Kentucky is about 2.9 times smaller than Italy.

Italy is approximately 301,340 sq km, while Kentucky is approximately 102,896 sq km, making Kentucky 34.15% the size of Italy. Meanwhile, the population of Italy is ~61.1 million people (56.8 million fewer people live in Kentucky).
This to-scale comparison of Italy vs. Kentucky uses the Mercator projection, which distorts the size of regions near the poles. Learn more.

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