Christ Church lit by the last break in the cloud, shot from the hill.

The view is beautiful, of course: you are treated to a top-down view of the town, the pier, and the twin harbors in the distance. But the walk up that hill is grueling, and when you finally make it to the top, the view is punctuated by many deep breaths of fresh, crisp morning air. Although I had initially made the climb at first light, I was quickly reminded that the weather in Portland is often indifferent to my photography playbook. The morning was completely overcast, and so that evening I climbed again, hoping to catch some of that beautiful directional evening light; I could almost see those long cinematic shadows, but again the cloud cover prevailed. I took a few throwaway frames and walked the circuit of the hill back down into the town. I was on my way out of the town when the last of the evening light finally broke through the clouds. I noticed it striking the face of the old Christ Church as I walked along Harbor Street… So I climbed a third time. The light was brief; however, I did get a few good frames of the church and the streets below.

Port Antonio: Jamaica's Forgotten Capital of Paradise

I've started paying closer attention to the heritage sitting in plain sight around Portland. In Port Antonio alone: the Ken Wright Pier, Boundbrook Wharf, the crumbling Folly ruins, and a scatter of colonial churches — each one a chapter most visitors drive straight past.

Long before cruise ships found Ocho Rios, before the world-class hotel chains turned Negril and Montego Bay into household names, this town held the imagination of the entire world.

Before empire

The Taíno were here first, with villages along the rivers and sheltered bays. The Rio Grande gave fresh water; the forests gave timber, medicine and game; the sea gave the rest. They farmed cassava, maize and sweet potato, and traded across the Caribbean. Columbus claimed the island for Spain in 1494, and that idyllic era ended abruptly.

A harbour worth fighting for

Spanish Jamaica largely ignored the east — too wet, too steep, too forested. But the harbour was impossible to ignore: one of the deepest natural anchorages in the Caribbean. The name is thought to come from the San Antonio, a Spanish ship said to have sheltered here in the sixteenth century. Legend or record, it stuck.

After the English took Jamaica in 1655, the eastern parish became strategically awkward. The same terrain that discouraged settlement made perfect refuge — the Blue Mountains that guarded the towns like towering sentinels became the stronghold of the Windward Maroons, whose resistance shaped this island's history more than any governor did. Portland was carved out as a parish in 1723.

Timber, then coffee

The first British money here came out of the forest, not the field: mahogany, cedar and lignum vitae floated down the rivers to ships waiting in the harbour. Coffee arrived in the eighteenth century and immediately thrived in the cool highlands. Still, Port Antonio stayed small. Its transformation was yet to come.

The banana boom

In 1870, an American sea captain named Lorenzo Dow Baker sailed into Port Antonio and — rather than run home with an empty hold — filled it with bananas bought from local farmers. The fruit reached the US still good. The profit was absurd. Demand exploded.

Within a generation, steamships ran regular routes from this harbour to Boston, Philadelphia and New York. Thousands of acres across Portland were devoted to the lucrative banana farms. The railway reached Port Antonio in 1896 to move fruit from inland estates down to the wharf. For a stretch, this was one of the busiest banana ports on earth. This was Port Antonio's golden age.

Baker's venture grew into the Boston Fruit Company and eventually into the United Fruit Company — which would go on to reshape half of Central America.

Paradise, invented

The fruit boats came back carrying something nobody planned for: passengers.

Wealthy Americans stepped off the steamers into a landscape that looked staged. Rainforest running straight down into turquoise coves. Waterfalls out of dense bush. Rivers wandering toward empty beaches. Hoteliers moved fast. The Titchfield Hotel went up on Titchfield Hill in the 1890s — wide verandas, electric light, manicured gardens, a commanding view of the harbour — and it became one of the grandest houses in the Caribbean.

Port Antonio picked up a nickname: the Riviera of the Caribbean. A century before anyone said "eco-tourism," the landscape itself was the product. Nature was always the luxury.

Hollywood finds it

Errol Flynn's yacht sheltered here in 1946 and, like most people who wash up in this town, he never really left. He bought Navy Island and land out at Boston, invested in local business, and pulled Hollywood in behind him. He's also why you can raft the Rio Grande today — he watched farmers poling bananas downriver on bamboo and turned it into an afternoon for visitors.

The road not taken

When Jamaican tourism went west and all-inclusive, Port Antonio couldn't follow. Narrow coastal plain, steep mountains, nowhere to put a thousand rooms. The thing that capped its growth is the thing that saved it. Frenchman's Cove, Boston Bay, Reach Falls, Winnifred — still attached to the land around them.

Every river running out of the Blue Mountains has carried something: timber, coffee, bananas, travellers, stories. Port Antonio is a living archive, and the story is unfinished.

This is Port Antonio. This is my hometown.

One Frame

I crashed the Phantom 4 my big bro Nigel gifted me almost immediately, so elevation is my drone now. From the top of the hill, a long lens does most of what a drone does — the compression flattens the town into lines, grids and shapes you'd never notice standing in it.

A Location Note

Bonnie View Hill, Port Antonio. The road up from town is short and brutal — ten to fifteen minutes on foot, steep the whole way.

What you get: a top-down view over the town, the pier, and both harbours.

Best light is late afternoon into golden hour, when the sun crosses the harbour mouth rather than sitting behind it. But this is the wettest parish on the island. Assume cloud, plan two visits, treat clear light as a gift.

Reply and tell me which historical site deserves a short film — I read and answer every one.