La Compagnia del Chianti
The Chianti Region
During the Middle Ages, Chianti was jointly administered by the Provinces of Florence and Siena and fiercely contested by the two rival cities until 1555, when the Medici family established their dominion over all of Tuscany. Defining Chianti’s borders has never been straightforward: only the Chianti Mountains to the east clearly separate it from the Upper Valdarno, while elsewhere the landscape gradually merges into the rolling hills shaped by the rivers Arbia, Elsa, Greve, and Pesa.
Medieval villages, castles, churches, abbeys, monasteries, farmhouses, and noble villas follow one another along an extraordinary itinerary that celebrates centuries of human ingenuity. Over time, the landscape has been carefully shaped by agriculture, creating a harmonious alternation of vineyards, olive groves, and forests—an equilibrium unique in the world.
Visitors are welcomed by an ever-changing countryside, rich in color and atmosphere throughout the seasons. Whether reached by car, motorcycle, bicycle, or public transport, Chianti offers countless opportunities to explore parish churches, castles, and secluded villages—silent witnesses to the region’s remarkable historical and artistic heritage. A stay in Chianti is an invitation to slow down, enjoy the tranquil surroundings, and savor local gastronomic specialties paired with the wines that have made this region famous worldwide.
Tavarnelle Val di Pesa & San Donato in Poggio
The name Tavarnelle derives from the ancient tabernulae, rest stops along the Via Regia connecting Florence to Siena and Rome. The area is rich in noteworthy churches, including San Lucia al Borghetto (13th century), a former Franciscan convent housing a precious 13th-century crucifix and an Annunciation by Neri di Bicci.
Nearby lies Morrocco, home to the Church of Santa Maria del Carmine, originally built in the 15th century, where visitors can admire a glazed terracotta Annunciation in the style of Andrea della Robbia. Not far away stands the ancient Pieve of San Pietro in Bossolo, which today hosts the Museum of Sacred Art, preserving works from churches of now-abandoned villages.
Within the same territory, San Donato in Poggio is a beautifully preserved medieval village, still enclosed by sections of its ancient walls. Highlights include the Malaspina Palace, the Gothic Church of Santa Maria della Neve, and the Romanesque Pieve of San Donato, which houses an exquisite glazed terracotta baptismal font by Giovanni della Robbia.
Along the road from Sambuca to Greve stands the majestic Abbey of Badia a Passignano, founded in 1049 by Vallombrosan monks. Surrounded by olive groves, the abbey resembles a fortified complex and preserves remarkable artworks, including frescoes by Domenico and Davide Ghirlandaio, notably the celebrated Last Supper.
Greve in Chianti
Strategically located at the crossroads between Florence, Siena, Valdarno, and Valdelsa, Greve developed in the 13th century as a market town serving the surrounding castles. Its heart is the distinctive Piazza Matteotti, triangular in shape and framed by elegant porticoes. The square still plays a central role in local life, especially during the annual Chianti Classico Wine Fair held each September.
Overlooking the town is Montefioralle, a medieval village that retains its original urban structure. Nearby are several historic castles, including Verrazzano, Vicchiomaggio, Uzzano, and Lamole. Just outside Greve lies Villa Vignamaggio, traditionally believed to be the birthplace of Mona Lisa.
Castellina in Chianti
Once a feudal stronghold and later fortified by Florence, Castellina played a key defensive role against Siena. The medieval fortress dominates the town, while the evocative Via delle Volte, a covered walkway built into the town walls, offers striking views through ancient arrow slits.
Just outside the village is the Etruscan necropolis of Montecalvario, featuring monumental tombs dating back to the 7th–6th centuries BC, evidence of the area’s pre-Roman origins.
Radda in Chianti
Historically positioned on the frontier between Florentine and Sienese territories, Radda was the seat of the Chianti League, an autonomous jurisdiction established in 1250. The town preserves portions of its medieval walls and towers, while the Palazzo del Podestà stands out for its façade adorned with coats of arms.
Nearby, the Romanesque Pieve of Santa Maria Novella is notable for its richly decorated capitals, featuring animal and symbolic motifs unique in the Chianti region. A short distance away, the charming Castle of Volpaia enchants visitors with its narrow lanes, historic palaces, and the Renaissance Church of Sant’Eufrosino.
Gaiole in Chianti
In the Middle Ages, Gaiole was an important market center along the route to Valdarno. The surrounding countryside is dotted with castles and parish churches, reflecting a long tradition of agricultural prosperity. Among the most impressive fortifications are Vertine, Meleto, Barbischio, and especially Brolio Castle, rebuilt in the 19th century at the behest of Bettino Ricasoli.
Nearby are the Romanesque Pieve of Spaltenna and the serene Abbey of Coltibuono, founded by Vallombrosan monks and set amidst ancient fir trees.
Castelnuovo Berardenga
Marking the southern edge of Chianti, Castelnuovo Berardenga originated as a feudal settlement in the 9th century. Though little remains of the original town, the elegant Villa Chigi Saracini, overlooking the village with its expansive park, is a highlight of architectural interest.
San Casciano in Val di Pesa
Founded under the authority of Florentine bishops, San Casciano became an important fortified center in the 13th century. Traces of medieval walls and towers remain visible today. The Museum of Sacred Art, housed in the Church of Santa Maria del Gesù, displays outstanding works, including paintings attributed to Coppo di Marcovaldo and Ambrogio Lorenzetti.
Other notable landmarks include the Collegiata, the Church of Mercy, and several historic parish churches scattered throughout the countryside. The area is also renowned for its villas, such as Villa Tattoli, Villa i Collazzi, and Villa Bossi-Pucci, known as Albergaccio, where Niccolò Machiavelli once lived.
Impruneta
Inhabited since Etruscan and Roman times, Impruneta became closely linked to Florence during the Middle Ages. The spiritual heart of the town is the Basilica of Santa Maria, founded in 1060 and long revered as an important Marian sanctuary. Though transformed over the centuries, the original Romanesque crypt remains intact.
Inside the church are works by artists such as Michelozzo and Luca della Robbia, as well as a venerated icon of the Madonna, traditionally attributed to Saint Luke. Adjacent to the basilica, the Museum of Sacred Art preserves centuries of votive offerings, manuscripts, and precious metals.
Impruneta is also world-famous for its terracotta production. The distinctive cotto dell’Impruneta has become an iconic element of Tuscan architecture and is exported internationally, symbolizing the enduring craftsmanship of the region.
