The primary application I use to create maps, I am pretty much alone in using. I got Del to try it, though. It is Xara Xtreme Pro 3.2 which costs around $250. There is a light version that will do everything you need to create the same type of maps for only $70 - but its not free software.
Although good for only a short time, you can download either version as a fully functional trial (lite is 14 day trial, full is 30 day trial) so you could try out my tutorials, create and save the map for your permanent use ... then buy the app, if you like it.
I have a couple tutorials here using Xara for creating maps...
[Award Winner] Regional Map using Xara Xtreme 4.0
This is probably the tut that will help you most in understanding how to create those kinds of mountains in the first map.