Your day starts in Central Florence where you’ll meet your small group of no more than 13 people and expert tour leader. Then you’ll hop into private transportation vans and be spirited out of the city and over to Siena, one of the best-preserved examples of medieval Italian architecture in the world. Spared bombing in World War 2, this time capsule of ancient, precarious-looking buildings is home to the Palio, one of the greatest and most dangerous horse races in the world. Your expert tour leader will immerse you in the unique history and culture of Siena as you explore its narrow streets and admire the breathtaking Siena Cathedral from the outside. Walking the hills of Tuscan towns will make you hungry and thirsty so your next stop is an authentic Italian family farm in Chianti where you will have a behind-the-scenes tour of the vineyards, winery, and wine cellars before sitting down for a sumptuous, all-inclusive lunch made from local, seasonal ingredients. Your meal will be paired with Chianti wines specially selected to perfectly complement the flavors of the dish. After indulging your taste buds, you'll stop at San Gimignano, a town of such unique architectural beauty it has been designated a UNESCO World Heritage Site. Shop for Tuscan culinary delicacies in the rustic, winding streets, or learn about the architectural marvels of the famous medieval tower houses that punctuate the city like sentinels of times long past.