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Traditionally, Cayman Pirates Week runs for eleven days in November. It is advisable to make arrangements in advance for ground transportation and harbor-side hotels because it is a popular event. Hotels fill up fast and rental cars may not be available during the festival if not reserved ahead of time. Many of the major events are free and most others are reasonably priced and family-friendly, making Pirates Week fun for the whole family.

Cayman’s Pirates Week Costumes, Contests and Musical Entertainment

Visitors to Grand Cayman during the Pirates Week festivities don pirate costumes, many similar to those made popular by the Pirates of the Caribbean movies. Men, women and children alike dress up to roam the streets and attend Pirate Week activities and competitions, including a best pirate costume competition.

Musical entertainment is provided for several harbor-side street dances throughout the week with dancing and partying into the night. Expect to find the best of the steel drum bands competing for the title of “best” at some point in the Pirate Week Schedule. The Pirates’ song fest is also a favorite.

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