Hiking St Helena Island; Footpaths, strolls and Post Box walks
Last updated on May 18th, 2026 at 04:21 am
Walking in Saint Helena is one of the best ways to experience the island’s incredible natural beauty. It has everything from gentle countryside strolls in lush green valleys, to crossings of volcanic moon-like landscapes, climbs to cloud forest peaks, and to challenging coastal and mountain hikes with dramatic cliffs and stunning ocean views. Among the island’s most popular walks are the famous “Postbox Walks,” where you hike to hidden postboxes scattered across the island and stamp your progress along the way. whichever walk you chose, every walk on St Helena really is a unique adventure surrounded by nature!
So if you’re heading to the island and fancy a bit of hiking, this post will tell you what Saint Helena has to offer!
First a few important links to use when you plan your trip. Yes, they are affiliate links, but I use them all for my travels, and if you do too it will help me keep producing this content. Cheers!
Planning for your trip
Language / Money – English / St Helena Pound (equivalent of the UK pound)
Flights – use skyscanner or booking.com to find and book your flight – I often find the same flight for a lot cheaper than booking direct with the airline!
Insurance – Use EKTA or SafetyWing. TBH I usually use EKTA – they accept any nationality, any age and its ok if you are already traveling – which is perfect for me!
Accommodation – use booking.com or for a hostel – Hostelworld. I use both.
Internet – buy a yesim eSim or Airalo before you go. I use both depending on where I am going.
Buses, trains, ferries – 12Go is always my first option for buses, ferries and trains
Car rental – use DiscoverCars – they are my ‘go-to’ car rental site
Hiking – I use AllTrails for online and offline hiking trails – it means you know exactly where you are on the trail and makes getting lost a lot harder!!
Tours and Activities – book with Viator, GetYourGuide, or Eatwith.
Thanks so much if you use one of these links – it costs you nothing but helps me keep writing!
Walking in Jamestown
1. Walk the town
Start by getting to know a little about the island and its history simply by walking around the Georgian buildings, complete with decorative cornices, sash windows, and wrought-iron balconies, in Jamestown. The tourist office has great maps with points of interest.
Not to be missed, apart from walking up Main Street, are the Archway as you enter town from the port, the adjoining Castle and its gardens (17th century), the Grand Parade, the Governor’s Residence, and the St James church with its bell tower.
A tour to get an insight to the intriguing history of the island and the buildings is not a bad idea! Finish at the museum, ready to start the next walk up Jacob’s Ladder.
2. Jacob’s Ladder
No visit to St Helena is complete without completing the 699 steps up Jacob’s Ladder to Ladder Hill Fort at the top. Not a great walk if you have vertigo, but still not to be missed.
The good news is that after conquering the near vertical staircase, you can take the easy way down – slide down the rails! An added bonus, apart from the views, are the tropic birds that you will see in the area.
The time record to go up is 5 minutes 4.19 seconds, set by Sam Collins on 29th January 2024, beating the last record set in 2013! Allow more like 10-15 minutes to get up unless you are super fit.
3. The Wharf
Grab a coffee from the St Helena Coffee Shop and stroll along the wharf to the Landing Steps. You quite often see dolphins and the comings and goings along the waterfront are always interesting.
Sites for a Stroll
1. Sandy Bay
Down the steep winding Sandy Bay Road you get to the beach – its about a 300m walk from where a non-4wd car would park. Wander along the black sand beach and you will see a number of canons and one side of old fortifications built during Napoleon’s exile. This is also the starting point for Lots Wife’s Ponds Walk – one of the Postbox Walks.
2. High Knoll Fort
Yes – its an old fort and there’s not really that much to see in the way of forts, but the views are absolutely worth taking a bit of time to stroll around here.
3. The Boer POW cemetery
At Knollcombes there is a hillside cemetery close to the church, with numbered graves – no names! These are graves of the Boer POW;’s that died here during their internment from 1900-1902. The names of those who dies are marked on two big obelisks at the bottom of the hill. Its a peaceful place for a stroll and contemplation.
4. Millennium Forest walk
This is a major restoration project planting endemic species like ebony, but particularly the exceptionally rare ‘Bastard Gumwood’ trees that used to full the Great Wood – which was destroyed by early settlers cutting trees for wood. It is an ambitious and incredible project covering 250 hectares – you can help by planting a tree.
Short Walks and Footpaths
The following walks all take approximately one hour. Not all walks are listed here but the ones that had more appeal (to me)!
1. The Longwood Boundary Walk
Starting at the Millennium Forest, the Longwood Boundary walk takes you along the remains of the Great Wood Wall. The wall was started in 1723 and meant to enclose the remains of the great wood to protect the trees – it was already a major conservation issue back then. It was started but never finished (unfortunately). Great views of Flagstaff and the Barn on the way.
2. Samson’s and Saddle Battery
A ‘great views’ walk along the rugged cliff above Jamestown to old battery sites -complete with canons of course.
3. Plantation House Walks
If you come to St Helena, the other must do thing is to see the oldest living land creature – Jonathon the tortoise who lives at Plantation House. there are also three short walks in the area you can do while visiting Jonathan – the starting point is the carpark by the gate to view the tortoises.
- Walk around the Ladies’ Bath (a spring used by the ladies for bathing in days gone by) and the Butcher Graves (graves of an enslaved husband and wife – he being a butcher as you will see). Continue the loop back to the carpark. (1km)
- Much the same, but walk along the road, behind Plantation House, then join the path where you can backtrack a little to the Ladies’ Bath and then onto the Butcher Graves and back to the carpark. (1.3km)
- A longer route continues on from the Butcher Graves to the Big Rock viewpoint and then back to Plantation House. Go via the Ladies’ Bath to the graves first. (3km)
Hiking St Helena’s 21 Post Box Walks
Hiking in St Helena really centers around the Post Box Walks. These are ‘the’ walks to do and the big drawcard for hikers to St Helena. They are scattered across the whole island and cover all terrains and landscapes across the island. They are not to be missed – well at least some of them.
Post Box Walks are called this because at the end (usually) there is a post box type arrangement with an ink stamp you can collect. Each stamp is different and names the walk you have just done.
Get a map and booklet on the walks from the Tourism Office before you go walking and stamp them off as you go – its a fun souvenir from your trip!
Without further ado – this is a brief summary of what you will find. (Note: I walked without a guide in all cases but you can take tours on these walks and no doubt learn a lot about the island as you go.)
1. Blue Point (1.5 hours)
I loved this walk – such contrasting landscapes starting with the multi-coloured earth around you to the black sand of Sandy Bay below. It helped it was a misty kind of day when I did this as it somehow enhanced the scenery over the cliffs to the sea, islands and rocks below. A stunning walk is all I have to say.
2. Cox’s Battery ( 1 hour)
This path follows the remains of the Great Wood Wall – Boundary Wall. You see the new airport in its barren landscape – it always seems very barren to me there for some reason – as well as fabulous views of more rocks – Turk’s Cap, The Barn, King and Queen Rocks and Prosperous Bay Beach. As you go to Turk’s Cap valley you pass through old fortifications. there are so many on this island!! Its not steep but there are steep drop-offs on each side of the ridge you walk on to get to the battery.
3. Manati Bay (4 hours)
One I didn’t get to do. From what I was told it starts in farmland and follows a donkey track through guava and banana trees down to the coast. Apparently there are no steep climbs which makes it a good option really!
4. Diana’s Peak (2.5 hours)
My top favourite! I have nothing bad to say about it. Mainly because it was an easy but great ridgeline trail across three peaks, right in the cloud forest area with great views across the island. And to top it off I found the red blushing snail there – I was sooo excited by that. There are other endemic species here – lots of signs to read about them. Don’t miss it whatever you do.
5. Sugar Loaf (4.5 hours)
A harder one again! You can walk to the Sugar Loaf peak from either Rupert’s Valley or Deadwood Plain. From Deadwood Plain you start on the Flagstaff track, then weave down through gorse bushes along barren ridges above sea cliffs to get to the Sugarloaf itself. From Rupert’s you also get a lot of coastal views as well as Munden’s fortifications and Bank’s battery (which I didn’t see.)
6. Great Stone Top (3.5 hours)
This is a great hike through the dry coastal areas from Bellstone (a large rock which rings like a bell). You walk past past Little Stone Top and above Shark’s Valley with dramatic views over the cliffs at the end. It’s not too tough, and you should see the red billed tropic birds as you go as a bonus. It would be a good place for birdwatchers to watch seabirds.
7. Lemon Valley (3.5 hours)
I didn’t do this walk which follows a green valley down to the coast. It looks like a very cool old wall at the end as well as old quarantine buildings to explore. It is good for swimming and snorkeling (no currents) so I probably should have gone there!!
8. Peak Dale (2 hours)
This is another easy walk that weaves through flax, farmland, and woodland with pleasant views across Sandy Bay. The main reason for this walk, in my mind, is to see the last remaining ancient stand of endemic gum wood on the island. How special! This is a key plant they have been planting in the Millennium Forest.
9. The Heart Shaped Waterfall (1.5 hours)
It definitely is a heart shaped piece of rockery when looking from the road, but there is only water in the waterfall when its been raining hard. I missed out on that but really enjoyed the little walk. There were lots of terns swooping around when I go to the (waterless) falls. A nice walk through through wild mango and island scrubland to get there.
10. Lot’s Wife’s Ponds (3.5 hours)
The other big favorite – mainly because you get to swim in fantastic rock pools at the end of it! Start at Sandy Bay and zig zag up – with little stone cairns here and there on the path. At the highest point on the path are great views of Gorilla’s Head and Asses Ears. (They look like their names.) There are some quite steep drop offs on the path. The post box is above the ponds. To get to the pond you need to go down a small cliff – with the help of a rope. Its worth it!!
11. Powell’s Valley (3.5 hours)
I didn’t do this walk but its meant to be very tough! I don’t have much info but they say the walk goes from farmland at Level wood and Sandy Bay, past two military batteries, down to the stark coastal valley. sorry for the lack of info there!
12. Prosperous Bay (4 hours)
This is the only walk with flowing waterfalls! It also has wow views – once again (toward the Barn and airport and Diana’s Peak)! Walk down the valley, past the waterfalls, to a beach with rock pools to poke around in and more military remnants!
13. High Hill (2 hours)
This is quite a short and easy walk through nice woods to the top of High Hill – which apparently has spectacular views…… when its not raining!! Its a nice walk through the woods though and I am sure the view is normally great.
14. Lot (3.5 hours)
The main point of this walk, apart from the views of course, is to see Lot – a great big rock that is a remnant from volcanic times. You start down the Fairyland track with plenty of thorn trees (so it seems badly named). It gets drier and more difficult as you get toward Lot where you get the views out over Sandy Bay.
15. Sharks Valley (4.5 hours)
Again, I missed this one but it is apparently quite impressive. With deep valley is a great walk, however more difficult than most. Starting from Level wood, it is one of the only valleys with a constant flowing stream on the island, ending at the rocky valley mouth that opens to the sea, on route you will see banana trees and sightings of wild mangoes.
16. Sandy Bay Barn (3 hours)
Another reasonably easy walk with more bright coloured earth and more views, beautiful of course, across Sandy Bay to Lot and Lots wife. It starts on green farmland and the contrast is great between the two areas, and follows the Sandy Bay ‘amphitheatre’ and its rocky layers, with its great panoramic sea views! This one is really good value for the effort.
17. South West Point (3 hours)
A pretty easy walk (yah) mostly through pretty farmland. You get great views – especially over Manati Bay and Sperry Island with little effort – a real win-win! You might also see the wirebird on the way if you are lucky like us! At the postbox itself, the land has changed from green fields to bare red, pink and ochre earth which is just as beautiful. A great walk and up in the top list!
18. The Barn
A tough one from all accounts – I didn’t do it unfortunately! It starts at Deadwood Plain, then goes through some interesting geology to the top of a huge volcanic bluff – the Barn. The post box is at the top of the Barn – which is flat, after walking on very steep slopes and ridgelines to get there. There are fantastic, even extreme, sea and coastal views from the top from what I have seen.
19. Flagstaff (1.5 hours)
This is an easy to follow track, although not my favourite. The real bonus is that you are likely to see the endemic wirebird here. Fingers crossed – I didn’t but think I was just unlucky – or too noisy as there was a group of us! You start from Deadwood and walk past where one of the Boer POW camps were on Deadwood Plain (nothing to see but interesting to contemplate). Then walk through scrub and a small forest to a viewpoint. Not as dramatic as other walks, but good to do at the same time as Sugar Loaf.
20. Thompson’s Valley (4 hours)
This is a varied walk – through fields with big rocks scattered across, then forests to a plain, coastal rock hilltops, and finally the exposed coast where there is the remnants of a tower and further on another battery complete with canon. Its steep in places, especially the last bit down to the rocky beach at the end of the track.
21. High Peak (1.5 hours)
I thought this whole area was so lovely and enjoyed this walk to great views. I always think of the flowers when I think of this walk! Once again, the views from the top were fabulous. (See the feature pic for this post.)
22. No 22 – yet to be finished!!
Hopefully you will get to do this walk – clearly I didn’t! although I did get to see some of it because it will go to both High Knoll Fort and The Heart Shaped Waterfall. It is going to be a circular walk from Jamestown. I think it will be a really good addition to the list! Let me know if you do it!
Frequently asked questions about Saint Helena Island?
Q: Where is Saint Helena, Ascension and Tristan da Cunha?
A: All three are in the south Atlantic Ocean. Saint Helena is 1,200 miles west of Angola, and 2,500 east of Rio de Janeiro.
Q: Is Saint Helena a country?
A: No. It is one of the three islands that make up the British Overseas Territory of Saint Helena, Ascension and Tristan da Cunha – a self-governing British Territory.
Q: Do I need a visa for Saint Helena?
A: Unless you have a UK passport, usually yes. Check and apply for an e-visa here.
Q: Is there anything else I need to enter Saint Helena?
A: Yes. You also need a return ticket, pre-booked accommodation, and valid medical insurance. The insurance must be for at least £175,000 and include aeromedical evacuation or other means to pay for treatment. Check your travel insurance covers this or you will have to buy insurance on arrival.
Q: Who lives on Saint Helena?
A: The residents of the island are called Saints – it must be nice to become a saint so easily!
There were no permanent inhabitants on St Helena until 1659 when the British took control, bringing the first slaves with them. Before then, Dutch, Portuguese and British ships had used the island to produce and stock up on food. And a couple of people had lived in isolation here, but there was no permanent settlement. Today the ‘Saints’ are of mixed European (mostly British), South and East Asian, and African descent.
Q: Is that the Napoleon Saint Helena?
A: Yes – it is the island Napoleon was exiled to by the British in 1815, and where he died in 1821.
Q: When is the best time to travel to St Helena?
A: The main tourist season is during the ‘summer’ from December to March (20-32C). However, the seasons are not very distinct on the island and you can have rain in the morning and bright sun in the afternoon at any time of year. It is cooler in the interior.
However, there are a few other things that you have to think about when planning to travel to St Helena – its about what you want to do there:
- For Whale Sharks the best months are January and February.
- For the best visibility for diving and snorkeling and the best marine life – November to March.
- For humpback whales – July to December
- For hiking – the days are longer and typically a bit drier in summer, but all year is possible. The St Helena Festival of Walking is in March.
- For birding – any time of year but it could be considered best during the breeding season from September to February. Migratory birds also arrive in winter which can be another good time.
Travel tips for Saint Helena Island
Getting to St Helena Island
The only commercial airline flying to St Helena is Airlink which flies from Johannesburg to St Helena on Saturdays.
Money
The Saint Helena Pound which is equivalent to the British Pound or the British Pound. You cannot use the St Helena Pound in the UK. The only other place you can use it is on Ascension Island.
The Saint Helena Pound looks similar in shape and size but has different pictures – it makes a nice souvenir.
Bring GBP cash as there are no ATMs on the island and credit cards are not accepted in most places. You can get a cash advance at the local bank (fees apply). The Bank of St Helena also has a Tourist Card which is a prepaid GBP Cash Card. More information is on the Bank’s website.
Internet & Mobile coverage
There has been real internet on the island since 2023. There are a few Wi-Fi hotspots around the island where you can buy internet access. Details are here. You can now also buy a sim – details are here. Check if your accommodation has wifi as well before booking.
Getting around on Saint Helena
By far the best way to get around on the island is by hiring a car. I would recommend a 4wd if you can so that you can get off road on some of the ‘tracks.’
You can also go on tours which can be a great way to learn more about the island, but if you are planning to go hiking or want to see more, then hiring a car for at least a few days is a good idea. There are plenty of car hire options – often your accommodation provider will also have cars for hire. A few things to note are:
- Drive on the left hand side of the road, the same as the UK.
- The speed limit is 30mph except in Jamestown where it is 20mph. Road signs are shown in miles per hour.
- A lot of the roads (most actually) are single lane so it is important to TOOT when coming up to a bend in the road to warn cars coming in the other direction. This does mean you will be tooting a lot!!
- Drive slowly on these roads, and if you meet another car, be polite and give way the best you can.
- If you are going down a hill always give way to cars coming up the hill. (That’s an unwritten rule.)
- Wave to drivers in the other car you are passing. (Another unwritten ‘rule of the road!’)
- You can drive on your overseas licence for up to 3 months.
Car hire, taxis, and public transport is detailed here. Don’t forget to check with your accommodation first if they have car hire as well.
Eating in Saint Helena
The island is covered in eating options and I definitely didn’t get around them all! However, my not to be missed places are:
- The Consulate Hotel for breakfast, dinner, or just coffee,
- The Farm Lodge which is fabulous and thought to be the best food on the island,
- Annes place for the yachtie vibe (obviously I’m going to be biased on that one)!
Richards Travel Lodge, Wellington House and Harris’ Guest House all get the thumbs up too.
Finally, if you love your coffee (I don’t so I’m purely going on friends reports) the St Helena Coffee Shop, down by the port, has coffee you want – fit for a prince as it turns out! (Prince Edward recently visited for coffee.) A great casual setting for breakfast or brunch too.
Where to stay in Saint Helena
Because I arrived and stayed on a yacht, I did not stay in any accommodation, but did get around eating out and did talk to others staying on the island. My summary, taking this into account:
The Mantis is a very popular option and in the historic center of Jamestown. I did enjoy eating here and guests seemed to be very happy with it. The Consulate Hotel – in a mid-18C building was a treat for food and friends that stayed here really enjoyed it.
Banana Tree Lodge is also a very popular B&B and books out with its rave reviews. As said, I did not get a chance to stay here but friends did and loved it! Richards Travel Lodge is another very popular option! Both are out of town and best with a car.
Rock Mount Cottage is a newer apartment out of town close to three postbox walks and would be a great location if you have a car!
Summit View is popular for a whole holiday house. And Whale View St Helena Island is a new option – take a look and see what you think!
Related Posts
Read the Ultimate Guide to stunning Saint Helena Island to find out what you need to know before you come to St Helena
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