Hello everyone

First of all let me please state that in case this thread has a bad history to repeat itself, i'd kindly ask a moderator(or anyone on the forum) to guide me in the already created threads.

So to my question, recently i have developed an obsession towards making maps, and 3 days ago i decided to recreate historical maps of my own country.

The inspiration was mainly this style of map of Poland, where i'd do the maps of countries from the region, but knowing that i'm still a novice and i'd take me quite some time, i decided to make something more simpler. I grabbed a blank map of south-eastern europe, with rivers and all that, and i am stuck and dont know what to do next.

http://i.imgur.com/U9lUgdR.jpg <- something like this only in a smaller region
http://i.imgur.com/4el4sj4.jpg <- First though of how to make in which style
http://i.imgur.com/3NNtkvZ.jpg <- The style i want to make it currently using the same map only blank

Can someone tell me, what is best, Illustrator or Photoshop? Because on the third map i can clearly see its made in Illustrator, but i cant seem to grasp the technique when i try it with another blank map

Thank you and cheers!