Anguilla is about 16,279 times smaller than Alaska.

Alaska is approximately 1,481,348 sq km, while Anguilla is approximately 91 sq km, making Anguilla 0.01% the size of Alaska. Meanwhile, the population of Alaska is ~710,231 people (691,490 fewer people live in Anguilla).
Tip: This to-scale comparison of Alaska vs. Anguilla uses the Mercator projection, which distorts the size of regions near the poles.