6-day Cape Town, South Africa itinerary

Long-haul → sleep. Base yourself in Sea Point or De Waterkant for walkability, not the waterfront.

Watershed craft market, then dinner at The Test Kitchen Fledgelings (the alumni project).

Cableway up, hike down via Platteklip Gorge if you're fit. Check the weather at 6am — the mountain closes on wind days without warning.

Coffee at Origin, lunch at Chef's Warehouse (walk-in only).

The colored houses. The neighborhood is a real community, not a set — be present about photos of people's homes.

Chapman's Peak Drive → Cape Point → Boulders Beach penguins → back via Simon's Town. Full day. Bring sunblock and layers.

Do the walk to the old lighthouse, not the tram. Ends at the tip of the peninsula.

African penguin colony. Buy the SANParks day ticket if you're doing Cape Point same-day — bundle discount.

Stellenbosch and Franschhoek. 60-min drive from Cape Town. Book a designated driver or the Franschhoek Wine Tram for hop-off tastings.

Lunch with the Simonsberg view. Reserve.

Waterford for the wine-and-chocolate pairing; Reyneke for biodynamic reds.

Book online at least a week ahead. 3.5 hours round-trip from the waterfront. Ex-prisoner guides.

Contemporary African art in the converted grain silo. Heatherwick architecture is worth it alone.

Order a drink at Café Caprice, walk down to the beach for the actual sunset over the Twelve Apostles.

Morning. Tree canopy walkway. Bring a picnic — they permit them.

La Colombe (Silvermist estate) if it's a splurge night; Kloof Street House if it's not.