Saint Helena: A Gem in the South Atlantic
I arrived early Saturday morning (22 November 2025) at Johannesburg O.R. Tambo international airport 🛫 having zero idea of what kind of trip this was going to be. It was a pretty big risk to pay so much and commit to a week with 11 strangers on my first international hike.
But that’s the nature of adventure.. stepping into the unknown to see what lies on the other side. I did zero research about the island but knew from experience that low expectations usually = a fun trip. Those adventures have always been my favourite. Sometimes all your plans go wrong and you still end up having a great time laughing your ass off 😂 with good friends.
Turns out our leader, Willie, was pretty experienced himself and had a real knack for researching and planning great trips to unusual destinations.
After refuelling in Walvis Bay, we landed with a bit of a bump on a runway which quite literally drops of a sheer cliff. Spectacular and a little nerve-wrecking! Jamestown, the capital of Saint Helena, fits snuggly in a deep valley and looks quite unusual for anyone coming from the big smoke.
Our focus for this trip was on the landscapes. And while there are obviously other things to do on the island, exploring by foot was always top of our priorities.
Post Box Hiking
There are 21 official trails on Saint Helena with post boxes at the end of each hike.. a tradition that has been running for almost 25 years. The idea came from Dartmoor, England where trail builders created hidden boxes 📬 for hikers to exchange postcards or stamps.
Post has always played an important role on the island. Saint Helena is a British Oversees Territory 🇸🇭 and for centuries, the only communication with the outside world was by Royal Mail Ship.
Locals and even some visitors carry a Post Box Walk Passport and there’s a certain respect that comes with completing all 21 walks.
The Sugarloaf Trail
We hit the trail from the guesthouse in Jamestown up above The Wharf and along the coast passing several battery’s on the way to Sugarloaf hill.
The English were paranoid about a high profile Frenchman that you’ve no doubt heard about – none other than one Napolean Bonaparte who was exiled to Saint Helena until his death in 1821.
As we traversed we came across several towers, ammunition banks and rusted cannons 💣.. remnants of the British guard.
The rock here has that volcanic, dusty feel 🌋 and I briefly thought that if the rest of the trip was going to be like this, it was going to be a bit disappointing. Boy was I wrong. The diversity on St Helena is something to behold and makes you appreciate every day’s hike.
Over the course of the next week we travelled through grassland, over boulders, through fields, and even small patches of forest. The entire island is only 16km (±10mi) long but there’s plenty to explore.
A Walk Through History
The trip also held historical significance for some of the Afrikaans hikers. Between 1900 and 1902 some 6000 Boer prisoners-of-war were exiled here. On day 3 we passed by the camp site and later paid our respects at a graveyard.
Willie gave the English-speakers a bit of a hard time as we traced the footsteps of prisoners past. It was all a bit of fun of course and the team spirit of a diverse group of 12 South Africans was always high. I jokingly explained that I have English, Afrikaans, and Italian blood in me so the heritage lines are way too blurred these days.
Island life is slow and measured and Saints are a friendly bunch. They certainly have their fair share of problems but there’s something beautiful about a simple life spent in the company of good people.. away from the chaos of the world.
Perhaps that’s why Jonathan, the oldest known living animal (tortoise), is still keeping it real on Saint Helena. He’s estimated to be 193 years old and is still wandering the grounds of Plantation house – seen below.
There’s way too many memories to recount them all here, but I loved every minute of this trip. If you like hiking and you love adventure, I think it’s fair to say that Saint Helena should be on your bucket list.