Welcome to South Africa
A land of rugged beauty, unique wildlife, diverse cultures, friendly faces, opulent vistas and world class wine and cuisine. With such a range of incredible choices it can be hard to know where to begin, that’s where we come in.
Explore Sideways takes all these ingredients and distills them into a lifetime travel experience.
Your Itinerary
Explore the best of South Africa’s top destinations in this bespoke, luxury itinerary and stay in the most exclusive South African retreats.
Spoil yourself at your luxury private urban retreat in Cape Town and make the most of the curated experiences in this city known for its diverse beauty and award-winning restaurants.
Discover and unwind in the bucolic Cape Winelands, known for its picturesque mountain ranges, world class wine farms and restaurants. Fly into your extraordinary safari experience in the Kruger National Park and explore this precious African treasure.
End your South African journey in the vibrant and multicultural Johannesburg.
Let your luxury African travel experience begin…
Cape Town – 4 to 5 nights
21 Nettleton
Welcome to a private patch of heaven suspended between ocean, mountain and African sky. This exclusive urban retroffers uninterrupted privacy and 5-star service in a magnificent clifftop mansion – choose from our five suites or spectacular penthouse. Each room is individually appointed with bespoke art, antique furniture and luxurious soft furnishings – styled in a modern fashion. The expansive gardens with their gigantic granite boulders, swimming pool and terraces, offer tranquillity in an undisturbed setting. With the back opening onto the Table Mountain Nature Reserve, a World Heritage Suite, this allows our guests private access to the hiking trails up Lion’s Head, Signal Hill and Table Mountain.
With services included such as a fully inclusive breakfast and bar, afternoon tea, evening canapes and sunset cocktails and more…
What we love about it
Popular Explore Sideways Experiences in Cape Town
Best of the Cape Peninsula Tour
Enjoy a breathtaking journey around the Cape Peninsula and Cape Point and capture picture-perfect photos from every angle...'from the waves to the winelands'
From / person- Full Day Private Tour
Curated Cape Town City Tour
Explore the majestic city of Cape Town and discover it's hidden gems while ticking off the best of your bucket list
From / person- Full Day Private Tour
Street Art & Community Walking Tour
Get an authentic view of Cape Town on this tour of the Khayelitsha township and street art walking tour
From / person- Full Day Private Tour
Great Whites & Great Wines – Shark Cage Diving & Wine Tasting Tour
Experience an adrenaline pumping day cage diving with great white sharks followed by a leisurely lunch and wine tasting
From / person- Full Day Private Tour
Go beyond with luxury and unique add-ons
Your Next Stop
Cape Winelands – 2 nights
La Residence
La Residence is situated in the Franschhoek Valley on a 30-acre estate filled with vines, fruit trees, flowers and herbs. It is a romantic and indulgent paradise whose magnificent interior is filled with rich fabrics, wonderful artwork and antique furniture. Eleven individually-decorated suites designed by Liz Biden enjoy vibrant colour schemes and spectacular views. Palatial en-suite bathrooms ooze glamour. On hot days, the shimmering infinity pool beckons. Sip drinks under a shady umbrella, or relax with treatments in the Spa.
Five minutes’ drive from the charming curio shops and galleries of Franschhoek village, the hotel provides complimentary transfers so guests can explore at their leisure..
Service is warm and personalized: an atmosphere of ease and relaxation pervades. Fresh produce from the garden and fine local wines create memorable dining experiences.
What we love about it
Popular Explore Sideways Experiences in Winelands
Best of the Cape Winelands Tour (Stellenbosch & Franschhoek)
Discover the breathtakingly beautiful views and vistas of Franschhoek and the world class-wines of Stellenbosch during this luxury, private tour.
From / person- Full Day Private Tour
Winelands Horse Riding Adventure
This tour takes you off the beaten track and out of your comfort zone - buckle up and enjoy the ride.
From / person- Full Day Private Tour
Family Winelands Adventure
Wine tasting and fun for parents and children. Animal encounters, grape juice tastings, jungle gyms and play areas. A great day out for the whole family.
From / person- Full Day Private Tour
Ultimate Franschhoek Foodie & Wine Tour
Taste excellent food and superb wine from some of the best estates in South Africa’s culinary capital, Franschhoek.
From / person- Full Day Private Tour
Go beyond with luxury and unique add-ons
Your Next Stop
Sabi Sands/ Kruger National Park – 3 to 4 nights
Singita Boulders
Boulders Lodge has a contemporary air of tranquillity that honours Africa in an authentic way. Inspiring the name Boulders was an enormous boulder that sat right in the middle of the place where the wine cellar was to be built. A simple decision was made to build the cellar around the boulder! Guests can enjoy wrap-around views from most parts of the natural stone lodge, and the lookout deck offers the perfect spot from which to observe wildlife drawn to the Sand River. The quiet pond alongside the thatched lounge area allows the light and the landscape inside to the wide open spaces.
Singita Boulders Lodge offers twelve suites, all with their own en suite bathroom and shower, outside shower, private heated swimming pool, double-sided fireplace, mini bar and fridge, room mini safe, air-conditioning, overhead fans, private lounge, direct dial telephones and game-viewing deck.
What we love about it
Your Final Stop
Johannesburg – 1 to 2 nights
Fairlawns Boutique Hotel & Spa
It’s an urban sanctuary in the area of Sandton, with close attention to detail and exceptional service. The chic, upscale suites are individually decorated in varying themes, each featuring every desired modern amenity. Indulge yourself in their culinary experience.
What we love about it
Popular Explore Sideways Experiences in Johannesburg
Curated Johannesburg City Tour
Visit the extraordinary South African City of Gold, Johannesburg. Visit a multitude of unique local galleries, explore new urban centres and experience the thrilling pace of this vibrant African city as it goes through a new stage of renewal and development.
From / person- Full Day Private Tour