5. Taormina
Taormina is Sicily’s most popular resort town, and is well worth a trip off the toe of the boot. With sweeping views of two bays and active Mount Etna looming over it, Taormina has a magical, mythical beauty to it. Its ancient heritage is evident in its Greek amphitheater, where world-class concerts and performances are still held today. Taormina’s old Medieval quarter is particularly inviting, with elegant piazzas offering an array of shopping and dining opportunities. Some of the best pasta in all of Italy can be found here.
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.