I have Strong Opinions on matters of fantasy cartography. No shock, I know! One of those opinions is that you should never draw to fit the paper. The way I fight that tendency (because it can be really hard not to) is I do a lot of preliminary work on a much, much larger canvas than the target output.
One of the other towns on the same island as Hammondal is called Choragus, and it's not nearly a "city" by any definition, but it's Calembour's only other seaport bigger than a fishing village, and it's got drydocks for ship repairs and shipbuilding, so despite its modest size and relative youth, it's pretty important. I'm just beginning to map it as a kind of brain-break from writing Hammondal's book. The map began like this:
|To Everything, Turn, Turn, Turn|