Big fan of wilderness hex maps, especially with numbered hexes. They let you turn the outdoors into a place of adventure equal to the dungeon if you populate the locations - locations of lairs, dungeons, farms, interesting landmarks, magical fountains, waterfalls, shipwrecks you name it.
I even had a set of hexmapper icons I'd created, set up with a bit of whitespace at the bottom for four digit numbers, but lost them when I reinstalled my operating system and didn't back them up. Will have to recreate them again, sooner or later.
As for the alternative....for the most part, I've found that a gridless wilderness map is a fairly sure sign of DM running an almost completely empty and featureless wilderness, where it's just a place for wandering encounters to happen until you get to a dungeon or city. Present company exempted, of course.
In a continuation of the "world as dungeon" theme, allowing population of wilderness by breaking it down into discrete areas, I'm trying to figure out a way to map urban areas in a similarly convenient fashion as we do dungeons (square grids, broken down further into discrete and numbered rooms and corridors) and wildernesses (hex maps with numbered hexes). The best I've come up with is just to use square grids, but a 90 degree angle city feels artificial in a way that hexmapped wilderness and gridded dungeons don't.
Any ideas on how to conveniently map urban areas without resorting to vector-based mapping, which is notoriously fiddly and carries the same location population problems of a gridless wilderness map?