Anguilla has comfortable temperature and humidity levels year round. The best weather in Anguilla is probably April-May and October-November. Winter temperature is usually around 80 degrees. Summer temperatures vary from 80-85 degrees with humidity around 60-75%. In Anguilla, the average high June temperature of 86F is only 4 degrees above December's 82F. (Source: CN Traveller) Anguilla averages about 40 inches of rain per year, which is semi-arid. Most of it falls in sudden tropical downpours or in nightly showers. Humidity rises to 90% in the middle of a tropical downpour but is steady around 60% to 68% Hurricane season starts in June and runs until November. Statistically, the vast majority of Caribbean storms occur during the 2-week period centered around September 10th. That is why many hotels close for the month of September. Water Temperture - during August-October water temps averaging 82F-84F