In this post I will describe the process I am currently using to draw maps. I started with a Pangea type supercontinent for my world as follows. I decided that this would split apart and rotate indicated by the blue arrows. I indicated tropical and arctic regions for the continents.
Next I redrew them one at a time adding more detail and modifying the land masses a little since this is after many millennia.
Next I divided the map into a number of smaller parts to zoom in on.
Next I draw this region at high magnification. First I rough it in with colored pencil, blue for water, olive green for the edges of the hills. This is from the north side of the lake. Then I go over the edges of the water with a pencil and rough it in for example the small island on the right. Next I go over the pencil with a fine marker. I am leaving many gaps along the way as shown on the peninsula in the center. Then I can add more detail as shown in the shore on the left. Sometimes I may just connect the shore and leave it smooth. These gaps are also helpful if a river needs to connect to the shore or if you need to put docks or a city next to the shore. Next I look for a good spot for a city. When I want to put a city in I use a triangle to add some vertical lines and some 30 degree lines so I can draw an isometric city. The vertical lines are supposed to help my towers from looking crooked.
Next I add more detail to the shore line. Look for natural structures and add small lines to make them look more like three dimensional objects. Choose a direction for the sun, mine is usually above and to the right, and use a larger marker to outline the opposite edges, for mine it is the bottom right edge of the shores, for kind of a drop shadow. Add some waves along the water. Next use a dark olive green to create some structure for the shoreline. I try to make it look kind of like hills or streambeds. Then color this in with light olive green. Finally I go over anything close to the water with a brighter green color. Usually I don't start coloring until all of the pen work is finished.
For cliffs start with a jagged line. Think in terms of isometric shapes and be sure to add quite a few zig-zags. Then draw lines coming down from the cliffs. Keep adding more lines and curve outward a bit, put in a few vertical jogs. Color in shadows with a dark brown in the corners of the cliffs. Add some color to the cliffs, purple, brick red, brownish orange, dark yellow, grey etc. Go over with a light yellow or white to burnish them in if you want.
For the river draw single jagged line going up into the hills. Leave plenty of gaps. Add a second jagged line. Start filling in the gaps. Don't forget to add some bridges, foliage, islands, and lakes along the river. The two banks of the river will be similar but different.
To color in the hills I start with dark brown in the shadows and some pale yellow on the sunny side. Add light brown lightly to blend the other two colors, finally burnish with pale yellow or white if you feel like it.
To draw hills start with sort of a rolling ridge line in pencil. Then add some hills with pen and start shading the shady side of them. Add some forests next to the hills and some outcrops in the forest.
