Mapping Dungeons & Dragons

Creating a setting for Dungeons & Dragons usually starts with creating a map. Creating the largest overview possible of a world first seems to make things slot into place afterwards. "Oh, there's a mountain here? Well, then it makes sense to have that harbour town here..." It fills in little details, that can often spiral into much grander things.

So it's rather interesting to read that to create a good map, you need to take the opposite approach, as detailed in What Makes a Map Good.

People preferred schematic route maps that showed the relevant paths and places to turn, even if directions and distances weren’t accurately depicted.

It even goes as far as to mention you should heavily distort information, in order to provide it in such a way that people can use it. That's perfect of course when using a map editor like Wonderdraft. Forget about adding all the information. Just start with the most exaggerated version of your own world and let the details flow naturally.

Hand the map to your players et voila, they'll start filling in the blanks for you with their own ideas and expectations. Either use or subvert those and add the details in your own personally maintained copy. Within a few sessions you'll have a great living world to rummage through.