Boarding your air-conditioned coach in Florence, you will meet your tour leader who will stay with your group for the duration of your day trip. As you journey through the rolling hills, vineyards and olive groves of the Chianti region, they will tell you what to look out for in each new town. Your first stop will be the medieval town of Siena, where the Palio horse race has been held twice a year since the 17th century. A local guide will join you for a tour through the red-brick streets to the Duomo di Siena. Exquisitely faced and floored with marble, this grand cathedral also houses sculptures by the young Michelangelo. Take the time to breathe it all in, before your tour continues to the Piazza del Campo. It is at this exact location where twice a year, jockeys representing Siena’s wards compete fiercely (and not always fairly) for glory. As you listen to your guide’s tales of victories and defeats, it will be easy to imagine the piazza filled with the thunder of horses hooves. Back aboard your coach, you will spot the iconic tower houses of San Gimignano on the skyline from miles away. This Medieval walled town will be yours to explore, as you wander back in time along the narrow streets, being able to ask your tour leader where to find the best gelato. After enough free time to explore and take pictures, rejoin the group for your complimentary glass of Chianti wine and some nibbles. The coach will then return you to Florence.