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I've decided to draw maps, on these maps, I planned on drawing regions which already have determined areas (ex. Region 1 has 30.000 km²), the problem is, how would a measure a region's area on a map? Some territories have some pretty wild shapes, with many islands, which makes it very difficult to measure its area by common means. So I resorted to (bear with me) pixel counting, needless to say, that didn't work out too well, especially on bigger maps.
So I came here to ask if there's any program, app, or technique at this point, to draw lands whose size's have already been established?
Edit - I plan on drawing multiple territories, each with set areas, on the same map, so I can't draw one region and calculate it's area (on the map) then change the scale of the map so it would fit that one region's (actual) area, because it wouldn't fit the other ones.

EDIT (from JBH): The "duplicate question" does not address the question of cartography software at all. This isn't a duplicate question, but it's closed, so it can no longer be answered. However, it's worth providing a simple link to help out people interested in software for drawing maps. Visit the Cartographer's Guild list of mapping software, where you will find a great many pieces of software both paid and free. Cheers.

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    $\begingroup$ You can find a few techniques here: worldbuilding.stackexchange.com/questions/89920/… $\endgroup$ – Willk Apr 22 '18 at 1:05
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    $\begingroup$ @Willk That's enormously useful, thank you. $\endgroup$ – Jedboo Apr 22 '18 at 1:20
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    $\begingroup$ @TCAT117 A lot of people actually do care about building a world that make sense. We have a lot of these people on this site. $\endgroup$ – Vincent Apr 22 '18 at 1:46
  • $\begingroup$ Although, as I browse around, it might be worth your while to look here. $\endgroup$ – JBH Apr 22 '18 at 17:31
  • $\begingroup$ I am not aware of a software that can do specifically what you are looking for. You will have to draw the shape and tweak it gradually until it has the desired size. I would recommand using the Gimp, it is free and more intuitive than other soft. Real GIS soft are maybe better at this but unless your already comfortable with them, Gipm is a better option. $\endgroup$ – Vincent Apr 22 '18 at 18:24
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Download free AutoCAD or ArchiCAD - these will allow you to have free trials or demonstration versions which will allow you to import an image such as a scan of your countries.

Trace over the country and islands with a polyline (Autocad) or zone (ArchiCAD) and use the measure command (AutoCAD) or simply Get Properties (ArchiCAD) and it will calculate and give you the area. In ArchiCAD you could even give each zone a name, and it would automatically collate the areas for you in a list to get each countries total area.

Modern CAD programs are 'unit flexible', so you could use Kilometres, or millimeters or any unit of measure. Prior to doing the above, put a 'scale bar' on your sketch that is a certain length, so you could proportionally scale the image on the CAD program to give you the correct figures.

These programs are adept at handling tens of thousands of shapes, to any level of detail, so no matter how complex your map is it is possible to get an accurate result. As an example:

enter image description here

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  • $\begingroup$ Definitely, an answer I was looking for, thanks a lot! (I didn't know that Autodesk made these types of programs though) $\endgroup$ – Jedboo Apr 25 '18 at 0:56
  • $\begingroup$ If you use AutoCAD, go to Preferences... Units. This allows you to change from m (default) to km. $\endgroup$ – flox Apr 25 '18 at 2:15

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