I draw maps by hand.
I start with the rough shape of the continent (or just the local area, if I'm pressed for time). Then I add in mountains. From the mountains, I draw in rivers. From that, I can consider where forests, swamps, and grasslands would go, as well as putting more detail into the coast where the rivers run into the sea. Given the waterways, I can also draw in major port cities (if any), and then I can draw in roads if the area is settled/inhabited by sentients. I try to imagine what sort of settlements/establishments would form at the crossroads.
Often as I am drawing this stuff, I'm coming up with ideas for the history of the region: how nations and settlements grew and fell over centuries, and how sentient efforts (nations, gods, and/or powerful mortals) affected the topography/geography (creation of deserts as in Lebanon or Easter Island, spell-wracked areas in fantasy settings, areas of fallout in post-apocalyptic settings, etc). Sometimes I start with history, and that affects my drawing, and sometimes it's the reverse.
