Answers from Our Experts (1)
It's hard to find a bad time of year to soak up the Caribbean sun, but some months are better than others when it comes to the Cayman Islands. The most popular time for visitors is during the winter, which also happens to be the dry season. Hotels get booked months in advance for the winter holidays because — let's be honest — everyone wants to come back to the chilly north with glowing tans. The dry season (which also happens to be the high season) is between November and April, and if you plan your trip during this time, you'll also be treated to plenty of conch as it's conch season as well.
Technically May through October is considered the rainy season, with May and October being the rainiest of them all; but I was just there at the beginning of May and the sun was shining the entire time. I will say, however, that the humidity makes things a lot hotter, but it's nothing a dip in the turquoise water can't solve. Once spring breakers clear out, the island is rather quiet — a few cruise ships here and there. Hurricane season comes during the summer, but the Caymans are usually spared (with the exception of a few hard hitting storms every few years).