Alaska is about 16,279 times bigger than Anguilla.

Anguilla is approximately 91 sq km, while Alaska is approximately 1,481,348 sq km, making Alaska 1,627,755% larger than Anguilla. Meanwhile, the population of Anguilla is ~18,741 people (691,490 more people live in Alaska).
Tip: This to-scale comparison of Anguilla vs. Alaska uses the Mercator projection, which distorts the size of regions near the poles.