Odds are, I am seriously late to this but I have been working on the Dungeonmorph Dice project with Joe and knowing he was the guy behind the Inkwellideas website and I figured out should check out his site. This guy seriously has some major skill creating useful tools for gamers, and lucky for all you Maccies out there, he does it in Java so it is Apple friendly!
The first thing I looked at was Hexographer. I will be the first to admit I have never been a Hex guy, never liked them in the 80s, 90s, whatever you call the 00s and I still don’t really care for them now. However, this is really inspiring, and seeing what others have done is pretty amazing. That said, this product is freaking easy to use..a darn monkey could use it. I threw a handful of maps together (the one to the left is a sample from his site, not my work, but I wanted to show you what can be done with the software).
I am seriously considering purchasing the full license because it is THAT GOOD. If you are looking for a tool to quickly create a overland map for your game and just dont have the time or skill to make it yourself, you really should check this out, I am certain you will not regret it.
The tutorial is very good and a great place to start:
For more samples, see here:
ChicagoWiz just posted his world map he is still working on: