Tips on creating an isometric mountain town

[Lillzzaa]

I've been requested by my friend to create a map of her fictional mountain town and I'm struggling to figure out how to map it out. I can't seem to find any examples of isometric mountain town maps for reference.
Are there any tips on how to draw a city that is nestled within mountains? How do you put down villages around hills? I've tried drawing mountains around landmarks but it doesn't seem right. Any advice is appreciated!

[Wingshaw]

I've tried on many many occasions to capture the feeling of a town spreading across steep slopes, and I know it's very very difficult. The best suggestion I can offer you in terms of the design/layout is to look at Italian hilltowns, like Riomaggiore, Montepulciano and San Gimignano.

As to how to map it effectively, I hope you find a good method and share it, because I'd love to get some inspiration for how to solve this problem myself...

Wingshaw

[Chlodowech]

So... i had some 30 minutes of time to kill, and heres a quick attempt that i made and some thoughts that i came up with during its creation

This is the rough hill shape i started with. As to what i‘ve experienced with this and other towns, detailing the shape before drawing the town is unnecessary double work, unless you need a really specific shape.

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I always start with the very bottom row of houses, which mostly defines the hill shape by its layout. The very convenient thing is that the overall perspective is not too important since buildings won’t feel odd when they’re set a bit „too high“ in relation to their context, the terrain and its slopes can excuse almost everything.

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After the bottom row was done (ofc i had to add a church) i just kept stacking further rows of buildings on top of each other, mostly at parallels, and some oat different angles where i wanted to give the impression of a little square (above the church). Here it helps to give each row a thicker back line to establish a bit of a system in the mess of houses.

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In the end, i put a fat castle on top. It’s not ultimately necessary, and in this case it was mostly random, but it helps to create a feeling of distance when one or a few structures break the skyline of the background.

And that’s when i called it done - i hope i could be of help with this.