
Secret Chianti
Secret Chianti: authentic villages to discover (with a stop in Radda in Chianti)
When you think of Chianti, your mind immediately flies to rolling hills, vineyards as far as the eye can see and cellars where wine flows generously. But beyond the postcard images, this area of Tuscany also holds a more intimate and lesser-known side: that of hidden villages, medieval jewels where time seems to have stopped.
Among cobbled streets, silent squares and artisan workshops, we will take you to discover some secret corners of Chianti, far from mass tourism — with a must-see stop in the splendid Radda in Chianti, the noble and discreet heart of the region.
Montefioralle: a tiny circular jewel
A few minutes from Greve, Montefioralle is one of the smallest and most evocative villages in Chianti. Enclosed by ancient walls and arranged in a circular shape around the old castle, it is a labyrinth of stone streets, flower-filled balconies and views of the valley.
- Not to be missed: the birthplace (perhaps) of Amerigo Vespucci, a walk at sunset and a dinner in one of the local taverns overlooking the hills.
San Gusmè: the beauty of simplicity
In the Sienese Chianti, San Gusmè is a small fortified village that enchants with its intimate atmosphere. Here time passes slowly, among bell towers, old signs and old people sitting on benches. Perfect for those looking for an authentic experience, away from the spotlight.
- Fun fact: every September it hosts a traditional festival that evokes ancient crafts and peasant flavors.
Volpaia: wine and silence among the clouds
Perched at 600 meters above sea level, Volpaia seems to have come out of a movie. It is a perfectly preserved medieval village, inhabited by a few families and one of the most renowned wineries in the area, where you can taste excellent wine immersed in silence and beauty.
Perfect for: an afternoon excursion followed by a panoramic lunch overlooking the vineyards.
Radda in Chianti: the hidden heart that beats strongly
Unlike microscopic villages, Radda in Chianti is a lively but still genuine center, suspended between past and present. Former headquarters of the “Lega del Chianti”, it preserves an enchanting historic center made of arches, stone alleys and panoramic terraces.
What to see: the medieval walls, the Palazzo del Podestà, the Church of San Niccolò.

To experience: a tasting in the Casa del Chianti Classico, a walk at sunset along the “Cammino delle Volpi” path, or a glass of red wine in Piazza Ferrucci.
Radda is the perfect place to stop for a night, savor the slow rhythms and set off the next day to discover new hidden treasures.
A more authentic Chianti awaits you
Those seeking the true soul of Chianti will find it far from the most crowded places, among ancient stones, low voices and infinite panoramas. Visiting these secret villages is a way to rediscover not only the beauty of the territory, but also a more human, slow and conscious style of travel.
And of all of them, Radda in Chianti is the perfect place to start.