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Hard to explain. But: I am in the process of creating a stylized map of a small country in the North-West of Europe ;-)

So, basically, I want to create the picture on the right from the picture on the left:

enter image description here

Now, I've done this before and it can be done using Illustrators Pen tool, clicking point after point using SHIFT to force 45º angles.

But I wonder:

Can this be automated? Jazzy vector in, straight vector out

or,

Is there any program offering any tool that allows me to do this while using a continuous drawing tool like Illustrators 'pencil' tool?

And, any help in re-formulating this question is also much appreciated :)

EDIT Thanks all for your elaborate answers! I can tell you spend quite some time in composing. But I notice I did not phrase my question question clearly enough. Yes, I can use the pen-tool-with-shift in AI or a grid, in Inkscape. But what I would like to is to draw freely (no pun intended) — as if holding a pencil — while my hand is being restrained to only draw at 45º angles (0º, 45º, 90º, 135º … 315º). Metaphorically, of course.

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    I can recommend a very useful Illustrator Plugin called VectorScribe. astutegraphics.com/software/vectorscribe It offers tools to set fixed angles for drawing (Protractor) and to round edges (Dynamic Corners). EDIT: Protractor seems to have been removed from VS, but is now part of the free DirectPrefs astutegraphics.com/software/directprefs – AAGD Nov 6 '17 at 17:26
  • Very interesting plugin. Really powerful indeed. – Ideogram Nov 7 '17 at 8:04
  • Instead of using a pen tool use line tool – joojaa Nov 7 '17 at 18:42
  • Also its possible to make the os make shift or any other key sticky. – joojaa Nov 7 '17 at 18:56
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In Inkscape, you can define a grid with 45° (document setting), make the image partly transparent, enable snap to grid and thereby help yourself by manually performing the task, drawing over the shape to the nearest next grid point close to the shape:

enter image description here

I'm not aware of an Inkscape tool, being more into the automation of the task. Screenshot from german interface, I guess the location of the settings in the dialog is identical.

  • +1 for Inkscape and the 45º Grid. And indeed finding Zeeland ;-) – Ideogram Nov 7 '17 at 8:45
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You can alter the Constrain Angle in the Preferences > General to change the default angle artwork is created at.

enter image description here

  • Thanks for the trouble creating a little screencast! I'm afraid this doesn't help me. The setting you show doesn't affect the pencil tool. And it prevents the pen tool from drawing at 0º and 90º – Ideogram Nov 6 '17 at 18:27
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    If you just want pen tool paths to be at 45° you can hold down the Shift key when creating them. You can set the "shift angles" in Preferences > Smart Guides Then turn on Smart Guides in the View menu. And the Pencil tool is specifically designed to ignore all many snapping, guide, constrain, and grid settings in many instances to be "freeform" overall. – Scott Nov 6 '17 at 18:31
  • Indeed, the pen-tool-with-shift works . Apparently, what I want simply does not exist or I am not able to explain it clearly enough. – Ideogram Nov 6 '17 at 18:53
  • +1 for using Smart Guides. You might only need the Construction Guides active (s. Preferences), otherwise there's too much other snapping taking place. – AAGD Nov 6 '17 at 19:00

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