Tuscany Landscapes, Castels & Chianti Wine District

About this tour

This six-hour loop from Florence traces the ancient Cassia Vetus through Chianti's heartland, stopping in the medieval villages of Greve and Montefioralle before arriving at a working wine estate for lunch. You'll taste three Chianti Classico vintages and estate olive oil alongside a farm-to-table meal prepared from produce grown on the property, guided throughout by a professional wine expert who explains the region's heritage and terroir.

Highlights

• Drive the Roman Cassia Vetus through vineyard-quilted Tuscan valleys
• Explore Greve's central piazza and connection to Renaissance explorer Verrazzano
• Wander 12th-century Montefioralle's intact stone lanes and ramparts
• Learn the Black Rooster legend tied to Chianti Classico identity
• Taste three estate Chianti Classico wines with professional guide
• Compare extra-virgin oils from the property's own groves
• Eat lunch made entirely from the estate's organic harvest

What to expect

Your driver collects you from your Florence hotel and heads south into rolling countryside. The first stop is Greve, where you'll have time to walk the arcaded square and take in the quiet of a working Tuscan town rather than a tourist setup. Montefioralle comes next—a steep, narrow village frozen in the 12th century, best explored on foot through its stone passages. The final three hours happen at the wine estate: a guide walks you through the vineyards and winery, explaining how Chianti Classico is made, then you sit for lunch with three wines and an oil tasting. Food is simple, seasonal, and sourced from what grows here.

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