Requesting Advice - Indleville Map

[Altrunchen]

Introduction:
I am attempting to make a believable city map for a specific municipality in my fictional D&D setting of Kaltamorn. Specifically I am trying to make a map of a city called Indleville but before I start placing buildings and everything I decided to just make an elevation map of the terrain:
Indleville Map (Elevation).jpg

If you can't see the legend on the bottom-right, the darker the area, the higher its elevation. Each region marks a difference of about 50 feet from the lighter regions. The light-blue rim around the coast is where I approximate tidal shifts and everything. Also the scale is: 1 pixel = 8.8'.

City Information:
Est. Population: ~10,000 (give or take a few hundred)
Tech Level: Late Medieval - Mid-Renaissance (Pre-Industrial)
Features:

• Naval Base
• Monastery (on one of the islands)
• Old Castle (used now for administrative purposes; will probably put on the smallest island closest to shore)
• City Walls around city-center

Help Request:
I personally find town and city mapping to be some of the most difficult to execute, with caves a close second. So I would like some advice about where to place buildings, walls, and so on. Does anyone have any ideas about where I should put the various districts, buildings, the city-center, etc?

[XCali]

I am myself busy with a city map. And true words, it is turning out to be one complex map. So, I know how you feel.

What I can offer is questions you can ask yourself:
1. Why did the FIRST people to come to this area chose this place to build something?
2. What did those people build? (A fort, a place to fish, a place to launch their boats. ect.) (Remember, people tend to extend their structures when they settle in. So, where that thing started can have more elaborate structures.

Now, as a city centre develop, a market is build where maybe roads come together, or is the most accessible and those markets have a bit of space for people to sell their wares. There can even be rich merchants that build grander buildings close to the markets they run.

There should be points throughout the city where people go get their FRESH water. Fountains, wells, a river.

As a city get more complicated, there needs to be those who keep the order. Guard towers at key points. Or a barracks or something of the like.
Then you can start thinking of a ruler of the city thinking about having a grander building, so they build it away from a poorer district, somewhere with a desirable trait, like the view or access to something important.


See where I am going, I am building the city from what started it and expanding it depending on what kind of people keep settling there.

For the city I am busy with, the river caused it to be a place where the main road went through and so it became a more important point and this caused things like a need for guard towers and people wanting to live closer to the point.

So keep asking yourself questions, what would certain type of settlers do when they came to the city. The rich might buy up a district and corner it off with a wall, or not.
I hope that helps focus it a bit.

[Azélor]

If my calculations are correct, your map is 5 by 5 miles ? or 25 square miles.
and that is huge unless you intend to map the surrounding countryside and a few villages as well.
A city like this could fit in a area under 1 sq mile.

As too plan a city proper, I don't find it easy either. Xcali post is a start.
Cities emerge at crossroads where there is trade. But at the same time, markets are not necessarily in the center of the town.
You can find a lot of inspiration by looking at old cities, either ones that still exist or based on historical records.

One very defining characteristic of the city is whether the urbanism is planned or not. Most cities were not and many cities today, while having plans for the future, have a lot of constrains they have to work with.

I'd start laying down the main roads. These would be connected to the regional roads and serve as the entry points to the city. There is a good chance the main features of the city will be close to these roads.
Then you might have smaller roads around the city...

Landmarks, public places and other features would be located were streets intersect.

Markets, there would be several of them, spread across the city. Having a unique district center makes no sense in a world where most people travel by foot. There could a unique smaller specialized market but general markets are spread out. Your city would also have buildings and market right outside the city gates. The space being limited inside the city, they tend to spread outside the walls.

And that point can actually be a big concern. Having a wall limits the size of the city and can be seen as a disadvantage. Gunpowder changed the war and defensive walls were not what they used to be.
If the city is near a border zone with another country, the use of a defensive wall can still be justified but if it lies inside the country, maybe not so much.
Some historical cities like Carcasonne in France for example, saw the walled part of the city being abandoned by the wealthy and felt into disrepair and poverty overtime. Until in was restored in the 1800's.