You can keep doing that until you get to a single pixel. For simplicity here are some in between images and the final one boosted in size. Now that you have the final image you can get the color of it which you will see is a value of 40.
Now 40/255 = 0.1568 which is pretty close to the expected value. So take that value, multiply by whole map area and you have island area. Job done.
Here is a script to generate that process in ImageMagick.
Code:
convert start.png -filter box -resize 512x512 -sample 512x512 img512.png
convert img512.png -filter box -resize 256x256 -sample 512x512 img256.png
convert img256.png -filter box -resize 128x128 -sample 512x512 img128.png
convert img128.png -filter box -resize 64x64 -sample 512x512 img64.png
convert img64.png -filter box -resize 32x32 -sample 512x512 img32.png
convert img32.png -filter box -resize 16x16 -sample 512x512 img16.png
convert img16.png -filter box -resize 8x8 -sample 512x512 img8.png
convert img8.png -filter box -resize 4x4 -sample 512x512 img4.png
convert img4.png -filter box -resize 2x2 -sample 512x512 img2.png
convert img2.png -filter box -resize 1x1 -sample 512x512 img1.png