Sicily
Never go against a Sicilian when death is on the line!—Vizzini, The Princess Bride
OK, that's not true (it didn't work for Vizzini). If Italy is a boot, then Sicily is the football.
Once part of the Magna Grecia and of the Kingdom of Sicily, the island of Sicily has its own dialect, a slightly different culture (like all other 20 regions in Italy) and special autonomous status in Republican Italy (like five other regions in Italy). Sicily's position at the "neck" of the hourglass-shaped Mediterranean Sea has made it a coveted strategic location and the island has seen more then it's fair share of war and been transferred from power to power. In World War II, the Allied entry into the island was what caused Italy's Face Heel Turn and Benito Mussolini getting booted out of power. Occasionally it has seen a time of independence or near independence notably under the Medieval Norman Kings.
Historically, home of The Mafia.