The British government originally gave the island to Governor Thomas Lynch of Jamaica as a reward for services to the Crown. It was known for a time as Lynch's Island. The Royal Navy eventually took control, installing a gun battery on the eastern end and lending the island the name it carries today. Captain William Bligh, whose name would later become synonymous with the mutiny on HMS Bounty, used the shallow waters facing the mainland as a careening station, a place where ships were turned on their sides so crews could scrape barnacles from the hull and perform maintenance. For the Navy, the island was functional, not glamorous: a useful anchorage in the sheltered harbor of Port Antonio, nothing more.

When Flynn purchased Navy Island in the mid-twentieth century, he transformed it from a forgotten naval station into a legend. The royal palms he planted still stand today. His caretaker, whom locals knew simply as 'the Governor,' lived in the only permanent structure on the island. Flynn himself preferred the deck of the Zaca, a 118-foot schooner he had purchased after the war. He sailed it to Port Antonio and made the island his base for deep-sea fishing, drinking, and entertaining guests in a setting that required no walls. Flynn's Jamaica years were his late period, after Hollywood had moved on from the adventure films that made him famous. The island suited this chapter of his life: beautiful, remote, and unburdened by expectation.

After Flynn's era, a Los Angeles land developer named Len Koutnik purchased Navy Island and envisioned an exclusive resort called Jamaica Islandia. The Jamaican government pressed him to begin construction, forcing him to scale back his plans for ultra-luxurious accommodations. Harry and his wife Eiler, a California couple, built the first house. Joseph and Gertrude Casey from Rhode Island joined Koutnik to construct a hotel with surrounding villas, but Koutnik ran out of money and the Caseys assumed control. Joseph Casey died before the project was finished. Gertrude offered the Eilers a lease on the entire island to complete construction and operate what became Jamaica's only private island resort: the Admiralty Club.

The Admiralty Club lasted five years before it ended in a scene Flynn himself might have scripted. The Eilers fired an employee for stealing funds. The dismissed worker rallied the resort staff into open rebellion. The employees seized control of the island and commandeered the two boats used to ferry guests from the mainland, stranding the Eilers on their own property. The couple was held until they paid termination wages to the rebellious staff. Once free, the Eilers left Navy Island immediately and never returned. Gertrude Casey resumed oversight, but the island's reputation as a viable investment had been shattered. Legal stipulations compounded the problem: anyone visiting the island had to be allowed access to its amenities as a guest, and a public beach was required among the rental villas. These conditions made Navy Island unattractive to the upscale developers who were the only investors likely to afford its remoteness.

In time, the Jamaican government bought out every remaining land title and closed Navy Island to development. It remains uninhabited today, a green hump of jungle visible from Port Antonio's waterfront, its royal palms still rising above the canopy as the only lasting monument to any of the grand plans that have been laid for it. From a colonial governor's private holding to a naval outpost, from a movie star's playground to a failed resort, Navy Island has cycled through ambitions for over three centuries without any of them taking permanent hold. The pattern suggests that the island itself is the constant, indifferent to whatever human purpose is projected onto its 64 acres, content to grow back over whatever is built and wait for the next dreamer to arrive.