Chianti by the white roads

Back in 1716, Grand Duke Cosimo III issued an edict drawing the first official boundaries of Tuscan wine, Chianti included—long before modern appellations. Between San Gimignano and Castellina those borders still read in the land: cypress lanes, dry-stone terraces, fortified farmsteads. The white gravel roads ride over galestro and alberese, the stony mix that shapes Sangiovese. West, the crenellated towers of San Gimignano mark your bearings; south, the Gallo Nero seal points to estates rooted in the 19th century, often on monastic ground.

We collect you from your San Gimignano hotel, then it’s a Mercedes day on the white roads: you taste, we drive. It’s 35 minutes to Castellina for a heritage cellar, another 25 to Panzano for bistecca at Dario Cecchini’s butcher temple, and a final pour near Radda before heading back. With a dedicated driver managing timings and reservations, you glide through appointments and sunset viewpoints, returning just as the towers catch fire with evening light.