How to design regional maps.

[MajorScales]

I'm new to making maps trying to design a map at the regional scale (1 inch hexes at 1 mile per hex) for D&D and I have absolutely no idea how to start. Any help on the thought process that goes into making maps like this would be much appreciated.

[waldronate]

WHY are you making this map? That answer will inform everything else that you want to do. I do recommend starting by thinking about at least:
For what use do you intend this map (e.g. practice, general information, board game, RPG campaign, etc.)
Who will receive this map (online users, real-life users, friends, etc.)
What do you want to show (island, peninsula, inland area, lake, etc.)?
How big is your map physically (an 8.5x11 map at 1 inch per hex doesn't cover much area)?
Do you need towns, fields, rivers, lakes, castles, or such things?
How much will labeling play into the importance of the map (are place names critical, will there be political divisions).
What is your intended artistic style (basic hex with one simple symbol in each hex, pretty textures, nice artwork on each hex, and so on).
What is your level of proficiency with tools to make such a map? There are tools all the way from automatic generators that spew maps, tile-based generators that you can use, all the way up to full graphics packages.

[MajorScales]

Thanks a ton for your help.