Meet your guide in the morning and hop in the comfortable air-conditioned minivan for the short ride to Chianti. Gawk at the fabled Tuscan countryside as the rolling grape-vine blanketed landscape, the hills crowned by rustic villas and the tiny ancient villages all unveil themselves before your eyes.
Stop in the walled medieval town of Castellina in Chianti for a short stroll around its narrow cobbled lanes and see the imposing Castellina Castle, an imposing 15th-century fortress, that was built by the order of Lorenzo il Magnifico, from the legendary Medici of Florence.
Hop back in the minivan for the brief journey to the next stop: Greve in Chianti. In the village, take some free time to explore on your own. Perhaps linger in the triangle-shaped piazza or follow the trail of the legendary sailor Verrazzano. Pop into small shops and browse the goods for sale at the outdoor market stalls.
After some time in Greve, ride to Montefioralle, a small town whose claim to fame is that it is reportedly the hometown of the famed Amerigo Vespucci, the cartographer whose first name became the name of two continents: America. Take a stroll around the town and don’t pass up drinking in the incredible views of the Tuscan countryside.
If all that sightseeing has built up a thirst and hunger, stop by a nearby family-run winery next. Sample some locally made wine, including the famous Chianti Classico, and indulge in a lunch of Tuscan deliciousness, from prosciutto to local cheese. Later, visit a second winery: descend into the cellar to sample some more local vino and learn from the winemaker about the particular characteristics of wine from the area.
Before heading back to Siena, stop by the Abbey of Passignano, a gorgeous 11th-century structure that is surrounded by classic Tuscan nature and landscapes.