South Africa · May - October
ST HELENA
An epic crossing of the South Atlantic Ocean from Cape Town, including five days exploring Saint Helena Island
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Overview
Set sail on one of the world’s most extraordinary ocean voyages – a true adventure that few sailors will ever experience. This is your chance to cross the South Atlantic Ocean, discover the remote island of St Helena, and gain the skills, confidence, and miles you need for future offshore expeditions. Whether you’re joining for one leg or the full return journey, this voyage combines hands-on seamanship, incredible destinations, and moments that will stay with you for life. Your adventure begins in Cape Town. You’ll join the crew at the Royal Cape Yacht Club for an intensive “Boat Prep” – learning everything from passage planning and weather routing to provisioning, safety systems, and watch-keeping. It’s an ideal foundation for anyone serious about ocean sailing. We then set sail northwards along the Namibian coast, stopping in the historic port of Lüderitz, where shifting sands hide the haunting desert “ghost town” of Kolmanskop. From there, we turn westward and head out across the South Atlantic Ocean – a true blue-water passage of more than a thousand nautical miles. You’ll experience the rhythm of life at sea and the incomparable beauty of night skies undimmed by land lights. Throughout the voyage, you’ll log valuable ocean miles, including 60 nm skippered passages, ideal for building towards RYA qualifications. Our landfall is St Helena, one of the most remote inhabited islands on earth. Once a key stop for explorers and the final home of Napoleon, today it’s a sub-tropical paradise of emerald valleys, volcanic peaks, and crystal-clear waters teeming with marine life. You’ll spend several days ashore, with comfortable self catering accommodation included, exploring the island’s history, swim with whale sharks, hike through cloud forests, and meet the friendly local “Saint” community. You can choose to fly back from St Helena to Johannesburg or continue with Leg 2 – the adventurous return passage via Tristan da Cunha. This is where ocean sailing becomes pure exploration: powerful seas, celestial navigation, and true self-reliance under expert guidance. It’s challenging, exhilarating, and deeply rewarding – the perfect environment to hone your offshore skills. Whether you join for one leg (around 3 weeks) or the full return (around 6 weeks), this voyage is much more than a sailing trip. It’s a journey of discovery, personal growth, and connection with the ocean at its most inspiring. The full trip covers almost 5,000 nautical miles of sailing.
Highlights
Epic Ocean Sailing
Sail the Atlantic. The REAL Atlantic - not the North Atlantic that “everyone” does. This is the South Atlantic. Massive, desolate and isolated. The return trip is over 4,500 incredible sea miles.
Experience Everything
You’ll get involved in every part of planning and executing a big ocean trip with loads of time for questions and discussion along the way. Perfect for those studying for a qualification, building miles or anyone who wants to experience ‘blue water’ sailing.
Amazing stopovers
Two wonderful stops. The sleepy desert town of Lüderitz with time to visit the ‘ghost town’ of Kolmanskop (Leg 1) and five days on St Helena Island, with accommodation included - a “must see” island. Visit Napoleon's tomb, see the world's oldest living animal or hike the island's subtropical forests. Wavysail crews are always welcomed.
Skippers
Wavy Immelman
Wavy is the co-founder of Wavysail and our lead Skipper. He has patience and experience in equal measure and will ensure you thoroughly enjoy the trip, no matter your previous level of experience. With over 650,000 of Ocean sailing behind him and many years as an RYA instructor to Ocean level, you will be in capable hands from start to end.
Itinerary
Previous
Next
Cape Town
Leg 1: Day 1 to 3 - Prep Week
Your journey starts in Cape Town at the Royal Cape Yacht Club, where we spend the first part of the week preparing or the expedition ahead. You will get to know your fellow crew and the vessel from end to end. We have a detailed checklist, deciding on a Menu plan, shopping, passage planning and much more - there’s a lot to do, but it’s fun and all under expert supervision.
Atlantic Ocean
Leg 1: Day 4 to 7 - Sail Cape Town to Namibia
A gentle sail up the beautiful African coastline. You will get used to the watch system and sailing together. For those who need, you can use this leg for your skippered 60nm passage, or just relax and spot the dolphins that often follow us up the coast.
St. Helena Island
Leg 1: Day 8 - 9 Exploring Lüderitz
We stay a couple of days in the historic, desert town of Lüderitz. Time to relax, stock up for the voyage ahead and also perhaps take a trip out to Kolmanskop - an abandoned German mining town where you can enjoy a guided tour on the town's history and then wander at leisure, exploring the buildings slowly filling with sand.
South Atlantic Ocean
Leg 1 : Day 10 - 17 Sailing to St Helena Island
We set sail for St Helena Island, more than 1,000miles in the middle of the South Atlantic. The weather and sea state tends to be gentle, but this is a true ‘blue water’ passage that will take approximately one week with days, far from the coast, where whales are often our only company.
Saint Helena Island
Leg 1 & 2: Exploring St Helena Island
St Helena remains one of the world’s most isolated places – only accessible by boat until a couple of years ago and still wonderfully remote and unspoilt. Arriving by yacht is the best way to appreciate it. Once ashore, we settle into the cosy self catering cottage included in the trip cost. You can visit Napoleon’s house and indeed his tomb or you can say hello to Jonathan the tortoise, the world’s oldest living animal (190years old!). Relax with a beer in the old-world charm of Jamestown or take a hike into the jungle on one of the ‘post-box’ trails. There is so much to do and see. St Helena always gives Wavysail crew a fabulous welcome – we spend approx. 3 -5 days on the island, before we wave farewell and return to sea.
South Atlantic Ocean to Cape Town
Leg 2 : Sailing the South Atlantic Ocean to Cape Town
The return to Cape Town is a true expedition sail. Heading out into the wild South Atlantic, routing towards Tristan Da Cunha, you will experience every kind of weather. At times, this is really challenging sailing where you will make use of everything you’ve learned so far. Out here is the perfect place to learn and practice Celestial Navigation. We spend time each day on all aspects of sailing theory and practice. We’ve done the trip countless times and know these waters extremely well - so safety will never be a concern but it’s a long leg and when Cape Town appears on the horizon, you will know you have achieved a truly “once in a lifetime” ocean adventure.
What's Included
What's Included
Safety equipment including life-jackets.
All mooring and port entry fees for the boat.
Sailing instruction from a world leading skipper and first mate
Celestial Navigation training and practice
Five nights bed & breakfast on St Helena island
What's Not Included
Transport to the boat
Insurance
Shore excursions
Booking options
Leg 1 - Cape Town to St Helena Island
Your own berth with plenty of space for luggage in a shared cabin onboard
Leg 2 - St Helena Island to Cape Town
Leg 2 is big swells and dynamic sailing conditions. It's all proper sailing. Wet feet and big smiles
Full Trip: Cape Town to St Helena Island return to Cape Town
The full works - 40 days of epic sailing adventure!
Gallery
You'll Be Staying Here
Rocket
"Rocket" is an "Simonis Voogd 55" - a fully kitted out 55 foot expedition vessel, based in Cape Town. She is built for crossing oceans rather than luxury but is spacious and comfortable below and above deck.
You will have your own berth with plenty of space for luggage. “Rocket” has three cabins. Each has a double berth that can be split with lee cloths.
Related Blog Posts
Our Skipper will write a daily blog from the boat each day so Friends and Family can also track progress of the yacht and hear about life on board. They can also send messages for crew to our shore support staff, who will forward to the Aurora via Satellite link once per day.
Exploring St Helena island
By boat to St Helena. Exploring the island and making friends for life
Kelly Rose · Wed 11 Jan 2023
Sail to the desert, Ghost towns and Diamonds in Namibia
Our epic crossing from Cape Town to St Helena Island includes a stopover in Lüderitz in stunning Namibia
Arrival at St Helena
Daily Blog of the Cape Town to St Helena adventure sail - October 2021
On our way home (just 20 days to go!)
Island adventure on St Helena and prepping for home
Calm winds, chocolate brownies and a bit of food safety
The crew discover why food rotation is important
FAQs
Do I need to be experienced in sailing?
We design the trips for a wide range of experience which means that even if you’ve not sailed, our experienced Skippers will ensure you have a fantastic time.
The longer legs will suit “mile builders” who already have some sailing qualifications, and we can spend time supporting you with everything from helming to sail trimming or passage planning as you wish!
Before you join, we’ll ask about your previous sailing experience and what you want to get out of the trip. That way, we’ll tailor the tour to your specific needs.
What equipment do I need?
We supply life-jackets and all safety equipment. You may bring your own foul weather gear, or we can loan you some if required. We send out a detailed kit list before the trip.
What's the cancellation policy?
The group size is kept very small on our trips which gives you a real ‘masterclass’ with our highly experienced Skippers. However, that means each place is valuable and we need full groups.
We ask for a 10% deposit to secure your berth, with the balance being due 6 weeks before departure.
If you cancel your place over 8 weeks out, the deposit is fully refundable. Between 6-8 weeks, we will retain the deposit.
If you cancel 6 weeks or less, the full price will be payable.
Can I keep in contact with friends and family during the trip?
Mobile phones will not work for most of the voyage and Internet connection on St Helena Island is very expensive. However, we actively encourage “Supporters” (friends and family) to join in with your adventure. We create a supporters group and each day, share a Blog, written from the boat. Supporters and crew can exchange short messages via our ship’s email account. Each trip has a dedicated shore contact who will be there for the supporters - answering their questions and making sure they keep fully up to date with your adventure - we often have 150 supporters following the trip!
Can I extend my stay on St Helena Island?
Included in the price of the trip is 5 or 6 nights accommodation, bed and breakfast at the Blue Lantern Hotel.
If we are delayed in departing St Helena Island, Wavysail will cover additional accommodation costs.
If Leg 1 Crew wish to extend your stay, or leg 2 wish to arrive earlier, please let us know in advance. We will book the additional nights for you directly with Blue Lantern at our discounted rate (approx. £50 per person per night). Note that accommodation tends to book up very quickly on the island, so please let us know well in advance.
Likewise, if you wish for friends to join you on the island, let us know and we will arrange this directly with Blue Lantern so everyone is together. You will need to pay Wavysail directly in advance for us to secure the additional times for you. Full details will be shared nearer the time.
What are the best flights to or from the island?
Flights too and from St Helena Island are operated by Airlink. They fly direct to Jo'burg twice per week. Flights do get booked up far in advance so we recommend to book the Airlink flight as soon as you book the Wavysail trip. We are not responsible for your flights too / from the island but of course, will do our best to help in case of any questions.
Dates
4 May - 12 June 2026
FROM$8,378.01 /pp
4 May - 14 June 2026
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20 July - 28 August 2026
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12 October - 22 November 2026
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1 March - 9 April 2027
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3 May - 13 June 2027
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19 July - 29 August 2027
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18 October - 26 November 2027
FROM$8,378.01 /pp