The tiny city-state of Citta di Scarlino
From a recent Burning Wheel game set in a milieu riffing heavily on quattrocento Italy, wherein the new-money della Spada family spars with the old, established Nicolosios. See also any number of Shakespearean works.
The map itself is a sort of odd shape because of Obsidian Portal's reliance on a square format for its map uploads. It's done entirely in Photoshop CS4 with the aid of an Intuos tablet. The fonts are, um. Monky Business, and another whose name escapes me. The pattern overlay is a desaturated snapshot of some frost on a windowpane (for people like myself who are obsessive collectors of interesting pattern tiles, ask and I'll send it along) and meant to imply a sort of parchmenty feel without being yet another transparent crinkled grocery bag.*
I stipulate the northern quarters of the city are kind of empty: I wanted to evoke a little bit of Rome, where entire neighborhoods went to ruin over the course of the city's life and were subsequently renewed, sacked, ruined, rebuilt, and so on. At this scale, foundation lines or debris piles were indistinguishable from the buildings or lots so I left 'em off. Commentary cheerfully accepted.
*Edited to add: Not that crinkled paper is a bad thing. I just tend to fall back on it too often when a map feels like it needs more texture.