Palermo, Sicily, Italy
Palermo is a city of contrasts and most people either like it or hate it. It's a place that's ugly and pretty, thick with smog but surrounded by mountains and the blue/gray sea, with a good number of public gardens. On one block are impressive Arab-Norman buildings and on the next crumbling facades and heaps of trash. (More commonly, cruise ships that call at the island will anchor at Giardini-Naxos on the south side as it is the gateway to the splendid Taormina.)
Located on the northwestern coast of the island of Sicily, the city was founded by Ancient Greeks and eventually became part of the Roman Empire. In the ninth century, the Arabs took over and converted churches to mosques and the common language to Arabic. The Norman period followed, and in the 13th century Palermo was the capital of the Holy Roman Empire. The French and Spanish later passed through. Today, while Sicily is officially part of Italy (the regional government is semi-autonomous), its capital city of one million residents feels neither European nor Arabic, but some combination of the two.
The city was heavily bombed by Allied Forces during WWII, and some neighborhoods have yet to be repaired. More recently Palermo has made headlines as the base of the infamous Cosa Nostra (mafia).
To be sure there are rich neighborhoods (check out the shops on Via Liberta, Palermo's Rodeo Drive) and poor neighborhoods, sometimes on the same street. If you wander just a little off the beaten path you will find streets that just don't seem safe even in broad daylight (visitors are advised not to wear flashy jewelry and to keep close watch on their cameras, pocketbooks and wallets).