Separated from mainland Italy by the Strait of Messina, this thriving town is a harbor sitting at the northernmost point of Sicily's Ionian Coast. It is home to the Norman Messina Cathedral, with its Gothic portal, 15th-century windows and an astronomical clock on the bell tower. You can wander around Messina through its wide boulevards and elegant buildings and discover its art museum and its tormented history, which includes a devastating earthquake in 1908 and a mass bombing in WWII.