Umbar

Umbar, built by the Numenoreans at the height of their power, the landing place of Ar Pharazon during the campaign against Sauron, strong hold of the Black Numenoreans after the Drowning, and later, of the Corsairs.

Umbar spent most of the third age locked in an ongoing Rome/Carthage-type conflict with the Gondorians. Toward the end of the age it served as the rallying point for legions of haradrim and fleets of pirates in service to Sauron.

I always pictured Umbar (being an important port for the Numenoreans) as one of the great cities in middle earth; older, stronger, and probably more magnificent even than the later cities founded by the Elendil and his sons, Annuminas and Osgilitath (and far surpassing the gondorian fortress cities like Minas Tirith or Dol Amroth)
we see only very little of the city here, which i imagine to be a big, populous city, and a bit of a sprawler aswell. In addition to ancient Carthage, more than a little of Istanbul, a high watermark for human architectural history (and a city of many historical parallels to Umbar) that I had the distinct pleasure of spending some time in back in '09, found it's way in here. I like to think that, like real cities and historical sights of incomparable importance (cairo, tehran, and istanbul, at one time) it is considered greatly lamentable by the gondorians that a great achievement of men like Umbar is inaccessable to them because of current geopolitics.
I may end up doing one of those areal images, with a view of the whole broad, meandering harbor, fortified in key places, and houses, towers and palaces climbing the hills to reach the Great Pillar raised to commemorate Sauron's defeat and humiliation at the hands of men. (that's if i feel like driving myself crazy)