Labels and icons are an interesting aspect of cartography to me. What I've been going for lately is having transparent regional labels, which allow the viewer to see more of the terrain, mixed with solid icons for settlements, whose locations and natures (city, town, capital) are more important than the relatively small amount of space they take up.

I like the look of the solid icons, but you make an interesting point. Perhaps I could give them less of a dropped shadow? I'll think on it.