Table Mountain is some 600 million years old. Cape Town has evolved around its magnificent frame with the city spilling through foothills and onto the coast. You will touch down in the Mother City, and will not be able to miss the mountain. It looms large over everywhere, including your hotel at the V & A Waterfront. You will be met at the airport by a private guide who will transfer you to your luxury hotel. It will be located in a mostly pedestrianized area, so you can safely walk around the neighborhood should you wish. Transfers to anywhere in the city are included as part of your stay as well, and dinner reservations have been made for the evening, so you will dine beneath the iconic Table Mountain.

The fast ferry to Robben Island departs nearby your hotel. On this short ride across shark-infested waters, you can sense the island’s isolation and how lonely it must have been out here. You will disembark to meet your guide, a former prison guard who forged a friendship with Nelson Mandela, the site’s most famous inmate. Walking through the prison will only increase your admiration for South Africa’s favorite son, and your guide will help you understand life and history in this austere location. After your Robben Island tour, you can explore more of the V & A Waterfront. This includes charming buildings that have been converted into shops and markets, and the superb Zeitz MOCAA, which is Africa’s pre-eminent contemporary art gallery.

Vibrantly painted houses line the streets of Bo Kaap. Green, purple, yellow, maroon, beige, red, pink, and every color you can imagine line the cobbles. There are more pre-19th-century buildings here than anywhere else in South Africa, and they always have a fresh coat of paint. Once the home of slaves, these houses hold a Cape Malay heritage that is fascinating to explore. After spending the morning in Bo Kaap, you can then find a rich, multicultural history in the city center with your guide who will narrate stories of the African diaspora. There is a great contrast from the old preserved Malay culture of Bo Kaap to the entwined heritage that has been created by a diverse array of African immigrants just two blocks away.

Like yesterday, you can choose your departure time this morning. For the following three days, you will have a private guide and driver, so there will be the opportunity to adjust every day to how you see fit. Today, you travel to Stellenbosch in the Cape Winelands. Rolling hills are draped in vines here, but the mountain views are a highlight here as a rugged peak sits neatly above the old and whitewashed town. After checking into your boutique lodge, you will have a luxurious lunch at a nearby wine farm. Each dish can be paired with a glass of wine as you try the range of local flavors from sparkling MCC to fruity Cabernet Sauvignon and the indigenous Pinotage grape.

Franschhoek is South Africa’s oldest town, which is a charming place that is enveloped by mountains. It is also located some 50 miles from Cape Town, was settled by the French, and has been cultivating wine for over 300 years. You will indulge in a leisurely trip over there this morning with the opportunity to stop at one or two farms along the way. Along Franschhoek’s main street, you will find boutique shops and small cafes in addition to a market and wine tram. While out on this side of the Winelands, you need to try both the sparkling wine and the food. Your guide will have some recommendations that will depend on the flavors that you desire.

More than 200 vineyards can be visited in the Cape Winelands, and your guide can arrange some exclusive experiences for you. For example, you can tour De Waal with the farm owner and grandson of the person who first cloned Pinotage. At some farms, you can taste with the winemaker or cellar master or do a vertical tasting through different vintages. There are farms to indulge in food and wine pairings and also those with more of a focus on the food. While the wines are excellent, the views are even better with all of it being complemented by Stellenbosch’s very serene atmosphere.

From Stellenbosch, the road crosses a mountain before descending to the coast and Hermanus, which is a delightful little town that is famous for its whales. Southern right whales migrate to Walker Bay every July, and the Hermanus cliffside promenade overlooks this bay. When a whale breaches, the whale caller blows on his kelp horn, alerting everyone to the sighting. You can sit on a bench and watch the show with the whales sometimes being just 50 meters from the shore. You can also choose a whale watching cruise this afternoon if you want to get even closer to the whales. Later today, you should find Hermanus to be a quaint town that is filled with small boutique shops and quiet cafes. It is a perennial favorite of South African retirees.

Today’s drive is the longest on your itinerary. It will take you along the coast and Garden Route to Knysna, which will be roughly four hours on a stunning road with continual ocean views. Knysna is another South African favorite for senior visitors. The town is small and pedestrianized with shops and restaurants lining the harbor front. You will have a hotel that overlooks the ocean and will go on a boat tour through Knysna Heads this afternoon. Dramatic peaks stand over the lagoon as you look out towards Indian Ocean waves. Then, your boat will turn around, and you will cruise across languid waters back to Knysna, where there are some brilliant restaurants to try.

Knysna is at the heart of the Garden Route. Within a 45-minute drive, you can be in Wilderness, the Tsitsikamma Forest, Plettenberg Bay, and a number of wonderfully quiet Indian Ocean beaches. Today will be tailored to your interests, and you can visit any of these destinations. You may want a morning on the beach, an afternoon at the shops, and an evening of dining at the harbor. You can also spend a full day in Tsitsikamma, which is where forest-clad cliffs stand over Indian Ocean waves. Plettenberg and Wilderness have superb beaches along with some charming cafes. Another option will be to cross a mountain pass and visit Oudtshoorn, which is a traditional farming town that is home to most of the world’s ostriches.

After an early start, you will transfer to Port Elizabeth for a flight to the Sabi Sands. Your total flight time will be around three and a half hours, and you will land in time for lunch with a view. African safaris are incredibly relaxing, and from your lodge, you can admire the Kruger savannah. Giraffes may poke their heads above the trees while elephants sound their arrival from a distance. You can also see zebra as they graze while the wildebeest scamper past your camp. Lunch will be served as animals drink from a river below you, and you will begin to realize that your safari experience is a mix of wild Africa and contemporary luxuries. It is possible to watch animals directly from your suite, and it is all very safe because a discreet, electric fence keeps the wildlife at a distance. Then, on an afternoon game drive, you will move even closer to Africa’s four-legged giants.

On a morning game drive, you can track a lion pride on the move. Flitting in and out of the grass, these lions will be looking for breakfast, possibly after a disappointing nighttime hunt. Springbok may graze nearby, but these are too small and nimble for lions. You may pass a herd of buffalo, but that would also be a rather ambitious meal for a small pride. Lions are the nemesis of those with black and white stripes, and you can sometimes watch a hunt. You may also be able to see the aftermath, which will be either lions with a fresh kill or scavengers as they battle over what remains.

Prowling predators are a prime example of a wild African safari. In the wilderness, you will experience the rhythm of life, and that includes the brutal and beautiful interactions between animals. You will see monkeys and baboons as they stand guard for antelope because the primates howl when any cats are in the vicinity. Interactions play out at watering holes and rivers as well, sometimes with more than ten species drinking together at one time. You can take a picnic to these scenes and can also dine on a deck beneath the stars after your game drives. Again, it is this mix of authentic African excitement and laid-back luxuries that makes South Africa such a unique place to visit.

Over these two days, you will go on morning and afternoon game drives with the option of a nighttime game drive. Drives are usually under three hours and explore a compact and private reserve. Vehicles and visitors are restricted, so this Sabi Sands reserve never feels crowded. However, the reserve is unfenced and truly wild, so you can come to understand how wildlife behaves in a landscape that has remained mostly unchanged by human hands. The game drives will be complemented by downtime at your lodge, and here, you can dip in the pool, sip wines on a terrace, and feel the tranquility of the legendary Greater Kruger savannah.

After your morning game drive, you will be transferred across the savannah to a small airstrip. From here, you will fly to Johannesburg for a day in Soweto. Home to the anti-apartheid struggle, this township was where Mandela and others made their name. The streets remain as colorful and vivid as Mandela’s time, but the times have changed, and there is now a real positivity to Soweto. On a private tour, you will first visit the Apartheid Museum before moving onto Vilakazi Street and Mandela’s former house. From here, you can meet with some of the locals, sample traditional township food, and develop a sense of the history that took place beneath your feet. Rather than stay in Soweto, you will spend your final night in Sandton, which is at Nelson Mandela’s former retreat.

This morning will be at your leisure before you are transferred to O.R. Tambo International Airport for your outbound flight.