Among the rolling hills of Chianti, where vineyards and olive groves alternate with woods and castles, rise Radda, Castellina and Gaiole in Chianti: three villages united by centuries of history, traditions and breathtaking landscapes. Once the nerve center of the Chianti League, today this Tuscan triangle represents the territory’s most authentic soul, where the medieval past blends with food and wine excellence and a love of nature.
In this ideal itinerary we accompany you to discover the peculiarities of each village, including events, places to visit and outdoor activities signed by WeHike.
The League of Chianti: a medieval alliance of history, wine and villages
In the heart of Tuscany, between Florence and Siena, the League of Chianti, a political-military alliance established by the Republic of Florence to protect and administer one of the most strategic and contested areas of the time. Comprising it were three main villages – Radda, Castellina and Gaiole – organized into terzieri and united by a common statute that regulated their civil, agricultural and military life. Beyond its defensive function, the League also helped to enhance the identity and agricultural vocation of the territory, particularly the cultivation of vines.
The symbol of the Black Rooster, the emblem of the alliance, is still the seal of quality of Chianti Classico, testifying to a deep bond between history, territory and wine tradition. Visiting these villages means retracing the traces of a glorious past and living an authentic experience between culture, nature and food and wine.
Radda in Chianti, the heart of the League
Nestled among the hills, Radda in Chianti was the administrative center of the Lega del Chianti, established in the 13th century by the Republic of Florence to strengthen control of the territory. This historic role is still reflected today in the atmosphere of the village, with its ancient walls and alleyways that throw us back centuries. In addition to history, Radda is a landmark for wine and food events.
In May, the village comes alive with Radda in the Glass, a must-attend event for lovers of Chianti Classico. Between tastings and meetings with local producers, visitors can enjoy an immersive experience among the flavors of the area.
But Radda is not just about wine: it hosts the Chianti Brew Fighters, the area’s only craft brewery. Here, tradition meets innovation, resulting in high-quality craft beers that tell an all-Tuscan story. For an outdoor experience in the area, explore one of our hiking trails in Chianti.
Castellina in Chianti, between Etruscan necropolis and wines of excellence
Castellina in Chianti is also a place where ancient history is intertwined with wine culture. The necropolis of Montecalvario and Poggino, unique archaeological sites and valuable evidence of Castellina’s origins, offer a fascinating journey into the Etruscan past of this area. Strolling through the town, not to be missed is the Via delle Volte, an evocative covered passageway that offers picturesque glimpses and is home to artisan stores and typical establishments.
The highlight of the events, however, is in May, when the village becomes the protagonist with Pentecost in Castellina: Chianti will always be the star, with a side dish of dinners, walks, events and crafts. Still on the subject of wine, Castellina is also famous for its wineries, which produce Chianti Classico of the highest quality.
These include Castello di Fonterutoli, in a charming historic village, and the renowned Cantina Castellare di Castellina, famous for its labels dedicated to birds that change with each vintage. Finally, Fattoria Pomona embodies the authenticity of Chianti thanks to family management and attention to detail. Discover WeHike’s tour dedicated to Castellina.
Gaiole, heroic cycling among the castles
Gaiole in Chianti is distinguished by its atmosphere and events that draw visitors from all over the world. These include the iconic Eroica, a bicycle race that takes place every October and allows participants to ride white roads on vintage bicycles. It is more than a race: it is a journey back in time, an experience of sport but also of getting to know the area and oneself.
Gaiole is also the gateway to the Strada dei Castelli, an itinerary that leads to historic residences such as the majestic Castello di Brolio, owned by the Ricasoli family since 1141 and a symbol of Chianti Classico, or the Castello di Meleto, with its fairy-tale charm, another must-see.
A journey to the most authentic Chianti
Radda, Castellina and Gaiole in Chianti are not just three villages: they are the essence of an area where every corner tells a story, every path offers unique glimpses and every cup holds centuries of tradition. Whether you want to lose yourself between medieval walls, taste the wines of Chianti Classico or enjoy outdoor experiences among castles and vineyards, here you will find an authentic way to discover Tuscany.
