I'm trying to create an illustrated map for a friend's wedding. Most map tutorials I can find are for technical maps and I would like to find a resource with tips and tricks for designing more illustrative, design maps. Examples below:
These are all hand drawn/painted. You won't really find many tutorials on how to draw something as specific as a map. Just look for general drawing tutorials.
It's honestly just a matter of picking up a pencil and start drawing it.
There are no magic buttons or tutorials to draw something for you.
While seconding Scott's "There's no magic button," what I did when I had to create city and country maps was to find an actual paper map, scan it, and trace it in Illustrator. That gave me a good realistic grid. From there I could simplify the map, pretty it up, tweak streets, add icons, etc.
If you want the hand-drawn look, buy the paper map and use tracing paper or a lightbox so you can trace the original.
This tutorial from Smashing Magazine seems relevant: