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Drawing polygons with holes have haunted me for a while and recently I had to do it in Python with PIL. Googling the subject gives you a hint. This code: import os import Image import aggdraw draw = aggdraw.Draw('RGB', (100, 100), 'white') path = aggdraw.Path() path.moveto(10, 10) path.lineto(10,60,60,60) path.lineto(60,10) path.lineto(10,10) path.moveto(20,20) path.lineto(40,20) path.lineto(40,40) path.lineto(20,40) path.lineto(20,20) pen = aggdraw.Brush("black") draw.path((25, 25), path, pen, None) img = Image.fromstring('RGB', (100, 100), draw.tostring()) p = os.