There are all of two seasons that you need to know about the weather of the Grand Cayman- winter and summer. Come to think of it, there’s no offseason for visiting the Cayman Islands. The popular season is the winter when the worst of the rains and thunderstorms have passed. People throng the Islands by the dozen and prices are at an all-time high; make your reservations in advance to avoid the last minute rush and rates. The summer of the Grand Cayman is inclusive of the monsoon and the hurricane season lasts from June to November.