I am a HUGE cartophile and started drawing maps when I was about 6. The main reason I started running games was to share all my worlds with people. Most of my maps are hand-drawn, but my later ones are usually a rough hand-drawing and then traced over and touched up digitally. Here are some of my favorites:
Set in region that was once a lush bay, the changing climate and rapidly receding seas turned the bay into a giant salt flat. The brown border at the north indicates a massive mountain range that is effectively impassible and the blue border at the bottom is the current coastline of a super-salt saturated sea. The color range on the settlements indicates density: black = dense urban, dark brown = less dense city or dense town, light brown = town or village, pale brown = scattered houses and hamlets.
The Sundered Veil
One of coolest games I ran, the conceit was that the Mage Guild in their arrogance tried to get closer to the source of magic in the Astral Plane, but unwittingly ripped a portion of the world out of the material plane and into the void. The spell killed most of the mages and the recent sacrifice their lives trying to reverse it. However, all they managed to do was put a bubble around patch of earth to protect it. So the map is the whole of what got pulled out. Because it is so self-contained and detached from every other plane, powerful enough entities started to become gods and the players eventually became gods as well. The colored circles are regions where a new plane is budding (i.e. a plane of water in the south and a plane of Hell in the center.
Probably my favorite map to date, the Sun Lands is obviously a Africa/Sahara/Egypt-inspired map…except in a world with dragons…and psychic scarab beetle-people. Always try to make “realistic” terrain and climate zones and the transition from lush rain-forest to desert with mountains radically shaping those climates is of particular interest to me.