here are some samples to help you out.

Port Warden map should be a simple layout like this Obsidian map:
http://www.cartographersguild.com/at...4&d=1242904647

I don't have many thoughts on the city, other than it should be fairly organized in terms of layout, have a keep and outer wall, docks area with plenty of berths. Outside the wall there should be some sort of "shantytown" called nicknamed Bogtown that is rundown and less organized and smaller in scale.
Of course anything extra works too.

For the "explorers map" I have in mind something like this lovely island map, though I understand this is a prime example and probably more work than what we're talking about here. The one difference is that the areas near Port Warden would have all this detail, but the further you get from Port Warden the details should fade away into vagueness. (as those areas haven't been explored as much). Example:
http://www.cartographersguild.com/feature/SheguMap.jpg

For the continent main map, I was thinking something like this:
http://www.cartographersguild.com/sh...?t=1774&page=3

Again, this is mostly to get a sense of the basic features of the land and not so worried on placing a bunch of individual features (such as towns/cities) on it. But if it conveyed topography and features such as forested/savanna/jungle/mountains/hills then it would work perfectly.

Again, if I'm asking for too much, let me know. I don't know how much work these styles require. And I'm certainly flexible as long as the finished product works for what I need it for.