Yes! I have a broad spectrum of cartography OCDs. There’s two that might be particularly useful here.
Map Like Cities Grow: A place doesn’t start as a city. It’s starts as geography. Start out by creating interesting topography. Make sure there’s water (cities need water), flat land, maybe some trees or hills.
Once you’ve got that, think about how people would move—where would they want to go? Docks, markets, wells, defensible areas, at first, then important centers of culture and government. The routes between these places, avoiding or circumventing terrain, become your major roads.
Also remember for towns with walls, that walls don’t need to circle the entire town, walls don’t always remain useful, and a city doesn’t stop growing just because there are town walls. So only put walls where you need them or covering the most important areas (could be the whole community, but doesn’t need to be, might just be around one community or at one choke point). Don’t be afraid to have a wall running around or partially destroyed, evidence of an old city wall that’s no longer vital (my map of the city of Korvosa has examples of this). Also, always have buildings outside of your walls—it’s probably cheaper to live out there and people are always looking for cheap digs.
No Square Buildings: Unless it’s a shed or a trailer, you are NOT in a square or rectangular building right now. Look at Google maps, think of the shapes of the buildings around you, look at blocks with town homes or Roman insulas. There’s a lot of interesting ways to make buildings look, so don’t let your buildings be boring. You’re going to draw a lot of structures, so don’t try to make them all complex, but think about what types of buildings your drawing as you map.
Those are my big two suggestions! When you put them together, it looks something like this…
I’ve also done quite a few other posts about cartography. You can see a few here:
Wes’s Animated Mapping Process
Sketching a Floating City
Adding Details to Maps
I also suggest picking up the app Skitch for when you’re done. It’s great for adding tags and basic details once you’ve got your worked scanned in.
And remember, you don’t need to be an artist to be a great cartographer. Stick to simple shapes, look at existing maps, think about what your city does and who lives there, and let it inspire you to learn even more about the place you’ve created. You’ll be amazed how many great adventure and characters will come to mind as you sketch!
Hope this helps!