Five days lets you properly split time between Cape Town's city sights, its dramatic coastline, and the wine country less than an hour away — a rare combination of city, ocean, and vineyard that's worth structuring an itinerary specifically around. Days 1 and 2 stay in the city. Table Mountain deserves a clear-weather morning — the rotating cableway climbs to the flat summit in under ten minutes, but the mountain is occasionally closed in high wind, so build in flexibility and check conditions before committing to a specific day. The views from the top extend over the entire city, Robben Island, and the coastline in every direction. Spend the rest of day one at the V&A Waterfront, and use day two for Bo-Kaap's colourful streets and a deeper exploration of the City Bowl's neighbourhoods. Day 3 covers the Cape Peninsula, best done as a full-day loop rather than rushed. Boulders Beach's African penguin colony is a genuine highlight and surprisingly close to the city, followed by the dramatic cliffs of Cape Point, where the Atlantic meets the Indian Ocean. The drive along Chapman's Peak between these stops is itself one of the most scenic coastal roads in South Africa, worth slowing down for rather than treating purely as transit time. Day 4 is for wine country. Stellenbosch and Franschhoek, both under an hour from the city, offer tastings set against mountain backdrops that genuinely rival Napa or Tuscany. Plan a relaxed day with two or three winery stops rather than trying to cram in more — quality of experience matters more than quantity here, and lunch at one of the wine estates is typically worth building the day's schedule around. Day 5, if you have it, is best spent on beaches and a slower pace after four fuller days. Camps Bay or Clifton beaches in the morning give a different coastal experience from the peninsula's wilder scenery, and a sunset dinner overlooking the Atlantic is a strong way to close out the trip. A few practical notes: use Uber rather than hailing taxis directly, both for safety and reliability. Book Table Mountain access ahead where possible, since the cableway can sell out and closes in high wind regardless of advance bookings. And consider renting a car specifically for the Peninsula and wine country days, since both offer far more flexibility than organised tours for exploring at your own pace.