Cayman Cookout (January) is a food and wine festival attracting serious chefs — Eric Ripert has been a regular fixture for years. Events take place along Seven Mile Beach and include dinners, tastings, and cooking demonstrations. It's well-regarded and worth timing a visit around if food is your thing.
Pirates Week (November) is the biggest national festival of the year. It involves a mock pirate invasion of George Town harbour, street dances, costume parades, heritage days, and events across all three islands. It runs for about ten days and the atmosphere is genuinely festive. Don't expect a quiet trip if you visit in mid-November.
Cayman Carnival Batabano (May) is the islands' take on Caribbean carnival. Elaborate costumes, music trucks, and a parade through George Town. Smaller than the big Trinidad or Barbados carnivals but lively.
Kaibo Kitefest (February) is a family beach event on Grand Cayman, centred on kite flying, live music, and beach games. Relaxed and low-key.
Cayman JazzFest and the Cayman Islands International Storytelling Festival are organised by the Cayman National Cultural Foundation and reflect the islands' interest in preserving and promoting local culture alongside international performers.