They say life is about the journey, not the destination. That’s why we believe that transportation should be done properly! Why not explore the Cape Peninsula in a helicopter? See Table Mountain from a super yacht, sailboat or jetski? Or how about scaling the vineyard-laden winelands in a 4×4? If you like the joy of driving, why not get out on the open road in a Cobra or a Harley Davidson? We’ve got every option under the sun at your disposal. Each one of these experiences can be booked separately or incorporated into a longer, immersive travel itinerary.



Sailing in Table Bay is easily one of the best ways to get a truly unbelievable Cape Town experience. There’s really nothing quite like making your way towards Robben Island and looking back onto majestic city skyline. Sip on cocktails or frolic in the waves while your skipper barbeques up a storm and preps canapés. Bubbles, crayfish, local delicacies like biltong, South African wines and craft beers. Each sailing adventure can be customised to your own preferences, experience level and timing.


Helicopter Flights to Cape Point, Winelands, and Robben Island

Enjoy a private helicopter flight around Cape Town, the Winelands or the Cape Peninsula. Any of the Explore Sideways tours can be taken to the next level of luxury with the addition of a transfer via helicopter. Depart from Cape Town and venture to one of the amazing estates in the winelands or take a once-in-a-lifetime aerial tour around the amazing Cape Peninsula.


Vintage Cars

The world is so much more beautiful when viewed through the window of a vintage Jaguar, don’t you agree? Explore Sideways has formed an exclusive partnership with a local vintage car collection to offer next-level luxury when exploring the winelands. Options include everything from vintage Bentleys, Rolls-Royces, Mercedes and Jaguars to the lesser known Hudson and Borgward Isabella.


4x4 on Table Mountain

Enjoy a once in a lifetime view of Table Mountain from the only 4×4 allowed to operate within the state park.  Stop near the top at the Block House where you will see uninterrupted views of Cape Town. After a short walk around the historic area, you’ll return to bubbles and snacks. Then make your way to Camps Bay and enjoy uninterrupted views of the 12 Apostles. At your final stop enjoy a picnic style lunch with delicious cheeses, charcuterie and spreads perfectly paired with a wide array of local South African wines.

jet ski in cape town

Jet Ski in Front of Table Mountain

Get an adrenaline-fueled view of Cape Town as you manoeuvre a super powered jet ski. You’ll also have the opportunity to spot dolphins, penguins, and the occasional sunfish up close and personal.

yacht sundowners in cape town explore sideways

Sundowners on a Yacht

A South African “sundowner” is a cocktail that is to enjoyed whilst the sun is setting. Why not sip on sundowners with your friends on your own private yacht?! This exclusive experience will take you from the V&A Waterfront and over to Camps Bay or Clifton where you’ll have a full arrangement of sushi, snacks, cocktails, South African wine and beer. There’s no better vantage point to watch the South African sun go down.


Self Drive a Sports Car

The winding roads and beautiful vistas of the Cape are made for sports cars. Enjoy the beauty of the Cape’s gorgeous coastline. Drive up the West Coast to Langebaan or enjoy a trip to Cape Point. Head out along Camps Bay beachfront, or take in the wine route and amazing farmlands of Paarl and Stellenbosch.

Options (based on availability): Ferrari F430, BMW M4 convertible, Audi R8, Maserati Grancabrio Sport, Ferrari 458 Italia, Range Rover Sport, Cape Cobra, and more. 

Design a tailor-made tour

Allow us to tailor-make a trip around your own personal interests and preferences at no extra cost