6. Siena
Brimming with Gothic architecture and artistic masterpieces, the medieval town of Siena has also been declared a UNESCO World Heritage Site. It is set on three hills and is one of the most scenic cities in all of Tuscany. Many people try to time a visit with the summer Palio festival, an age-old horse race that runs around the central shell-shaped piazza. Il Campo is dominated by the red Palazzo Pubblico and its Torre del Mangia tower. Climb the 500 steps and be rewarded by idyllic views of the town and surrounding Chianti countryside.