Best Times to Visit Anguilla
The best time to visit Anguilla is between May and August, that's when you stand the best chance of getting a good package deal and also avoiding the worst of the hurricane season. Hotel prices are fabulous from September to November, but selection is sparse -- many properties close down. The most expensive time to visit (and also the most perfect weather) would be the early winter until spring.
Anguilla's peak season kicks off in mid December and lasts until mid April; the flight deals diminish and the hotel rates skyrocket. But the weather vouches for the influx of tourists with infrequent rain and average high temperatures in the 80s.
The weather is a tad more humid at this time, and you'll see the rainfall pick up, especially with the start of hurricane season. But this is a prime time for spendthrifts: Hotel rates can drop as much as 50 percent.
You'll get an outstanding room deal in the fall; that is, if you can find a hotel that's still open for business. Many of them close down for September to October (as do the choicest restaurants), so you might want to hold off until November if you're looking to travel in this season. The average temperature is a pleasant 80 degrees Fahrenheit, but Anguilla is in the heavy throes of hurricane season and you can expect a good clip of rain.