South Africa isn’t called the rainbow nation for no reason – it is literally a melting pot of colourful cultures, interesting languages, delicious flavours and diverse experiences. There’s simply so much to see and do that it can be a bit daunting if you’re planning a visit. That’s why we’ve curated our top 5 ultimate South African experiences for you to ensure you get to experience the best our country has to offer in 2020.

4×4 Wine Tasting Experience

If you’re in Cape Town and a lover of fine wine, then the Winelands should be top of your activities list. Known the world over as some of the best value-for-money wines located in the most picturesque locations, the Winelands cannot be missed. Luckily, this doesn’t necessarily mean you need to arrange an entire day trip out to the smaller outer-lying regions of Stellenbosch and Franschhoek.

Klein Constantia, located within the Constantia Wine Valley in Cape Town, is one of the oldest wineries in the area.  This scenic 146-hectare wine estate features a tasting room open year-round, and we’ve curated a special tour to give you an insider’s perspective of the wine estate’s vineyards and property on a custom-built safari-style 4×4 land cruiser.

Venture out to a beautiful lookout deck, where the tasting room manager will explain the history and heritage of the estate over a bottle of the estate MCC (local sparkling wine). After the bubbles, you’ll make your way down to the cellar and barrel room for a cellar tour and specially tutored wine tasting in ‘Dougies Dungeon’, the MCC maturation cellar specially designed for private tastings like this one. The tasting will include a sample of the world-famous Vin de Constance, known to be the sweet wine of choice for many historical figures including Napolean, Churchill and the Queen of England. At the end of the experience, there will be snacks and canapés to compliment the wine before making your way back to town.

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4×4 Wine Tasting Experience

Explore a historic Constantia wine estate by 4x4, followed by a full wine tasting and delicious canapés as you look over the breathtakingly beautiful valley below.

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  • 2 - 3 hours

Cape Peninsula Fynbos Foraging & Picnic with the Penguins

The Cape Peninsula is exceedingly beautiful and offers a window to some of the most fascinating biodiversity on the planet. From the fynbos on the mountainside to the marine life of the ocean rock pools, there is endless beauty all around you. On this unique adventure, you’ll learn about indigenous edibles as you find them in nature and learn how to forage for them in a sustainable way. Once you’ve finished foraging, you’ll end off the day by stopping at Boulder’s Beach – home to a colony of thousands of African penguins. African Penguins used to be known as jackass penguins because of their distinctive braying, and they’re the only penguins found on the continent. The penguins first came to False Bay in 1983 from Dyer Island, which is near Gansbaai.  While the penguins are here all year, summer time is definitely the best time to tick this off the top 5 ultimate South African experiences list. 

Rates include: Pickup and drop-off from your accommodation in and around Cape Town, private guide/driver, all entrance and activity fees as stated, foraging experience, 3 course meal with paired local wines.

Sunset Sundowners on a Private Yacht


Is your out of office set? Are you ready to enter true ‘holiday mode’? Then treat yourself to something truly luxurious and special with our Private Luxury Sunset Cruise . It’s anchors away from Cape Town’s iconic Victoria and Alfred Waterfront, where the private yacht will set sail. The yacht will then head along the coast of the city, floating across the azure blue waters of the Atlantic from where you can enjoy watching the sunset along the horizon with the Cape mountains as a spectacular backdrop. You’ll be served a sundowner cocktail and delectable canapés. The 3-hour ocean excursion is the perfect complement to end off any day tour or visit to the Mother City. If you’re celebrating a special occasion, note that the cruise can accommodate up to 8 guests.

Rates include: Pickup and drop-off from your accommodation in and around Cape Town, private guide/driver, activities as stated, sundowner cocktails and canapés.

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Private Luxury Sunset Cruise

Relax and enjoy unbelievable views of Cape Town from the comfort of a 12.8m luxury motor yacht.

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  • 3 Hour Private Experience

The Joburg Experience

Johannesburg, Jozi, the city of gold or ‘Egoli’: call it what you will, this city is vibrant and full of energy, brimming with exciting activities.

Rooftop Yoga in Berea with Stephen Heyman 

Start your day by doing revitalising Rooftop Yoga in the suburb of Berea as a backdrop with Stephen Heyman as your instructor.  Stephen is originally from Belgium and found a new home in South Africa since 2006. Until recently he was working in the corporate world, traveling around Africa to start up new offices for a Belgian supply chain company. He then decided to trade in his desk for a yoga mat to start teaching yoga to corporate companies and bring some welcome exercise and stress relief to offices in Johannesburg.

Cradle of Humankind Visit With Historian

Next up, head to the ‘Cradle of Humankind’, a World Heritage Site located about an hour outside of Johannesburg or Pretoria. This paleoanthropological site currently occupies 47,000 hectares, where the Sterkfontein Caves were the site of the discovery of a 2.3-million-year-old fossil, Australopithecus africanus (nicknamed “Mrs. Ples”), found in 1947 by Robert Broom and John T. Robinson.

Taste of Yeoville with Diana Nje

Complete a full day with an evening stroll with one of our local guides through the heart and heritage of Rockey Street in Yeoville. The walk includes some spectacular views, forgotten Victorian architecture and rich political heritage, to accompany the tasting journey. We break the meals up by including a lovely market exploration that has a predominantly West African influence.

Hidden Gems Winelands Tour


Do you want to escape the crowds and go off the beaten track? Then our Hidden Gems Winelands Tour could be just the kind of breakaway you might be needing. We’ve rounded up some local speciality spots that are frequented by those in the know. Start off the day in the Stellenbosch region with a wine tasting of the hearty, historic reds of Muratie Wines. This historical, cobwebbed cellar is tucked away in the exquisite Knorhoek Valley and run as a family business under the stewardship of owner Rijk Melck. Next, you’ll head further into Stellenbosch, toward the naturally-formed amphitheatre between the Helderberg and Stellenbosch mountain ranges to visit Keermont Vineyards, a boutique wine estate known for their Syrah and their white blend, Companion. After a tasty lunch,  explore the foothills of the Klein Drakenstein Mountains just outside Franschhoek with a visit to Lynx Wines – one of the smallest wine estates in the valley – to taste the reds that made the winery famous before ending off the day at the prestigious Oldenburg estate. Located in the mountains in an area known as Banghoek, this boutique winery offers Cabernet Sauvignon, Cabernet Franc, Syrah, Merlot, Chardonnay and Chenin Blanc. 

Rates include: Pickup and drop-off from accommodation in and around Cape Town with private guide/driver, 4 wine tastings

Rates exclude: Lunch, additional beverages and gratuity  

*Please note that because these are small production, boutique wineries this itinerary is subject to change and may include a different winery than stated based on availability.

Wine & Food
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Hidden Gems Wine Tour

This exclusive tour will take you to the wine estates less well known, but producing some of the most sought-after wines the region has to offer.

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  • Full Day Private Tour

If you would like to experience one of these top 5 ultimate South African experiences, speak to one of the Explore Sideways experts. We proudly curate and convene private tours for local and international visitors, and look forward to giving you a trip of a lifetime!

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Want to know more or have any questions, let an Explore Sideways expert help you plan an experience you will never forget!