That's looking pretty good! If it were me, I think I'd leave the settlement density where you've got it, but add in things like roads, important sites (mountain peaks, shrines, fortresses, ruins, etc) to help fill things out. That way you get a lot of world-detail/depth, and you don't have to go into quite so much naming detail.

As far as the labels themselves, I can't say I'm a huge fan of the way you've got them overlapping the coasts. In some places you clearly have to, like with Porto Saxeo, but with others, like Paculeto, why not just move them up or down a few pixels?