Hey, some people asked me to tell how I dray my city maps (see images).
Usually I start thinking of the geography: where there're mountains, or just hills, where there're rivers and seas. But I don't draw them directly, I start making the downtown (usually European ones, America downtowns are ... boring). I don't know wheter there will come suburbs, where freeways come - I just start to draw (all by hand, except for airport runways). After some suburbs or neighbourhouds you decide that you created a huge traffic problem (that's the 'fun' in real cities: having an old centre which you might not change, so: how to solve the problems without spending to much in tiny streets?). Eventually, you can design some new district which do are planned.
Of course it isn't difficult to forget the facilities like ports, marinas, business areas, sports areas etc. But you really need them, without them it's just a structure on paper, not a 'real' city.
1. start thinking about a new map (take your time, a week or something)
2. outline the geography and main infrastructure (roads, railways+main stations and airports), though, only in your head! You do can draw the coast lines if you want, and parts of rivers that borders the area you're drawing at the moment.
3. start at an other blank part and make some newer neighbourhoods
4. When you made some neighboorhoods, start thinking where you want to have suburbs, business areas, industrie harbours etc. as well as the main roads.
5. Proper old cities often have traffic chaoses, due to the increase of traffic since ca. 1900 (the roads weren't build for cars, however, the suburbs do). So create a efficient road system, but draw the excerpts you need for the next parts of the map.
Fill up the clear areas with neighboorhoods, if there're at the edges make some ugly appertment buildings too - after WOII they needed some quick and cheap houses. Also universities and hospitals took new buildings at the edge.
6. As you can read, I like cities with a lot of history (old downtown with tiny streets, appertment buildings after WOII, workers houses surrounding the centre. And note: often the railway stations are not that close to the centre!
7. Fill the tiny leftovers with schools, sports areas, business complexes etc.
8. Every city boasts something (something you're proud of, like a high light hosue, a nice church, a remarkable mountain top, a vivid fishing harbour, lovely parks etc. Make you're cities unique! (so choose sometimes flat areas (Holland) or fjords or something.)
I usually don't write on the maps themselves, but on transparent paper. Sometimes I create names, sometimes I don't. I often use the following names: Zuve, Nemme, Ceëntra, Bodde, Fluwe, Vlinsterloo (pronounced in Dutch they sound less weird than in English, I'm ensured), sometimes some Dutch words for the wheater phenomens.
My maps usually take 10-12 hours to draw.