The Glamour Capital: Port Antonio’s Flynn Era
The Transition to the Celebrity Era (1940s–1959)
If bananas and steamships provided the hardware for Port Antonio, the mid-20th century provided the charisma. During the 1940s and 1950s, the town transitioned into a "glamour capital," anchored by the presence of Errol Flynn. This era created a lasting cultural afterimage—a vision of Port Antonio as a discrete hideaway where the global elite could exist outside the machinery of mass tourism.
The celebrity era was centered around Navy Island and a series of high-profile social circles. Flynn, alongside his wife Patrice Wymore, became the figurehead of a postwar mythology. The Jamaican press of the time documented frequent parties that hosted Hollywood royalty, including Bette Davis and David Niven.
Port Antonio's branding often blurs the line between documented history and local legend. The popular story that Errol Flynn "won" Navy Island in a high-stakes card game is a staple of local folklore and travel media, yet it remains uncorroborated by official property records.
This period of elite nightlife had a profound impact on local cultural production. The entertainment for these private parties often featured local musicians, pulling traditional forms into a new, global orbit.
The mento tradition—Jamaica’s original folk music—found a unique platform during this era. The Jolly Boys, perhaps Port Antonio’s most famous musical export, emerged from a 1940s group that performed at Flynn’s parties. This illustrates how elite social life provided a paid network for local artists, effectively preserving and packaging "authentic" Jamaican sounds for an international audience.
The celebrity-centered phase began to lose its momentum at the end of the 1950s. The decline was accelerated by both individual and environmental factors. Hurricane Charlie in 1951 had already dealt a severe blow to the town’s infrastructure and agricultural backbone. The epoch finally closed its principal chapter in 1959 with the death of Errol Flynn, leaving Port Antonio to settle into its modern identity: a quiet, rain-green time capsule of a grander, more volatile past.