How do you experience the best South Africa has to offer in a two-week trip? By following the ultimate itinerary created by our expert Pippa de Bruyn

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.

The itinerary

Day 1

Depart from the UK on an overnight direct flight from Heathrow to Cape Town with British Airways.

Cape Town

Day 2

In just over 11 hours you will arrive in Cape Town (BA flights land between 7am and 11am). Check into Kensington Place, a boutique hotel on the slopes of Table Mountain with great city views. Freshen up and walk or take an Uber to the Table Mountain cableway. Ascend the cliffs of the city’s most famous landmark and enjoy a bird’s-eye view as the lights flicker on and the sun sinks into the Atlantic. Head back to Kloof Street or Bree Street, which have the highest concentration of restaurants and bars: both are near your hotel. For succulent fresh fish, you can’t go wrong with Miller’s Thumb (0027 21 424 3838). If you want to add people-watching to the menu, the bohemian opulence of Kloof Street House attracts a good crowd (0027 21 423 4413).    

Day 3

Explore the peninsula on a tour with Clive de Bruyne (ZAR 3,800/£203 for two). A circular drive takes you south along the east-facing False Bay coast to Cape Point, then back north along the west-facing Atlantic seaboard, finally snaking along the cliffs of world-famous Chapman’s Peak drive. Clive will tailor the itinerary to your interests. Kirstenbosch Botanical Gardens, a seamless integration of the manicured and the indigenous, is definitely worth including, and a visit to the penguin colony at Boulders is virtually obligatory. Lunch is usually at a seaside table at Harbour House, preceded by a stroll around the cobbled streets of Kalk Bay.

Day 4

Experience a different aspect of the city by joining one of Uthando’s small-group tours to visit a few inspiring community projects in the townships. A non-profit initiative, Uthando invests all tour profits back into the local community. (Around ZAR 2,800/£148 for two).

Depending on the time of year, your guide Xolani Maseko can drop you off at the V&A Waterfront in time to catch the last ferry to Robben Island (3pm in summer) to see the cell where Nelson Mandela was imprisoned for 18 years. Online pre-booking is essential.

Afterwards, stroll the bustling Waterfront area; Willoughby’s (0027 21 418 6115) serves the best sushi in the city. 

Day 5

The Winelands

Stephen Flesch, the notable wine guide (ZAR 3,600/£190 for two) picks you and your luggage up at around 9am for a wine tour of Stellenbosch and Franschhoek. Itineraries are personalised but all strike a great balance between iconic and off-the-beaten-track vineyards, and the lunch venue is always spot on.

At the end of the day Stephen will drop you off at Leeu House in Franschhoek, a relatively new boutique property located right in the heart of the village.

Day 6

Spend the day exploring the Franschhoek valley utilising the hop-on-hop-off wine tram (the departure point is near Leeu House). It’s a very convivial experience; pre-booking is advised. There’s no need to taste at every stop, but you’ll get a real sense of the 18th-century farmhouse architecture and see some gorgeous landscapes. 

If you’re interested in vintage cars, set aside time to visit the Franschhoek Motor Museum. Have your hire car delivered to you in the afternoon.

Day 7

Klein Karoo and Montagu

Take a leisurely drive east, through the Franschhoek Pass and the fruit-growing farms surrounding Villiersdorp to join the R60, then the R62 to the village of Montagu (just under two hours away). Here, many houses still have vineyards and orchards in their back yards.

Check in with Lauren and Louise at Vineyard Country House. If they’re serving dinner, stay put as Louise is an excellent self-trained cook. Alternatively, book at Simply Delicious, a short stroll away (0027 23 614 3483). 

Day 8

Great Karoo and Prince Albert

Fortified by Louise’s gourmet breakfast, set out on the four-hour drive (without stops) to Prince Albert. The R62 passes through the semi-arid Klein Karoo, where most of the Cape’s award-winning fortified wines and brandies are produced. Stop to sample the Tinta Barocca at Boplaas Family Wines in Calitzdorp. About nine miles out of Calitzdorp, take the Buffelskloof/Kruisrivier turn-off – a scenic little shortcut – before ascending the Swartberg, one of the most hair-raising and jaw-dropping mountain passes in the country, to reach Prince Albert. 

Stay the night in one of the town’s finest properties, the Rosenhof Country House, a lovingly restored farmhouse with its own pub, wellness centre and art gallery. Try to arrive in time to take afternoon tea in the rose garden, but leave some room for the excellent dinners in the Rosenhof ’s restaurant.

Day 9

Garden route: Wilderness

Take a stroll around the village to admire the Victorian-era streets, then take the Meiringspoort pass to Wilderness, a two-and-a-half-hour drive south, and check into owner-managed Moontide Guest Lodge, a collection of thatched cottages each with its own entrance on the banks of the tidal Touw river.

Tim or Maureen will discuss dinner options and book your table (Joplin’s steakhouse is a must – unless you’re a vegetarian).

Day 10

Garden route: the Crags

Keep heading east on the N2, a pleasant coastal route that traverses the region’s lakes and lagoons to Knysna.

It’s just under an hour direct to Lairds Lodge Country Estate, but stop first in Knysna to explore its pretty estuary, either aboard the Oyster Boat, armed with a glass of white wine and fresh oysters, or on a more serious eco-our cruise along the coastline.

Have lunch at East Head Café. In the afternoon, take a Woodcutter forest walk with Mike Dixon, whose knowledge and passion is inspiring – who knew there was so much to learn from the trees? Dine at Hog Hollow; its communal evening meals are fun. 

Day 11

Visit Birds of Eden, the largest free-flight aviary in the world, to marvel at the brilliant hues of the 280 species at home here. Lunch amid the vines at Bramon Wine Estate. Afterwards, meet South Africa’s elusive smaller cats, such as the caracal and serval, at Tenikwa Wildlife Awareness Centre where you can also join a small group to help exercise cheetahs born in captivity. Or simply enjoy the serene atmosphere and indigenous-forest views from the poolside at Hog Hollow. 

Day 12

Grootbos Private Nature Reserve

A leisurely five-hour drive west brings you to the Grootbos Private Nature Reserve, home to two award-winning lodges, and famed for its extraordinary fynbos heathland, winter whalewatching, beach excursions and unrivalled ocean views.

Day 13

Be sure to take the guided marine walk today; times are dependent on the tide (book on arrival). Wear a swimsuit – the water is warm and the limestone-backed coves and beaches are a delight to explore. Be sure to stroll the vlei at sunset; quad-biking (done in a small section of the reserve) is also surprisingly easy and a lot of fun.

Day 14

Allow three hours for the drive back to Cape Town International airport. British Airways overnight flights direct to London depart between 6pm-9pm.

When to travel

Cape Town’s peak summer season – the hottest time – is between Christmas and March. In April, the temperatures are balmy, the light is softer, the Cape Doctor (the south-easterly wind that howls through the city) is dormant and the sunsets are spectacular.

The temperate winter usually starts in June. Sunny days alternate with downpours which water the winter-flowering fynbos, including proteas, lilies and aloes.

July to November is the time when the southern right whales migrate to calve and nurse, providing the best land-based whale-watching in the world. Note that July and August can be wet, but the climate remains temperate on the Garden Route where rainfall is often at night followed by calm, sunny days. This is the best time to visit the semi-arid Klein Karoo.

From October to early December the coastline sparkles in the spring sun with the occasional bout of rain. This is when some of the best deals of the summer season are to be had.

How to book

The above itinerary can be arranged independently, but you may find it easier to employ the services of a tailor-made South Africa specialist. Telegraph Travel recommends Audley, Kuoni and Trailfinders.