Cape, Winelands & Madikwe

Day 1 — Arrive Cape Town

Your flight lands at Cape Town International, where a Wesley Chapel Travel welcome and a private driver are waiting to bring you the short way into the city, Table Mountain filling the windshield as you go. You’ll settle into the Victoria & Alfred Hotel, set right on the V&A Waterfront, with the rest of the day yours — to catch your breath, walk the harbor, or take in the mountain over a first glass of Cape wine.

Day 2 — Cape Town by mountain and city

After breakfast a private guide collects you for the cableway to the top of Table Mountain (weather permitting) — the whole city, the bay and the peninsula laid out beneath you, the best way to get your bearings on day one. From there you wind through the Bo-Kaap, the historic Cape Malay quarter with its cobbled lanes and hand-painted houses, before the afternoon opens up back at the Waterfront at your own pace.

Day 3 — The Cape Peninsula

A full private day down one of the most beautiful coastlines anywhere: the Atlantic seaboard past Camps Bay and Llandudno to the working harbor at Hout Bay, on to the Cape of Good Hope inside Table Mountain National Park, and a stop at Boulders Beach — the one place on earth you can stand a few feet from a colony of African penguins. Lunch is at Kalk Bay’s Harbour House, the surf breaking under the windows, before an easy drive back to the city.

Day 4 — Cape Town at leisure

A day with nothing on it, which after long-haul travel is its own kind of gift. Linger over breakfast, take a harbor cruise or a sunset sail, visit the Zeitz museum of contemporary African art, or slip away for a spa afternoon — or do none of it and simply enjoy the Waterfront. Milli can arrange anything you’d like in advance.

Day 5 — Into the Winelands

A short transfer east brings you to Stellenbosch, South Africa’s oldest wine town, with a brief orientation through its oak-lined streets and Cape Dutch gables. You’ll settle at the Spier wine estate — a working farm since 1692, with a spa, an art collection and vineyards in every direction — and have the afternoon free to taste, wander, or do nothing at all.

Day 6 — A day among the vines

The day is yours in the Winelands, with a vehicle on hand whenever you want it. Spend it tasting through the estates around Stellenbosch and Franschhoek, lingering over a long lunch, or staying put on the farm — this is the slow middle of the trip, the pause before the bush.

Day 7 — North to Madikwe

After breakfast you fly from Cape Town up to Johannesburg, where you’re met and driven out to the Madikwe Game Reserve — a scenic road transfer of about four and a half hours across the highveld, or an optional light-aircraft charter if you’d rather trade the drive for a short hop. Madikwe is malaria-free and one of the largest reserves in the country; after lunch and time to settle into your suite, you head out on your first afternoon game drive as the light turns gold.

Days 8–10 — On safari at Madikwe

Your days fall into the unhurried rhythm of the bush — a pre-dawn wake-up and coffee, a morning drive into the cool early air when the animals are most active, a long lazy middle of the day for brunch, the pool, the spa or the view over the waterhole, then an afternoon drive that runs into sundowners in the field and a spotlight search on the way home. Madikwe holds the Big Five along with cheetah, brown hyena and one of Africa’s most important populations of endangered wild dog, and because it’s a private reserve your guide can leave the road to follow a sighting and drive after dark — the game viewing a national park can’t offer. Between drives there are guided bush walks, stargazing under some of the darkest skies in southern Africa, and long dinners around the fire.

Day 11 — Homeward

One last morning drive and a final breakfast before you’re transferred back to Johannesburg’s O.R. Tambo airport, met and helped through check-in for the flight home — the red dust of the reserve still on your boots.

Prefer the leopards?

Madikwe is our malaria-free safari — the easy choice if you’d rather not take anti-malarial tablets. If your heart is set on leopard country, we build this same Cape Town and Winelands journey with its final nights in the Sabi Sand instead: Kruger’s most storied private reserve, with some of the highest leopard densities in Africa and a shorter, one-hour transfer from the airstrip to the lodge. The trade-off is honest — the Sabi Sand sits in a malaria area, so you’d take the precautions your doctor recommends. Tell Milli which you’d prefer, and she’ll put the right version in front of you.