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

Castellina in Chianti

The centre of Castellina in Chianti built up area is the ancient fortress designed in the second half of the fifteenth century by the great architect Giuliano da Sangallo.


Castellina in ChiantiCastellina stands more than protected on its hilly bed. The village offers a series of patrician palazzos which are restored military garrisons built first by the associates of the counts Guidi who, originally from Garfagnana , pressed forward into the heart of Tuscany in the attempt to control it either diplomatically or militarily, and later by the Florentines who were constantly on their guard against the Sienese. The centre of the built up area is the ancient fortress designed in the second half of the fifteenth century by the great architect Giuliano da Sangallo.
In Via Ferruccio one gets the feeling of Castellina’s former opulence. Right at the end of this street, at the fork leading to the fortress, is the neo-Romanesque church of San Salvatore, rebuilt after being destroyed in the second world war.
A stop-off in Castellina may obviously include tasting at the numerous wine lodges, but you can also get to know the great art of Chianti pork-butchers whose charcuterie is highly prized for its unforgettable flavours.

Rocca di Castellina in ChiantiIf we want to find the origin of Castellina in Chianti we have to go far back to the beginning of history. These hills, sometimes wild, often softly rolling, still indicate that mankind has been using them for differenl purposes at least since the 7th century B.C. Towns and settlements founded during this period and located along the most important donkey tracks leading from the mountains down to Castellina in Chianti, are stil] proof of a communication link between the large Mediteranian Etruscan cities like Vulci, Vetulonia and Roselle, as well as the famous tradin' centers of the North like Spina.
Since the 1 3th century A.D. Castellina is part of the "Lega del Chianti", meaning "Chianti Alliance". This was a administrative and military alliance within the state of Florence. Because of its optimal strategic location which guaranteed the control of all surrounding roads, as well as the whole valley of the Elsa river, Castellina retained its military position.
Proof of this is the existence of the imposing fortress, nowadays used by the local town govemment. Castellina was once surrounded by mighty walls and smaller towers, only two gates intermpted the closed defence line. One pointed towards Siena, the other towards Florence. Unfortunately both gates were completely destroyed (the gate towards Florence was destroyed during battles in the second World War). Parts of the defending walls can shall be seen today. Unfortunately most parts have been covered over or been integrated into the later construction of houses.
In 1483 Castellina was once again retumed to the Medici. Due to the surrender of Siena to the troops of Karl Vin April 1555 and the following ammexation of the State of Siena, Castellina in Chianti lost its strategic importance and became a part of the dominion of the Grand Duchy of Toscany.


Castellina in Chianti: discover the surroundings

  • Chianti museums Chianti museums (7 km)
    Chianti museums: Museo di Arte Sacra of Impruneta, Basilica di Santa Maria of Impruneta, Museo di Santa Maria sul Prato of San Casciano val di Pesa, Museo di San Cascinao
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  • Chiantishire Chiantishire (7 km)
    The Chianti territory with its hilly countryside of incomparable beauty lies in the heart of Tuscany.
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  • Radda in Chianti Radda in Chianti (7 km)
    Radda in Chianti is the vineyard village. From the high ground on which it was built in the middle ages, between the waters of the rivers Arbia and Pesa, you gaze over a very dense interweave of vineyards.
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  • Monteriggioni Monteriggioni (10 km)
    Monteriggioni is without doubt one of the most classical and best known Italian walled town.
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  • Poggibonsi Poggibonsi (11 km)
    Poggibonsi rises nearby the confluence of the Staggia torrent in the Elsa river, along the valley dividing the region of the Chianti by the Colline Metallifere.
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  • Staggia castle Staggia castle (11 km)
    The walls of Staggia castle in Poggibonsi join the castle on the northern side and are today almost intact, with the exception of two short interruptions.
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  • Brolio Castle Brolio Castle (12 km)
    The Brolio castle has a Longobard origin, although today of the ancient original small fortress remain only the location.
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  • Meleto castle Meleto castle (12 km)
    Like in a fairytale, the Castle of Meleto stands out in the enchanting Chianti landscape at the end of a nice avenue lined with cypress-trees and junipers, in the middle of sun-kissed fields and vineyards.
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  • Gaiole Gaiole (12 km)
    Gaiole in Chianti has developed along the valley of the River Massellone due to its idea position as a trading and meeting point and its origins are based in these very geographical characteristics.
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  • Barberino Val D'elsa Barberino Val D'elsa (12 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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  • Montefioralle Montefioralle (13 km)
    The village of Montefioralle is probably one of the most ancient in Chianti and is still today enclosed within its original walls.
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  • Greve in Chianti Greve in Chianti (13 km)
    In the ancient times, Greve in Chianti was a small built-up area of the territory called "Agro di Florentia", even if expert and researchers of the Etruscan civilization claim that it can date back to a previous century.
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  • Colle Val D'Elsa Colle Val D'Elsa (15 km)
    Colle di Val d'Elsa is located in the heart of Tuscany, in a strategic position, close to the cities of Siena, Florence and Volterra, along the route of the old Via Francigena
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  • Valdelsa Valdelsa (15 km)
    Val d'Elsa is located in the heart of Tuscany, in a strategic position near the cities of Siena, Florence and Volterra.
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  • SentierElsa SentierElsa (15 km)
    The way down is located to the left of the bridge of San Marziale, as one stands with one's back to Colle di Val d'Elsa.
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  • Siena Siena (17 km)
    Founded by the Etruschis, Siena was Roman colony to the time of August.
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Accommodations in the area


    • Colle Val D'Elsa (Siena)
    • 14 km from Castellina in Chianti

    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


    • Siena (Siena)
    • 16 km from Castellina in Chianti

    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


    • San Gimignano (Siena)
    • 18 km from Castellina in Chianti

    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


    • Colle Val D'Elsa (Siena)
    • 20 km from Castellina in Chianti

    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)
    • 20 km from Castellina in Chianti

    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)
    • 21 km from Castellina in Chianti

    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)
    • 23 km from Castellina in Chianti

    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)
    • 31 km from Castellina in Chianti

    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)
    • 54 km from Castellina in Chianti

    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


    • Montepulciano (Siena)
    • 57 km from Castellina in Chianti

    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


    • Castagneto Carducci (Livorno)
    • 66 km from Castellina in Chianti

    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


    • Lucca (Lucca)
    • 77 km from Castellina in Chianti

    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


    • Castiglione della Pescaia (Grosseto)
    • 86 km from Castellina in Chianti

    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)
    • 86 km from Castellina in Chianti

    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


    • Massarosa (Lucca)
    • 88 km from Castellina in Chianti

    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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