A quiet little town that grew around its deep twin harbors, Port Antonio owes its origins as a tourist spot to actor Errol Flynn (1909–59). Having run aground here aboard his private yacht, Flynn took a liking to the Portland area, buying Navy Island just offshore and a hotel that used to stand on the Titchfield peninsula – the western tip of Port Antonio’s East harbor. By the 1950s, he was well-known for inviting a string of celebrities, including Bette Davis and Ginger Rogers to Jamaica to stay and go rafting on the Rio Grande.

Although little remains to be seen of the Flynn legacy today, the area does retain a sense of faded glamor, especially in the palatial resorts east of town. Port Antonio still has a certain shabby charm, with a few colonial-era buildings with typical overhanging verandas along its main street. There is a busy fruit and vegetable market and a grand old Georgian courthouse now being refurbished to its original glory.

Facing Navy Island is the new Port Antonio Marina, now known as the Errol Flynn Marina. The marina offers world-class facilities, including waterfront paths for promenading, manicured lawns, a slip of white-sand beach, and an upscale restaurant. Unfortunately, Navy Island is officially closed to visitors, though local fishermen still take people to its lovely beaches for a swim and to snorkel.