Top Tuscan Villages to visit in Autumn

Autumn in Tuscany has a special rhythm: the air is crisp, the light turns golden, and villages reveal their most intimate charm. Exploring small towns in this season means walking through quiet streets, breathing history, and tasting flavors that belong to centuries-old traditions.

One of the most enchanting places to visit in October is Pienza, the Renaissance “ideal city' perched over the Val d’Orcia. Its alleys are filled with the smell of pecorino cheese and the horizon opens onto landscapes painted with autumn colors. Not far away lies Cortona, a hilltop town with Etruscan roots where you can hike ancient paths surrounded by foliage: autumn here means not only history, but also warm meals and local wines. Check out our Hiking Experience in Cortona and find more about this charming experience.

In northern Tuscany, San Miniato becomes the stage for the white truffle festival, where the streets are alive with the aroma of this rare treasure. To the south, Montalcino welcomes visitors with Brunello tastings in its ancient cellars—an experience that echoes what we explored in the blog post Montalcino: A Taste of Tuscany published this summer. And then there’s Anghiari, a small medieval town where artisan shops and narrow alleys create a timeless atmosphere.

Visiting villages in autumn is more than sightseeing, it’s about connecting with a landscape that slows down, with traditions that continue, and with people who open their doors to share what makes Tuscany unique. October invites you to discover villages where history, flavors, and autumn light weave together into an unforgettable journey.

Ready to explore Tuscany’s most charming villages?
Plan your journey with our Curated Itineraries and step into timeless beauty.