As you can see, I completely redesigned the layout from the original sketch. I had a few problems with it, but by far the biggest was the fact that it was crap. I like this one much better and I hope you do too.
The second picture is the sketch of the island layout with a basic description of what’s on what’s on each island. These are pretty broad strokes, but I’m going to start figuring out the details next. I’ll decide what the various buildings will be, make a few edits to accommodate some things, then start drawing all this at a 5′ (1.5m) grid scale. I’ll draw one island at a time rather than all at once and I’ll post each one when it’s finished. When all the linework is done, I’ll scan everything and start coloring.
The layout above isn’t carved in stone yet, so if you have any thoughts about the map or what might make it better, by all means let me know. Or if you’ve got any questions, feel free to ask!
I would expect a separate fish market next to the fishing docks, and the main market could easily go right up to the docks for ease of trade.
Please consider swapping the internal fort and manor so the fort overlooks trading ships in case any become a problem. Also rich manor owners tend to look with distain on ordinary traders and smelly dockworkers.
Finally, the passage into the main harbor seems narrow and twisty. As long as ships fit through that can actually be an advantage, as visiting ships need to hire a local pilot to get them through, so it is hard to sneak things in.
I actually expect there is a lot of smuggling going in through the fishing docks.
There will be a separate fish market by the fishing harbor. I think the fort is good where it is. The only entrance to the harbor for large ships is through the lifting bridge in the center and the fort is meant to cover that passage.
I’d say you’re right about the smuggling.