Before a Hollywood star made it fashionable and before its banana ships brought the first tourists in Jamaica's history, the greenest and rainiest corner of the island already held centuries of history. The northeastern tip of Jamaica, where Port Antonio now stands, was inhabited in pre-Columbian times by the Taíno (Arawak), the island's original people. The region, mountainous and jungle-covered, with its mighty rivers like the Rio Grande coming down from the mountains, offered abundant resources to those who lived off fishing, hunting, gathering and farming. The thick jungles and mountains of the east would be, centuries later, a refuge for other persecuted peoples.
After the arrival of Columbus in 1494 and the Spanish colonization, this eastern area remained largely on the margins of the scant European settlement. The Spanish, who concentrated their presence in other parts of the island, nonetheless left their mark on the place names: the name 'Port Antonio' derives from Spanish names like Puerto Antón or Puerto de Antón, which with the later English rule were anglicized to the present form.
Throughout the Spanish period, the region remained underdeveloped and hard to reach, covered by the dense jungle of what are today the Blue and John Crow Mountains. That same inaccessibility, which delayed its colonization, would be key in the following century, when the area became a stronghold of the Maroons and, much later, an almost intact natural paradise that would win the hearts of the first tourists and the Hollywood stars.
After the English conquest of Jamaica in 1655, the mountains of the east of the island became a key setting of the resistance to slavery. In the inaccessible Blue and John Crow Mountains, the Maroons settled: communities of enslaved African people who had escaped from the plantations —some since the Spanish era— and who formed free settlements in the mountains, defending themselves with a deep knowledge of the jungle terrain.
The eastern Maroons, known as the Windward Maroons, waged prolonged guerrilla wars against the British during the 18th century (the so-called Maroon Wars). Their resistance was so effective that the English had to sign peace treaties with them, recognizing a degree of autonomy for their communities. The need to control and keep watch over these Maroons was one of the reasons the British Crown created the parish of Portland in 1723, establishing Port Antonio as the administrative and military center of the eastern region.
The authorities fortified Port Antonio (with installations like Fort George on the Titchfield peninsula) and tried to attract settlers to an area considered wild and dangerous. The presence of the Maroons, their culture and their legacy of freedom are a fundamental part of Portland's identity, and the mountains that protected them are today a UNESCO World Heritage Site, recognized both for their nature and for that history of resistance.
Port Antonio's great takeoff came in the late 19th century, and it had an unexpected protagonist: the banana. After the decline of sugar, the fertile, humid land of Portland proved ideal for growing bananas, and Port Antonio was transformed into one of the world's main banana-exporting ports. Companies like the United Fruit Company and figures like Captain Lorenzo Dow Baker drove a trade that connected Jamaica with the markets of the United States and Europe.
That banana boom brought more than wealth: it inaugurated tourism in Jamaica. The ships that came to load banana didn't want to return empty, so they began to bring passengers —tourists curious to see the exotic tropical island— and to house them the first hotels were built. The Titchfield Hotel, in Port Antonio, was one of the pioneers of Jamaican tourism. Thus, this eastern town can claim the title of the birthplace of tourism on the island, long before Montego Bay or Ocho Rios became famous.
From that banana era also comes a tradition that would become emblematic: the bamboo rafts used to transport banana down the Rio Grande would give rise, decades later, to tourist rafting. Port Antonio thus lived, between the banana and the first travelers, a moment of splendor that laid the foundations of its future as a destination.
If the banana put Port Antonio on the map, it was a Hollywood star who gave it its glamorous, romantic aura. In the mid-20th century, the actor Errol Flynn —famous for his roles as an adventurer and heartthrob— arrived in the area, according to legend after a shipwreck or a chance stopover, and was completely captivated by its beauty. 'More beautiful than any woman I have ever known', he is said to have said of Jamaica.
Flynn settled in the area, bought properties —including Navy Island, off Port Antonio— and drew, with his presence, other Hollywood stars, millionaires and celebrities, who began to frequent Portland and to build villas hidden among the vegetation. Port Antonio thus became an elite destination, exclusive and bohemian, very different from the mass tourism that would later develop in other parts of the island. That elegant, leisurely air can still be felt today.
Flynn also left a lasting mark on tourist activity: fascinated by the bamboo rafts of the Rio Grande, he helped to popularize the races and rafting as an attraction, giving rise to Jamaica's tourist rafting. The actor's memory remains present in the area, in place names, anecdotes and the charm of villas and hotels that inherited that spirit. The Errol Flynn era defined the identity of Port Antonio as the sophisticated and secret Jamaica.
The natural beauty of Port Antonio and its surroundings did not go unnoticed by film, which helped make its landscapes world-famous. The most celebrated example is the Blue Lagoon, that pool of a hypnotic blue where the sea mixes with freshwater springs, surrounded by jungle. The lagoon gave its name and setting to the film 'The Blue Lagoon' (1980), starring Brooke Shields, which carried the image of this Jamaican corner around the planet.
But Portland's natural richness goes far beyond a lagoon. The region is home to dreamlike waterfalls like Reach Falls and Somerset Falls, unspoiled beaches where the jungle meets the sea (Frenchman's Cove, Winnifred Beach, San San), and the mighty Rio Grande that comes down from the mountains. All of it in a setting of lush rainforest, fed by the abundant rains that make this one of the greenest areas of Jamaica.
Behind Port Antonio rise the Blue and John Crow Mountains, declared a UNESCO World Heritage Site in 2015 —the first and only Jamaican site on the list— for their exceptional natural value (biodiversity, endemic species) and cultural value (the refuge of the Maroons). This combination of intact nature, history of resistance and cinematic glamour makes Port Antonio a unique destination, the most authentic, wild and romantic face of Jamaica.