And now is an ideal time to plan a visit as December through April is the most popular time to visit the Cayman Islands. Temperatures during the “winter season” average a balmy 75 degrees with relatively low humidity. Plus you’ve got loads of festivals and events to align with your visit including the epicurean’s delight Cayman Cookout (January 16-20, 2019 at The Ritz-Carlton) to the Taste of Cayman happening January 26 at Camana Bay.