Leave Siena early in a luxury minivan with your guide, and set off to the Chianti hills, enjoying views of beautiful forests, rows of vineyards and pretty medieval hamlets. Your first stop is the walled village of Castellina in Chianti, where you'll explore the town and its covered medieval walkway with your guide. See the fascinating Castle of Castellina, which dates to the 15th century and was built by the order of Lorenzo il Manifico, a popular Florentine statesman in medieval times.

Next, head to the beautiful town of Greve in Chianti, famous for its triangular-shaped piazza and for being the home of famous sailor Verrazzano. Have leisure time here to sample wines (additional cost) or visit the local boutiques and market stalls.

From Greve, you'll take a short drive over to Montefioralle, a village that claims to be the birthplace of Amerigo Verpucci, the famous cartographer who gave his name to the Americas. Enjoy a walk along Montefioralle’s cobbled streets and take in the breathtaking views.

Just outside of this beautiful village is a family-run winery, where you'll enjoy a delicious Tuscan lunch, consisting of cured meats, home-grown vegetables and cheeses, and enjoy a wine tasting of the famous Black Rooster Chianti Classico. While you eat and drink, learn from your friendly guide about the region’s customs and traditions. Then visit another, larger winery, where you’ll be guided through the process of wine production and visit the wine cellars. Hear more about Chianti’s famous red wines, including how they are made and the differences in flavor of the various blends and grapes.

Your last stop before returning to Siena is the beautiful Abbey of Passignano, where you’ll admire the glorious landscapes of the surrounding countryside. The abbey, whose existence has been documented from the beginning of the 11th century, was once one of the most powerful castles of the Val di Pesa.