Cayman Islands (Grand Cayman) in May

December through April delivers perfect weather — mid-80s, low humidity, and almost no rain. This is peak season, so expect resort rates to double and restaurants to require reservations weeks in advance. May and November offer the sweet spot: great weather with shoulder season prices. You'll save 30-40% on hotels, and the crowds thin out significantly. The water stays warm year-round (82-84°F), so diving and snorkeling remain excellent. Here's the truth about hurricane season (June through October): yes, storms can hit, but Grand Cayman sits south of the main hurricane belt. Most storms pass north of the island. That said, when one does hit, it can shut down the island for days. Travel insurance becomes non-negotiable during these months. The rainiest months are September and October, but tropical showers usually last 20-30 minutes before the sun comes back out. Pack a light rain jacket and don't let weather apps scare you off.