscans inhabited these lands, but Latin place names are mostly reminiscent of the numerous Roman settlements that flourished here.
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  • San Miniato San Miniato (13 km)
    San Miniato is located along the Via Francigena that connected northern Europe to Rome during the Middle Ages and it was travelled by an uninterrupted flow of men, armies, trade, ideas and culture.
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  • Montelupo Fiorentino Montelupo Fiorentino (15 km)
    Montelupo Fiorentino, as the name suggests, is situated just a few kilometres from Florence itself.
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  • Montelupo Ceramics Montelupo Ceramics (15 km)
    The production of archaic maiolica in Montelupo dates back to the second half of the 13th century.
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  • Capraia e Limite Capraia e Limite (15 km)
    The built-up area of Capraia maintains the structural characteristics of a fortified medieval village with its strategic position on a steep knoll.
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  • Palaia Palaia (16 km)
    Palaia is an agricultural zone situated on one of the highest ridges that divides the valley of Arno from the Valdera.
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  • San Gimignano San Gimignano (16 km)
    San Gimignano rises on a hill (334m high) dominating the Elsa Valley with its towers.
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  • Barberino Val D'elsa Barberino Val D'elsa (18 km)
    A winding hilly road, once the ancient Via Cassia and now State road n° 2, leads up to the town of Barberino Val d’Elsa, situated high up above the valley.
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  • San Casciano Val di Pesa San Casciano Val di Pesa (18 km)
    Situated to the south of Florence, San Casciano is surrounded by the neighbouring Communes of Scandicci and Impruneta.
    Read more
  • Cerreto Guidi Cerreto Guidi (19 km)
    Cerreto Guidi, a hilly territory, situated between the Montalbano and Arno, owes its name to the Counts Guidi, an ancient feudal family who built a castle not far from the route Francigena.
    Read more
  • Montalbano Montalbano (19 km)
    The Montalbano landscape is dominated by hills with grapevine cultivation occurring in the plains or on terraced fields, olive trees spreadingover the higher areas.
    Read more
  • Fucecchio marshes Fucecchio marshes (19 km)
    The Fucecchio Marshes cover an area of about 1,800 hectares, divided between the Provinces of Pistoia and Florence.
    Read more
  • Fucecchio Fucecchio (19 km)
    The Salamartano hill in Fucecchio offers a beautiful view of the Valdarno Inferiore from the plain with many villages to the hills of Le Cerbaie, until Serra mountain and the Apuan Alps.
    Read more

Accommodations in the area

    • San Gimignano (Siena)
    • 12 km from Castelfiorentino

    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

    • San Gimignano (Siena)
    • 16 km from Castelfiorentino

    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

    • San Gimignano (Siena)
    • 17 km from Castelfiorentino

    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

    • Colle Val D'Elsa (Siena)
    • 24 km from Castelfiorentino

    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

    • Firenze (Florence)
    • 25 km from Castelfiorentino

    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

    • Greve in Chianti (Florence)
    • 34 km from Castelfiorentino

    Villa Chianti 7 beds

    Villa Chianti is a private villa for rent in Chianti area with pool and garden that can accommodate up to 7 people.
    An oasis of peace and tranquility with views of the Chianti valleys not far from the main tourist attractions of Tuscany.

    Availability request

    • Siena (Siena)
    • 41 km from Castelfiorentino

    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

    • Bagno a Ripoli (Florence)
    • 46 km from Castelfiorentino

    Villa Valdarno 12 beds

    Villa Valdarno is a typical Tuscan farmhouse located in a secluded and peaceful area in the heart of the Tuscan countryside, among vineyards and olive groves, and enjoys a privileged panoramic view of the Florentine Valdarno.
    The ideal solution for groups of friends or acquaintances who wish to spend their holidays in Tuscany with the comforts of a detached villa with swimming pool and large garden.

    Availability request

    • Lucca (Lucca)
    • 48 km from Castelfiorentino

    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)
    • 58 km from Castelfiorentino

    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

    • Viareggio (Lucca)
    • 60 km from Castelfiorentino

    Villa Torre del Lago 5 beds

    Typical Tuscan farmhouse for rent in Torre del Lago, Massaciuccoli area with 3 bedrooms and 5 beds, just 1 km from the Tuscany coast.
    Ideal solution for small groups or families looking for a villa for rent not far from the sea in a context of absolute privacy.

    Availability request

    • Massarosa (Lucca)
    • 62 km from Castelfiorentino

    Farmhouse Massarosa 14 beds pool

    Beautiful ancient Tuscan farmhouse completely renovated located on Tuscan hills 10 km from the golf course of Versilia. The villa can accommodate up to 14 people.
    An oasis of peace for those looking for a stay in the Tuscan hills while staying close to the sea. Perfect for a relaxing holiday in close contact with nature.

    Availability request

    • Camaiore (Lucca)
    • 62 km from Castelfiorentino

    Charming villa Tuscany coast 14 beds pool

    Eighteenth-century villa located in a picturesque area of the Tuscan hills at the foot of the Apuan Alps, the villa has a park with swimming pool and tennis court.
    The spacious suites of the villa embellished with charming details and enhanced by modern comforts will make your stay an unforgettable experience.

    Availability request

    • Camaiore (Lucca)
    • 63 km from Castelfiorentino

    Villa Pieve di Camaiore 8 beds pool

    Luxury and charming villa with swimming pool for rent surrounded by the green hills of Camaiore not far from the sea of the Tuscan coast.
    The villa is ideal for those looking for an oasis of absolute peace and relaxation guaranteed by the elevated position and the external fence in style.

    Availability request

    • Camaiore (Lucca)
    • 63 km from Castelfiorentino

    Villa Prato di Sopra Camaiore 10 beds pool

    This villa is really some thing special, perched on the top of a hill the views are endlessly breath taking.
    This villa is really some thing special, perched on the top of a hill the views are endlessly breath taking.

    Availability request