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

The Valley of the Chiana

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.


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, the old city which dominates it from its height of 600 m. Already 22 centuries ago it must have been considered the granary of Etruria since Hanibal, before crossing it to draw the Roman legions into the ambush at Trasimeno, was able to supply his troops by sacking it.
Valdichiana - Copyright Giuseppe Toscano
But more than the evidence recorded by historians, are the archeological remains and the cultural traditions which reveal the Val di Chiana as the land of ancient civilisation. The hypogean tombs of Camucia and Sodo, the remains of Farneta, the museum of Cortona, confirm that the Etruscans populated and cultivated this valley battling with the forces of the water which for thousands of years had swamped it.
When Leonardo, more than 15 centuries later, designed his “Codice Atlantico”, the Val di Chiana appeared again as a lake. That is why, on the fall of the Western Roman Empire, the Barbaric invasions and mainly the Gothic wars which stained Italy with blood for almost all of the VI cent., depopulated the countryside. No longer carefully attended, the land was once more invaded by the waters.
The Lorena reclamation, at the beginning of the XIX cent., designed and directed by the Aretine Vittorio Fossombroni, restored its ancient fertility to the valley, re-establishing villages and farm houses, wonderfully designed, and, for a time, extraordinarily functional.
It was not always, however, an isolated paradise.
After Hanibal, other epic historical events took place in the valley during the process which brought about the establishment of the Tuscan State. The Battle of Pieve al Toppo (1288) in which the Aretines inflicted a tough defeat on the Sienese, who were at the time allied with the Florentine Guelphs, and the battle, called Scannagallo (1554) because of the large number of mercenary French soldiers killed, which took place near Foiano and determined the subjection of the Republic of Siena to Cosimo de’ Medici, First Grand Duke of Tuscany. Many extraordinary geniuses of art were born here amongst the most famous of whom are Luca Signorelli, Pietro da Cortona, Andrea Sansovino, and in our own century, Gino Severini. The Autostrada del Sole and the Rome-Milan railway line cut the valley lengthwise. Two state roads, the Umbro-Casentinese and the eastern branch of the Cassia, following the curving line on both sides, provide excellent connections with the larger centres while a dense network of good provincial roads allows for the crossing of the valley in all directions and for the discovering of the most beautiful spots.
The Val di Chiana was the granary of Etruria and is still today the only area where the most prized breed of cattle is raised, the Chianina, which is derived directly from the pre-historical “bos primigenius” . This agricultural vocation characterizes the economy of the valley, where activities connected to cereal crop production, sugar beet, quality oil production and a typical wine “Bianco Vergine”, prosper.


Valdichiana: discover the area

  • Castiglion Fiorentino 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.
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  • Cortona Cortona
    Cortona was an Etruscan town that today offers many important remains.
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  • Foiano della Chiana Foiano della Chiana
    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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  • Lucignano Lucignano
    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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  • Monte San Savino Monte San Savino
    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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  • The Sentiero della Bonifica The Sentiero della Bonifica
    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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Accommodations in the area


    • Montepulciano (Siena)
    • 24 km from Valdichiana

    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)
    • 34 km from Valdichiana

    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)
    • 49 km from Valdichiana

    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)
    • 54 km from Valdichiana

    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)
    • 55 km from Valdichiana

    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)
    • 57 km from Valdichiana

    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)
    • 58 km from Valdichiana

    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)
    • 61 km from Valdichiana

    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


    • Firenze (Florence)
    • 61 km from Valdichiana

    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


    • Fucecchio (Florence)
    • 92 km from Valdichiana

    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


    • Castagneto Carducci (Livorno)
    • 94 km from Valdichiana

    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.

    Availability request


    • Castiglione della Pescaia (Grosseto)
    • 96 km from Valdichiana

    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


    • Castiglione della Pescaia (Grosseto)
    • 99 km from Valdichiana

    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.

    Availability request


    • Lucca (Lucca)
    • 114 km from Valdichiana

    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)
    • 126 km from Valdichiana

    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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