New York is about 1,344 times bigger than Anguilla.

Anguilla is approximately 91 sq km, while New York is approximately 122,283 sq km, making New York 134,277% larger than Anguilla. Meanwhile, the population of Anguilla is ~18,741 people (19.4 million more people live in New York).
Tip: This to-scale comparison of Anguilla vs. New York uses the Mercator projection, which distorts the size of regions near the poles.