Hey, so I'm working on a map, and I have a couple issues I'd like advice on. I'm working in GIMP 2.8.

First off, the raw terrain--no embellishments. I feel like the coastlines need some help, but I can't put my finger on what it is. Any thoughts? If you have any comments on other elements as well, I'm all ears.
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Secondly, the countries and their borders, as they sit presently. I can't come up with good names, so those will come later. I'm having trouble figuring out how to distinguish several polities over multiple landmasses without having obnoxious color fills as it is now. If I divided things up more in some areas like I would like to, colors would become very difficult to tell apart. Is there something more elegant I can try?
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Final question, fonts. The era of this map is high medieval/early Renaissance, but Gothic type fonts clash pretty severely with this map style, in my opinion. Is it better to simply present it with more modern fonts, maybe something formal and serif as a compromise?