There are a number of festivals that happen on the Cayman Islands year-round. The annual Cayman Jazz Fest happens in late November or early December and features both local bands and international stars. The weekend after Ash Wednesday, the Cayman Carnival, Batabano, swings into gear. The streets swarm with people in colorful costumes as a parade of floats and Mas’ (masquerade) bands march through George Town. Then, there is the Pirates Week Festival, usually in November (just as tourist season is getting underway), which has a huge variety of events, including 5K and 10K runs, costume contest, fireworks, children’s fair, music concerts and dance competitions. Several of the days are also designated “Heritage Days” for each of the island’s main districts. Fishing aficionados will appreciate the month-long fishing tournament in June.

The Cayman Festival of Arts, or Cayfest, occurs on both Grand Cayman and Cayman Brac with both indoor and outdoor events. There are dance performances, art gallery exhibitions, crafts vendors, photography shows and cooking and singing competitions. The festival is sponsored by the Cayman National Cultural Foundation, which also puts on cultural and entertainment shows at its Harquail Theater, sponsors a national playwriting contest, and hosts the Gimistory Festival, which features local storytellers.