This is one of the very first maps I drew, actually the first digital, colour one (done in 2004).
Sorry I don't have WIPs for it, but this is how I went about it:
I used the maps found in various editions of Robin Hobb's Farseer, Liveship Traders and Tawny Man trilogies, copied them on tracing paper and used a scan as base layer (or set of layer), which I put on top with Multiply as blending mode.
On another layer I drew the shape of the land with a hard opaque brush in a bright colour. When this was done I blocked the transparency, filled with green (after filling another layer below with sea-blue) and then started adding different hue variations with a big soft brush with low opacity. I then decided where my light source would be and started working on the details, switching between lighter and darker shades (same for water).
I usually have several other layers for trees, names, roads and borders, sometimes another one between sea and land to adjust the colour of things such as sandy shores, lakes and rivers. On this one I had a layer for sand.
Don't hesitate to ask if you have questions, maybe I'll remember...
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