Chianti Classico Trail

The Heart of Tuscan Wine Country

Walk the ancient trails connecting medieval hilltop villages in the Chianti Classico zone, where the Sangiovese grape reigns supreme and every vista is a painting waiting to be discovered.

What’s Included

• Three-day guided walking tour through vineyards and olive groves
• Visits to five prestigious Chianti Classico DOCG producers
• Tuscan cooking class with a local nonna
• Two nights in a boutique agriturismo surrounded by vines
• All meals with expertly paired wines

The Journey

From the ancient walls of Castellina in Chianti to the cobblestoned streets of Radda, each day brings new landscapes, new flavors, and new stories. The pace is deliberately slow — this is Slow Italy, after all.

You’ll learn to distinguish the terroir differences between sub-zones, taste vertical vintages from acclaimed producers, and understand why Chianti Classico has earned its place among the world’s great wine regions.