Circle Sea (an old map of mine)
This is a map I drew twelve years ago. I carried it around in my bag throughout my ninth-grade year, which is why it looks a little worn. I always intended to set a campaign here, but now I'm thinking it is a little bit too generic fantasy to be interesting to me thematically. It was made with a sketch of a political and cultural history, as well as a few fantastic elements I thought would be cool (the giant circular sea, the temperate city in the middle of arctic ice, the underwater ruins.)
My style has evolved a bit since then and I think a lot more now about a plausible geological history for the terrain, but I'm still doing things basically in the same way - imagine what the area looks and feels like, sketch out major features, concrete it just enough that I know pretty well what's where.
I like the hand-drawn look because I can imagine the map actually existing in the context of the setting, which isn't to say I wouldn't be open to learning how to polish this up with GIMP or what have you.