Castelvecchi and the Medieval Secrets of Chianti

Chianti Castles, Churches, and Legends

In the beating heart of Chianti, where the hills unfold in a mosaic of vineyards and cypress trees, lies an ancient soul of towers, walls, and silence. This is the Chianti of castles and churches, a land that for centuries marked the border between Florence and Siena, the scene of battles, love affairs, and forgotten stories. Among the many villages that preserve this past, Castelvecchi, in the Radda in Chianti area, stands out as a timeless jewel, capable of still evoking the most authentic medieval Tuscany.

A village steeped in history

Castelvecchi is more than just a village: it is a small universe suspended between history and legend. The first traces date back to the 10th century, when the area was dominated by watchtowers and fortresses defending the roads. Today, strolling among its ancient stones and the surrounding rows of vines, you can still sense the echoes of that past: the wind seems to whisper the tales of pilgrims, monks, and the lords of Chianti.

The heart of the village is dominated by a perfectly restored architectural complex, where the historical memory and the area’s winemaking tradition harmoniously blend. From here, the gaze sweeps across the hills, almost losing the boundary between sky and earth—a panorama that alone is worth the trip.

Wine as a common thread between past and present

Castelvecchi is also a spiritual place for wine lovers. The Castelvecchi cellar, ancient and evocative, preserves barrels and aromas that recount centuries of winemaking tradition. Here, a Chianti Classico is born that seems to encapsulate the very history of these lands in its glass: intense, elegant, with notes of red fruits and spices that evoke sun and stone.

Visiting Castelvecchi means enjoying a complete sensory experience: guided tastings, walks through the vineyards, and stories of family and the land. It’s a return to the essentials, where every sip is a memory and a discovery.

Stop 1 – Brolio Castle

About a half-hour’s drive from Castelvecchi, Brolio Castle, the imposing fortress of the Ricasoli Barons, dominates the hills with its fairytale elegance. Its origins date back to the 11th century, and over the centuries it has been the site of several battles between Florence and Siena. Today, you can visit the castle, stroll through its scenic gardens, and discover the legendary cellar where the original formula for Chianti Classico was born. A must-see for those who want to combine history and wine in a single glance.

Stop 2 – The Parish Church of Santa Maria Novella

A few kilometers from Radda is the Parish Church of Santa Maria Novella, one of the most beautiful examples of Romanesque architecture in Chianti. Its golden stones recount nearly a thousand years of faith and art: the simple and solemn interior preserves 14th-century frescoes and an enchanting atmosphere of tranquility. It’s the ideal place for a quiet break, immersed in spirituality and the landscape.

Itineraries among churches and legends

The surrounding area of ​​Castelvecchi offers ideal itineraries for those who enjoy slow and mindful tourism. The dirt roads connecting the villages reveal glimpses that seem painted, while the silence of the woods invites you to stop, breathe, and listen.
And if night falls among the vineyards, it’s not uncommon for legends to resurface: it’s said that gentle spirits still roam among the ruins of the old Chianti manors, guardians of a past that refuses to fade.

A Chianti to be discovered slowly

Castelvecchi and Radda in Chianti represent the essence of a Tuscany that cannot be grasped quickly. It’s a place to savor slowly, perhaps at sunset, when the hills turn golden and the scent of freshly poured wine mingles with the cool evening air.
A trip here is more than just a visit: it’s an encounter with history, beauty, and time that seems to stand still—just like in a medieval dream that Chianti jealously guards.