Southern Chianti, Castellina and Radda

That first breath of crushed grapes and warm stone in Castellina in Chianti sets the scene as the low Tuscan light picks out schist walls and Sangiovese rows facing southwest. Leaving Siena on the SR222, you enter Gallo Nero country, the historic mark of the Consorzio founded in 1924. Between Castellina’s Etruscan passageway, Via delle Volte, and the lanes of Radda, soils flip from galestro to alberese, a pairing behind noted crus like Vigna del Nocio or Rancia. On the way back, Monteriggioni—built by Siena in the 13th century—lines up its fourteen towers along the old Via Francigena.

Your Siena-based private chauffeur collects you at the hotel, handles luggage and timing while you taste. A Mercedes stays on call for flexible stops, a table at a working fattoria, and smooth transfers: 30 minutes from Castellina to Radda, another 20 to a farmhouse osteria. You tour cellars as he takes care of gravel roads, stretch your legs on Monteriggioni’s walls, then glide home. No driving, no parking hunts on the SR2 or SP51—just a well-paced day shaped around your tastings.