Begin your private excursion with pick-up at your hotel or other accommodation in Siena and drive into the Chianti hills with your guide.
Stop in two of Chianti's lovely hilltop towns in the morning, Castillina in Chianti and Monteriggioni. Enjoy the cobblestone streets lined with shops and restaurants. Admire Monteriggioni's beautifully-preserved Medieval city walls, which have 14 towers.
Travel through vineyard-covered hills to a local farm, where you'll sample some of the area's famous wines – including Chianti Classico – as well as some cured meat made from Cinta Senese. This is a particular pig bred in the area around Siena for its meat. Visit a famous butcher shop for lunch, which includes some typical Tuscan beef dishes.
Continue through the countryside on the famous Chiantigiana Road back toward Siena, stopping in the Medieval town of Volpaia on the way. The last stop of the day is at a wine estate, where you'll enjoy a guided tasting of some of the estate's wines.
Relax on the trip back to Siena at the end of the tour, and get dropped off at your departure point.