Okay, so I took jbgibson's suggestion to heart and tried something different. I like that a lot better, although it's getting further and further away from that nautical style I was aiming for, but that ways just a means to an ends anyway. All I wanted was something simpler, more informative, and I think this is getting pretty close.

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Notes:
- the compass rose in the bottom right is just a placeholder, as is the box on the bottom left.
- the icons for settlements are still not final, as is their placement.
- same goes for the roads.

I tried a little coloring. I defnitely like the blueish ocean but I'm not certain about the colorized land.

Oh, all textures are courtesy of CG Textures, btw.