Arrow keys move the silhouette, plus and minus resize it, Enter locks in your guess.
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Reference —
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Countries and US states as cut-outs, drawn on an equal-area projection so nothing near the poles is inflated. The ruler shows the reference’s span along its longer axis; make the other outline the right size beside it.
Why maps lie to you
The map on the wall is a Mercator projection, and it stretches everything far from the equator. Greenland looks the size of Africa; it is a fourteenth of it. Alaska looks bigger than Mexico; it is not. Size It Up Geography draws every outline on an equal-area projection centred on the place itself, so the shape you see is the shape that exists, and the only thing you have to get right is how big it is.
Every outline comes from Natural Earth, a public-domain map dataset, at a resolution of one to fifty million. Spans are measured on the sphere, not on the page.