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The Perfect Holiday in South Africa – Our Expert’s Ultimate Two-Week Itinerary

Cape Town needs no sales pitch. Established as a kitchen garden in 1652 to restock ships en route to India, it still replenishes, with picturesque coves carved into a mountainous peninsula, slopes carpeted in an astonishing floral biodiversity, and vineyards that produce the New World’s most underrated wines.

It is easy to be seduced by the city’s cosmopolitan carpe diem lifestyle and spend a few days on safari too, but the Western Cape itself is a wonderful area to explore by car, with looping routes on roads that are relatively traffic-free, and mountain passes linking hamlets that historically served the trade routes.

This is the kind of holiday that invites introspection, the scenery constantly changing around you, the pace of each new discovery entirely in your hands. There are fabulous places to stay, from quirky b & bs to luxury idylls. This two-week tour includes many of my favourite places in the Cape, the Karoo and the Garden Route, and is based on three decades of personal explorations.

I have included three one-night hops in small owner-managed establishments – the distances are not too great, the routes scenic and the welcome always warm. However, if you prefer to reduce these, skip Montagu and spend two nights in Prince Albert (but be sure to take the Swartberg Pass). Or skip Wilderness and head directly for the Crags.

Visitors often ask about safety on the road in South Africa. Rest assured that all my recommendations are made with this in mind, so relax and enjoy the friendliness for which South Africans are renowned.It is not necessary to hire a car for the entire duration. In Cape Town I would recommend employing a private guide, joining a small specialist tour and ordering Uber taxis.

Most tourists visit Franschhoek as a day trip from Cape Town but it’s well worth spending the night there to enjoy the wraparound mountain views, quaint streetscapes and polyglot sophistication of the prettiest valley in the Winelands.

Start your road trip here, heading east to the semi-arid plains of Klein Karoo: this is big-sky country, largely uninhabited and a stark contrast to the more developed and fertile landscape of the Garden Route.

After exploring the lagoons and forests of the balmy coastal strip, head west to spend two final nights in De Hoop, my favourite coastal nature reserve. Part of the Cape Floral Region, a Unesco World Heritage Site, its long vlei and wetlands teem with birdlife and the protected waters are a favoured nursery for hundreds of southern right whales which return annually from June to November to calve and nurse their young here.

There are further highlights I have had to exclude due to time constraints. You could spend a few nights in the delightful village of Stanford, or stay up on the cliff path at Hermanus for the world’s best bed-based whale watching, or take the coastal route via the Hemel en Aarde Valley, its terroir producing the most delicious pinot noirs and chardonnays – but for that you will need to stay another week… which I’m pretty sure you will wish you had.

13 Days
18+ Age
  • Departure

    Main Street, Taiwan
  • Departure Time

    Please arrive by 9:15 AM for a departure at 9:30 AM.
  • Return Time

    Approximately 8:30 PM.
  • Dress Code

    Casual, comfortable athletic clothing, hat and light jacket.
  • Included

    5 Star Accommodation
    Airplane Transport
    Departure Taxes
    Personal Guide

Tour Review Scores And Score Breakdown

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Value for Money