For town names, I like to do a combo job. I will pick a culture that I want the current kingdom to resemble. For instance, I have been working on a map, and I view the kingdom as having some vague similarities to the Welsh people, so I looked up a lot of Welsh towns, and simply used names similar to those. I then had some towns that were named in the more "modern" common tongue of the area. A lot of those were people names with some sort of functional name like Boris Bridge, or Wheedon's Crossing.

In addition, what I first did for my world is to create the global map in CC2/3, and then work on the continents from there. I am only doing hand drawn maps on my kingdom level maps. Later on, I may come back and do a hand drawn map for each continent showing a general overview of the continent.