Kingston is charting a new course in cultural tourism with the introduction of Kingston Pirates Week, a transformative four-day festival scheduled from October 30 to November 2, 2025.

The launch for the weeks of events was held recently at the Jamaica Pegasus Hotel in New Kingston.

Powered by Jamaica Tourist Board, with the full endorsement of the Ministry of Tourism, the Tourism Enhancement Fund (TEF), and the Tourism Product Development Company Ltd (TPDCo), Kingston Pirates Week is positioned to become a flagship event on the Caribbean’s cultural calendar, attracting both domestic and international audiences.

According to Peter Shoucair, event consultant with expertise in both travel and marketing, Kingston Pirates Week was conceptualised following a comprehensive needs assessment of the city’s tourism sector.

“The…needs assessment that revealed an urgent call for destination-specific events that celebrate Jamaica’s unique history while offering high-yield visitor experiences. Port Royal’s maritime legacy is globally unmatched — yet under-leveraged. This festival transforms Kingston into a living stage for storytelling, cultural exchange, and economic impact,” he said.

At the heart of this unique initiative is the celebration of Kingston and Port Royal’s storied pirate past. Once known as the “richest and wickedest city on earth”, Port Royal’s heritage will be brought to life through a captivating schedule of activities, including costume-themed parties, interactive re-enactments, culinary showcases, guided tours of Fort Charles and the Giddy House, sound system tributes, and curated family experiences.

Festival highlights include the Riddims & Rum fete, Pirates & Wenches 4D all-inclusive, the Port Royal Pirates Festival, the Kingston City Run: Pirates Run Di City, and excursions such as the Halloween Harbour Cruise and treasure hunts to the cays off Port Royal. These experiences are intentionally crafted to provide economic uplift, showcase Jamaican creativity, and reposition Kingston as a destination of cultural and experiential significance.

The festival has garnered the strategic support of the award-winning Kingston City Run, a partnership that has evolved into one of the week’s marquee events. This year’s theme, ‘Pirates Run Di City’, will be integrated into the Kingston City Run 5K, adding a compelling narrative element to the popular charity race.

Nicola Madden-Greig, group director of marketing & sales at Courtleigh Hospitality Group, immediate past president of Caribbean Hotel & Tourism Association, and co-founder of Kingston City Run, noted: “Partnering with Kingston Pirates Week was a natural evolution for the Kingston City Run brand. ‘Pirates Run Di City’ is more than a theme, it’s a movement. It brings new energy to our long-standing tradition of merging health, charity, and urban exploration. We’re thrilled to add narrative depth and historical relevance to the experience, attracting a new demographic of cultural explorers, families, and fitness enthusiasts while benefiting key social causes.”

Visitors will be able to explore the recently developed Port Royal Museum, enjoy guided tours through iconic forts, and engage with the still-unfolding story of the Sunken City, which remains on UNESCO’s tentative list for World Heritage Site designation. By bridging the past with present-day innovation and entertainment, the festival is set to deliver a multifaceted impact on community engagement, economic development, and Jamaica’s international cultural reputation.

Joanne Paxton, executive producer, Kingston Pirates Week, presents Senator Delano Seiveright, minister of state in the Ministry of Tourism, a token of appreciation after his presentation at the recent launch of Kingston Pirates Week and Kingston City Run 2025.