I've had good luck getting a watercolor-ish look with gimp by running a blur, then a filter called gimpressionist that simulates brush strokes, then *just* enough blur to get rid of the actual brush lines. At least one of the people I showed a map to said "hey, that looks like you used watercolors!"
One tactic to try, anyhow.
You can also use the brushes that people have posted around this forum (Wag and Star Raven have done a few) to make a more hand drawn map. And just to confuse you a bitRobA also has a few brushes in his sig that you might want to look at
To follow up on GPs suggestion about more info on the style you are looking for, I think the best way to discribe it would be to show it in a map. Post a WIP and use the suggestions that will follow to help refine the style. I am quite sure that you will recieve enough C&C to get you there, along with some techniques on how to do it as well.
An Welcome to the CG
Art Critic = Someone with the Eye of an Artist, Words of a Bard, and the Talent of a Rock.
Please take my critiques as someone who Wishes he had the Talent
Here are some that I've found. It is in general a very classical style. Possibly even earlier style than this as well. I might see what I can find from earlier periods...
1500s era map of Hungary
http://www.stockmapagency.com/zoomif...HUNG-16CEN-ANT
Other examples
http://www.floridahistory.com/us@1544.html
http://www.worldmapsonline.com/histo...-jerusalem.htm **This one is close, I'm not so keen on the quasi-isometric view, but that sort of thing**
(A bit too old, and I don't think I would be good at the tapestry-figures)
http://www.henry-davis.com/MAPS/LMwebpages/235E.html
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