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I probably would have suggested you to make the plan first before flattening lol

What was your reason for flattening instead of working with the natural landscape? I think the answer to that is where you should start basically. But in general I would say start with a rough idea of what you want for the river and then the cliffs (just in general). Then focus on smaller areas.
 
I agree that one should plan a general idea of what they want before flattening. Though, this gives you lots of room to experiment with. I'd probably start with the river mouths and what you want to do with them. Whether that's making a lake or connecting them somewhere. After that, I'd start from the airport entrance to resident services to the rest of the island. It really helps to see other islands with a similar theme you want to do as well.
 
I'm doing my town right now. I thought long and hard about how to do it...and I decided against flattening the whole thing. I started with the bottom left corner, moving a couple of my main buildings...and I'm going from there. So far, it's going surprisingly well. I think I would have been overwhelmed if I flattened the whole thing. So...I don't know. I just wish you luck with that. Lol.
 
figure out where you want to put your villagers and shops first; then where you want to put the rivers and mountains. if you breed flowers then now is a good time to get the flowers that you want in your town *because of the flat areas*. you can only have 8 bridges in town too so where you put everybody and the shops is pretty important lol
 
Figure out where your shops and villagers will be, personally I liked shops together and then villagers in there own community.
 
I'd say start around resident services, and move outwards from there, if you don't have a theme yet find out what you want, after that make a notepad for everything you want to build on your island, could be anything, a beach bar, a bike shop, a mountain, a giant lake, anything you want, after that you can start thinking about how you want to place them, and have them flow together.
 
From your earlier posts (although your idea might've changed), you said you wanted a natural look. So, when I began designing my island, I looked at top down view of real life towns/cities and some in-game towns/cities.

One of the ideas I looked at was Pokemon towns. Obviously you can't mimic one exactly but it could also help plan out shrubbery or trees. It gives you the pipeline for your paths. It can be just temporary and then you can alter it later on.
 
If you're really stuck, maybe check out other people's towns/maps? That usually helps me.

Fortunately, the dream suite makes it pretty easy these days!
 
honestly, just choose a random spot and go from there

iirc, I think I placed my rocks first, followed by my main waterways. then buildings and paths, then general decor trees etc. lastly general touch-ups and slowly working on parts not the main island section
 
you should definitely take a screen shot of
your flattened map and plan out what you want where.

Are you going for a more symmetrical look? if so on your map you can map out where you want your residentials and shops to go.

If you’re going for a literal town theme kinda island then maybe align your resident services and shops kinda close by and then move on to other areas?
 
We have online island planners to help you design. This one is the most popular:

 
I like to watch tours of other people’s islands for inspiration!
 
I think I'd consider myself more of a spontaneous person and generally cannot plan out every inch of my island/town as I prefer things to unfold more naturally as ideas/inspirations come to me. So for me, I start with areas at the entrance and townhall first. This is because both the airport and townhall cannot be moved, so there's no chance of me having to redo everything later because of how I regret building placements. Then from there, I like to tour islands via dreams or look at Pinterest to see if there's any general theme/builds that interest me, and if yes, I will try to either recreate that or come up with something similar that fits the map of my town. One important thing to note is pace - I make sure to only work on one area of my town at any given time so I don't overwhelm myself. Hope this helps.
 
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