Backed by a team of athletes, models, and writers, a hiker traverses volcanic trails on the remote island of St Helena, collecting stamps from cliff-tops before confronting the deep, dark void of the Atlantic Ocean and the monsters that dwell within.
Janneke shrieked and leapt onto a jagged boulder, her eyes locked on the dark volcanic rock face. “I don’t like crabs!” she said, shuddering as she balanced above the swirling tide. Flashes of crimson—the eastern Atlantic Sally lightfoot crabs—scuttled across the black basalt, vanishing into shadowy overhangs.
Our group of five had just descended an almost sheer drop with the help of a thick mooring rope, anchored to assist hikers on the rugged Lot’s Wife’s Pools trail. These natural rock pools, protected from the surging Atlantic on St Helena’s wild windward side, marked our rest stop and turnaround point. But first, we had to get past the crabs.
St Helena, a British Overseas Territory, is one of the most remote inhabited islands on Earth. It sits in the middle of the Atlantic, 1,210 nautical miles west of Angola and 2,500 nautical miles east of Brazil. For centuries, the only way to reach it was by sea. In more recent history, it was a six-day voyage from Cape Town aboard the RMS St Helena. However, the island’s airport opened in 2017 and travel time was drastically reduced to six hours from Johannesburg and five from Cape Town.
The airport is a marvel of engineering, carved from volcanic rock on a windswept plateau 1,000 feet above the sea. Stepping outside, I felt like I’d landed on Mars—barren, rugged, and austere. It was hard to imagine the lush peaks, cloud forests, and hidden valleys waiting beyond.
Crossing the island from east to west in about 20 minutes, we stopped to admire the Heart-Shaped Waterfall before descending into Jamestown, the island’s capital. The town is a narrow strip wedged between two near-vertical cliffs. Its pastel buildings and stone fortifications line the main street that passes through an arch to the harbour. Parts of it reminded me of an older, tattier version of Simon’s Town, near Cape Town, which has similar echoes of British naval history.
I was exploring the island with Dutch trail runner and sports model Janneke Scherpernhuyzen, triathlete and editor of Run magazine, Paul Ingpen, travel writer Iga Motylska, and Italian aviation writer Matteo Legnani. One of our guides for the week was the affable Tom Wortley who runs Rockmount Walking Tours. Originally from the UK, Tom moved to the island in his early twenties, following his wife back to her hometown. “I was lucky to snag her—I have a huge nose and my ears are like satellite dishes,” he joked, keeping us entertained with his self-deprecating humour and quirky observations about life on the island.
Tom loves the mountains and was eager to show us St Helena’s trails. The island has 21 official “Post Box Walks”—routes that traverse a variety of trails each ending with a post box. Inside there’s a visitors book and a unique ink-stamp. One of the most striking of these is the Blue Point Trail. Starting just beyond Thompson’s Wood, the path winds through arid hills, past spiky prickly pear bushes, and wind-stunted shrubs, before opening onto a dramatic cliff-top view.
Part of the walk was sheltered, yet the wind whipped my hair into a tornado of ribbon-like stands at the post box. It felt exhilarating to be standing at Blue Point with views of Speery Island and the Atlantic. We stamped the book and left a comment before leaving.
“This is the one the kids do,” Tom laughed, implying that if we struggled on this hike, we wouldn’t manage the more challenging trails. It was an easy yet awe-inspiring walk that took about 40 minutes each way. As we retraced our steps, the light fell on the towering spire of Lot’s Wife below us, dramatically highlighting the pinnacle. A few days later, we would be back, walking along the coastline beneath the rocky outcrops of Lot and Lot’s Wife, looking up at the razor-sharp peaks of the Gates of Chaos.
Despite her dislike of crabs, Janneke is adventurous. It didn’t take much convincing for her to follow me across the basalt, into an adjacent bay. The beach was a mix of smooth pebbles and dark sand that made a crunching sound underfoot. “It’s usually a lot calmer,” said Tom as waves churned over the natural rock barrier separating the pools from the open ocean. Paul and Iga waded in. “It’s always the South Africans,” Tom chuckled. “You never hesitate.”
After slipping on his goggles, Paul, a strong ocean swimmer, soon reached the outer edge where the surging Atlantic cascaded into the pools. He ducked under the water, and resurfaced seconds later, grinning. “It’s incredible! Loads of fish—blenny, wrasse, and more!” Before we could respond, he disappeared beneath the surface again.
I didn’t swim that day; however, I’d spent plenty of time in St Helena’s water. The ocean here is surprisingly warm—not icy like the Atlantic, which I’m accustomed to much further south. St Helena sits in the subtropics, and its leeward side offers some of the best diving and snorkelling in the world. The visibility is remarkable and can reach up to 40 metres. You’ll find shipwrecks, caves, and reefs teeming with life, including the endemic St Helena butterflyfish. Spinner dolphins leap alongside boats, and whale sharks aggregate here between December and April.
I didn’t want to leave Lot’s Wife Pools. I felt immensely privileged to be in this cove where few souls have set foot. However, we had to get back before nightfall, which would eventually plunge the Gates of Chaos into blackness so deep it would mirror the inside of Leviathan’s belly.
The path meandered through a geologist’s dream world. Beyond the curious forms carved by the elements, the layers of coloured rock told a story that I couldn’t decode. There was one last obstacle—passing back through a colony of masked boobies nesting along the path. Tom had a walking stick and on our way, had warned us that they occasionally nest right in the middle of a path. “Just make sure that the stick is closest to the beak and not your legs. They have a nasty bite.”
As we neared the final stretch before descending to Sandy Bay, we came across the boobies. We moved between them slowly, trying not to create a disturbance. I felt like a nature documentary photographer and imagined Sir David Attenborough’s voice narrating: “Perched on St Helena Island’s windswept ledges, a remarkable seabird—the masked booby — makes its home. These creatures, with their striking black-and-white plumage and piercing yellow eyes, are here to prepare for the next generation on one of the planet’s most remote outposts.”
Some of the boobies flapped their wings or cried out in warning as we passed by. One adult sat almost immobile on a large chick’s head, its body protruding awkwardly from under the protective parent. After marvelling at the scene for a while we started our last descent.
The late afternoon sun cast long shadows over the volcanic slopes when we reached Sandy Bay, and our vehicle. I’d arrived on this fortress of rock with feelings of reservation and yet the dramatic mountains, bucolic interior, fern-lined roads, quaint towns, and vibrant ocean offered endless adventures, making St Helena unforgettable. But perhaps what lingers most is the kindness of the people who welcome you as if you’ve always belonged on this extraordinary rock in the Atlantic.
