Ever wanted to open up on the open road? Feel the wind in your hair? Cruise the coastal road in an exotic sports car?

Explore Sideways is all about immersive experiences and this one is no different. Self drive a luxury or exotic sports car. Choose from a range of majestic vehicles – anything from Audi R8’s to Ferrari’s to Maserati’s and more. Once you’ve chosen your vehicle, hit the open road and enjoy the thrill of being in the drivers seat.

But that’s not all! You also have the option of a fully curated Explore Sideways itinerary based on your interests with all your arrangements taken care of (insider access to off-the-beaten-track locations and exclusive experiences) or go your own way and just enjoy the freedom of being behind the wheel.

When it comes to itineraries choose from a selection of winelands or coastal and let our team know what you’d like to see and do on the day.

How it works:

  1. Choose your vehicle (enquire for options)
  2. Choose from one of the curated itineraries to Stellenbosch, Franschhoek, Constantia and the Cape Peninsula OR allow us to tailor-make an itinerary based on your interests
  3. We’ll make all the pre-bookings, special arrangements and exclusive introductions at specially selected estates
  4. You’ll receive a comprehensive itinerary with all logistics, contacts and information included
  5. Your vehicle will be delivered to your door and collected at the end of your experience

The Details:

  • Flat rate pricing is valid for groups of up to 6pax. Please request a custom quote for groups larger than 7
  • Dinner bookings can be arranged at an extra cost

3 Day Trips From Cape Town By Car

Just in case you need any more inspiration to experience the open roads of the Cape, we’ve put together our top 3 routes for day trips around cape.

Chapmans Peak Drive & Peninsula

There’s a reasons Chapmans Peak Drive is seen in countless car ads. The views you get while you cruise along this coastal feat of engineering are absolutely mind blowing. Starting from Cape Town central take a drive along the M3 to Westlake and the on to the tip of the Cape Peninsula either via the famous Boyes drive with epic views of False Bay, Muizenberg, Kalk bay, Fishhoek and Simonstown or via Ou Kaapse Weg, the old Cape Road into Noordhoek and beyond. When you’ve finished exploring the peninsula make your way back to Cape Town via Noordhoek and onto the celebrated Chapmans Peak Drive. If you time if right you’ll catch the sunset and watch the mountain peaks around you light up in pinks, oranges, purples and reds. Finish of your jaunt with a cocktail in Camps Bay as you catch the last rays of the sun as it slips behind the horizon.


You don’t only have to go wine tasting when you go the winelands. There are plenty of routes to take your driving experience to the next level. If you start in Cape Town make your way via the N1 to the Swartland, Paarl, Wellington or Franschoek for a day of open roads and stunning vista’s. The Swartland is slightly less mountainous than some of the other regions and is more spread out. One of our favourite spots for lunch is Bar Bar Black Sheep or Mama Cucina’s in Riebeek Kasteel. Paarl has a typical Cape Dutch feel about it and a visit to the Taal Monument is well worth an outing. Wellington plays host to several excellent wineries and Jorgenson’s Distillery where you can get anything from Absinthe to African Bitters. A river walk and picnic at Doolhof Winery is also a must when in Wellington. Not to be outdone, Franschhoek plays host to some of South Africa’s top restaurants and is hailed as South Africa’s foodie capital. Take a spin out here and book lunch at any of the world class restaurants (Foliage is one of our favourites). While you’re out there why not book a spa treatment or massage to loosen up before you head home.

Another way of getting to Franschhoek is through the quaint and pretty town of Stellenbosch. Take the N2 and stop for a coffee at De Oude Bank Bakkerij or the Birdcage. The Helshoogte pass takes you up and over through the mountains and past Tokara and Delaire Graff into Franschhoek. If you’d prefer staying this side of the Simonsberg then make your way past Somerset West and go for lunch at The Restaurant at Waterkloof where Chef Gregory Czarnecki works his magic.

Coastal or Inland to Hermanus and the Overberg

Also starting on the N2 is the coastal route to Hermanus. Once you’ve made your way through Somerset West you’ll turn towards the coast and join the Cape Whale Coast Route in Gordon’s Bay. Along this route you can check into great little towns like Pringle Bay, Betty’s Bay, Kleinmond and finishing off in the beautiful old fishing town of Hermanus. The road winds gently along the coastline and if it’s the right time of year you should stop and do some whale spotting along the way. Another spectacular route is to carry on along the N2 through the breathtakingly beautiful Elgin Valley. Stop at the Peregrine Farm Stall or Houwhoek Inn for a coffee and the best pie’s you will ever taste (the jury’s still out on who makes them better). There are countless places to stop in the Overberg region for lunch including the Pool Room at Oak Valley, Fresh at Paul Cluver or a picnic at Gabriëlskloof restaurant or make your way straight to Hermanus for lunch at the Burgundy or Creation wine estate in the Hemel en Aarde Valley.

Contact Us To Book Your Self Drive Experience

Contact us for vehicle availability and options and let us know if you’d like us to work out your itinerary for you – insider access and exclusive experiences included.

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