I have started an illustrator file and added a few odd shaped rectangles spaced in haphazard but organic distributions to stand in as buildings. Coast is on the left hand side (west coast) and the lord's house is in the north. There is a boatyard which needs to be relatively near the water, and since it is a fishing town, I figure there needs to be some sort of fish buildings on shore. Cleaning sheds, storage sheds, smokehouses, etc. Maybe a single magical ice chest?
At the heart of every great fantasy epic is the hero's journey. But how epic would it really be if he walked a straight line on a plain for 3 months? Worst. Journey. Ever. Where you are is almost as important as what you are doing in fantasy, and as the creator of the world it is your job, nay, your duty to make it interesting and unique.
Towns have begun springing up in the region of my map known as Enchera. It is the focus of the first part of my Wickfire campaign, where the PCs start out. The goal of the campaign is to deck out "their" city, Lurais with all the goodies they could want, giving them access to items and services and influence they would not normally have. The game is definitely cumulative. There are quests they are working on that take place over the course of several dungeons, for instance.