Two Sides of Cape Town: Where history, adventure and wine meet

Cape Town has a way of making every day feel like a different journey. One moment you’re standing high above the city on an ancient mountain, the next you’re sipping wine in a centuries-old vineyard, watching penguins waddle along a beach or hearing stories from people who lived through one of South Africa’s darkest chapters.

As part of South African Tourism’s Mega Lekker experience, travel writers Carolyne Jasinski and Helen Hayes explored different sides of the Mother City on different itineraries. Carolyne was travelling with Bench Africa and Helen was with Adventure World.

Here we talk about all that’s on offer – from its dramatic landscapes and rich history to its food, wine and vibrant waterfront life.

A city beneath a mountain

The first landmark that demands attention is Table Mountain, the flat-topped icon that dominates Cape Town’s skyline.

Helen discovered that the journey to the top is almost as impressive as the view itself. The rotating cable car climbs steeply up the mountainside, slowly revealing sweeping views across the harbour, city and coastline.

When the famous “tablecloth” of cloud rolls over the summit, it spills across the mountain like fabric draped over a table.

At the top, the views are unforgettable, stretching from Robben Island to the beaches and coastal suburbs below.

Among the rocks are some unexpected residents: dassies, or rock hyraxes. They may look like oversized rodents, but these small creatures are surprisingly related to elephants.

For those wanting an adrenaline rush, there’s even the chance to abseil down the mountain face. For everyone else, the restaurants, walking trails and endless photo opportunities provide plenty of reasons to linger.

A tip: the queues for the cable car can be long, so a VIP ticket can be worth considering.

The heart of the city

Down at the V&A Waterfront, Cape Town’s energy shifts from mountain adventure to urban buzz.

The waterfront is where locals and visitors mingle among cafes, restaurants, markets, live music and street performances.

The new Oranjezicht Market showcases the best of local produce, from biltong and Cape Malay curries to fresh fruit, handmade crafts and South African wines and gins.

It’s also home to one of the city’s most charming attractions: a colony of resident sea lions. Their unmistakable smell announces their arrival before they appear, but visitors can now watch them safely from a purpose-built enclosure where they can rest away from the crowds and slip easily back into the water.

For Carolyne, the waterfront was the perfect place to soak up the atmosphere – and perhaps pick up a few irresistible souvenirs, including baby clothes for her new grandchildren.

Remembering Robben Island

From the waterfront, ferries carry visitors across the bay to Robben Island, a place that leaves a lasting impression.

This is where Nelson Mandela spent 18 of his 27 years imprisoned during apartheid.

Carolyne’s Robben Island tour begins as a bus ride around the island’s buildings, but the experience becomes much more powerful when the guides reveal they are former prisoners themselves. They share personal stories of being jailed, sometimes simply for protesting, and describe life inside the prison.

The most emotional moments come when visitors see the cramped cells and sleeping conditions, including the small cell where Mandela lived.

While Mandela is recognised as an extraordinary figure, the guides emphasise that he never wanted to be separated from the other prisoners. His story is part of a much larger struggle.

The message from those who experienced it first-hand is one of forgiveness rather than revenge … a reminder of the importance of learning from history.

Cruising the coastline

Helen’s moving experience came in a very different form: a ride with Cape Sidecar Adventures.

Climbing into a vintage sidecar motorcycle, complete with leather jacket, she travelled along the coast towards Hout Bay and Chapman’s Peak Drive.

The winding road delivered spectacular views over cliffs, ocean and beaches, passing through coastal favourites including Camps Bay and Maiden’s Cove.

The vintage bikes – some with wartime history – added a touch of nostalgia and made the journey as memorable as the destination.

Carolyne encountered the same spectacular coastline on the Cape Peninsula Tour, which revealed both natural beauty and fascinating history.

At Maiden’s Cove, she learned how the area had once been the only beach where black South Africans were permitted during apartheid. They transformed the rocky cove into a beach escape, building rock pools that still exist, and creating a place of beauty from difficult circumstances.

Further south, the tour continues to Cape Point and the Cape of Good Hope, where visitors can climb to the lighthouse or take the funicular for spectacular ocean views.

Along the way, there are ostriches, dramatic landscapes and the famous Boulders Beach, where African penguins steal the show.

A taste of South Africa’s wine country

Beyond the city, Cape Town’s wine regions offer another reason to linger.

Helen explored Constantia, South Africa’s oldest wine region, visiting Klein Constantia, a vineyard dating back to 1685.

The property’s history is as rich as its wines, including the legendary sweet Vins de Constance, once enjoyed by Napoleon and admired by Jane Austen.

A scenic tasting among the vines revealed the beauty of the region, where some steep slopes are still worked by horses.

Carolyne explored Stellenbosch and Franschhoek, beginning with a wine and cheese pairing at Fairview Winery, where she discovered Pinotage – South Africa’s signature grape variety.

Light, fresh and perfect for warm weather, Pinotage became the perfect souvenir to take home.

In Franschhoek, the wine tram offers a fun way to explore the region’s cellar doors, while Lanzerac provided a memorable stay among vineyards and history.

Dating back to 1692, Lanzerac combines old-world charm with luxury, offering wine tastings, beautiful views, restaurants, pools and even a chance to learn about the surprising differences in bottled water through a water tasting experience.

Where to stay

Cape Town and its surrounding wine regions offer accommodation to suit every style, from historic wine estates to contemporary waterfront hotels.

For Carolyne, the highlight was staying at Lanzerac Hotel & Spa in Franschhoek. The historic estate blends centuries of heritage with modern luxury. The property’s story is woven into everything from its original farm buildings to the exposed brickwork that hints at structures dating back into the 1500s.

Set among vineyards and gardens, Lanzerac is a destination in itself. There are seven pools, expansive lawns, restaurants, terrace dining, a café and a library, making it easy to spend days exploring the grounds.

Wine is, of course, at the heart of the experience. Guests can enjoy tastings with knowledgeable guides such as brand ambassador Francois Dutoit, who brings the estate’s history and wines to life. A highlight is the viewpoint tasting, where glasses are paired with sweeping views across the valley.

For Helen, the peaceful escape of The Claremont Boutique Hotel offered a very different experience. Located on the quieter side of Table Mountain, the boutique hotel feels worlds away from the bustle of the city, with gardens, heritage architecture and views across the surrounding landscape.

Originally built in 1928, the property retains the charm of its history while offering contemporary comfort. Close to Kirstenbosch National Botanical Garden, it’s a favourite base for guests who enjoy wandering through the gardens and exploring the natural beauty of the area.

The hotel features individually styled rooms, a beautiful restaurant, a sunny morning lounge and an African-inspired safari lounge filled with books and design details that reflect the continent’s heritage. It’s the kind of place that encourages guests to slow down, perhaps with a glass of wine in the afternoon or a quiet moment overlooking the gardens.

For something completely different, Carolyne also experienced the energy of Radisson RED Cape Town V&A Waterfront, right in the heart of the waterfront precinct. With its warehouse-style design, polished concrete floors, bold spaces and rooftop bar, the hotel has a youthful, creative feel. It’s not just a place to sleep – it’s a place to be part of Cape Town’s social scene.

Together, these stays capture the diversity of the region: vineyard estates steeped in history, peaceful garden retreats and a waterfront hotel where the city’s modern pulse is always on show.

*This story originated from an interview on Travel Writers Radio