Cape Town and the Winelands
Six days of Cape peninsula and Cape wine, timed around the wind and the harvest.
Food & Wine · 6 days · February to April
Do not book the cableway. Hold Table Mountain for the first morning the southeaster drops, and fill the other mornings with the peninsula run — taken anticlockwise from Hout Bay, so the sea is on your left down Chapman's Peak and you reach the penguins after the coaches have turned for home. The wine half works better from the Banhoek Valley than from Franschhoek village: you sit between both towns and drive twenty minutes to either, rather than committing to one main street. Come in February or March and you are there for the harvest.
Day by day
- Day 1
The Signal Hill side of town
An easy landing day on foot in the old city, then the Silo District in late light.
10:00Bo-Kaap
The colour is the least of it: this is the quarter freed slaves and Cape Malay artisans built, and the Bo-Kaap Museum on Wale Street explains why it is still fighting to stay.
Chiappini and Wale Streets are people's homes, not a set — ask before photographing a doorway.
14:30Zeitz MOCAA
Heatherwick carved a cathedral out of forty-two concrete grain tubes, and the building is worth the ticket even before you reach the largest collection of contemporary African art anywhere.
- Day 2
The mountain, on the first still morning
Go up early if the wind allows, then eat in Woodstock rather than back at the Waterfront.
08:00Table Mountain Aerial Cableway
Treat this as a movable feast rather than a booking: the top is flat, walkable and worth three hours on a clear day, and worth nothing in cloud.
The cableway shuts in high wind and reopens without notice — check tablemountain.net the night before and again at 07:00, and buy online to skip the ticket queue, not the boarding one.
12:30The Old Biscuit Mill
Woodstock is where Cape Town's kitchens actually cook, ten minutes from the centre and a world away from the harbour-front menus.
The Neighbourgoods Market runs Saturday mornings only; the restaurants in the yard trade all week and are calmer for it.
- Day 3
The peninsula, anticlockwise
South down the Atlantic side, round the point, back up the False Bay shore for the penguins.
08:00Chapman's Peak Drive
Nine and a half kilometres cut into a vertical cliff — driven southbound the ocean is on your side of the road and every lay-by is a left turn.
Tolled, and closed outright after heavy rain or rockfall; the boom is at the Hout Bay end, so check before you commit to the route.
10:00Cape Point
Walk past the funicular to the old lighthouse and keep going to the new one: the crowd thins to nothing within ten minutes and the cliff path is the reason to be here.
Baboons at the car parks will open an unlocked car in seconds — nothing on the seats, windows up, and do not eat outside.
14:30Boulders Beach
An African penguin colony that has colonised a suburban beach, and by mid-afternoon the tour buses have gone back to the city.
The Foxy Beach boardwalk is the viewing colony; the Boulders side is the one you may swim from.
- Day 4
Constantia, the oldest vines
Two farms that predate everything in Stellenbosch, and the garden below the back of the mountain.
10:00Klein Constantia
Vin de Constance is the wine Napoleon had shipped to Saint Helena and Jane Austen wrote into a novel — this is where the vines it comes from still stand.
Tastings are seated and booked; the Vin de Constance flight is a separate booking from the standard one.
12:30Groot Constantia
South Africa's oldest working wine farm, founded in 1685, and the Jonkershuis terrace is the right place to sit out the hottest part of the day.
15:30Kirstenbosch National Botanical Garden
A garden that only grows plants indigenous to southern Africa, running straight up into the fynbos on the mountain's eastern flank.
The Boomslang canopy walkway is at the top of the garden, a steady twenty-five minute climb from the entrance — allow for the walk back down.
- Day 5
Over Helshoogte into the vines
A long lunch on the pass, then the oak streets of the old town below it.
12:00Delaire Graff Estate
Lunch on the terrace looks down the whole Banhoek Valley to the Simonsberg, which is the single best sit-down view in the winelands.
Two restaurants share the estate — the Terrace for the view, Indochine for the cooking; both book out weeks ahead in February and March.
15:30Dorp Street, Stellenbosch
The longest surviving row of Cape Dutch and Victorian frontage in the country, and a real university town underneath it rather than a wine-tour stage set.
- Day 6
The Franschhoek valley, slowly
A morning in the walled garden, an afternoon at the table, and back to the airport.
09:00Babylonstoren
Eight acres of formal fruit and vegetable garden laid out on the geometry of the Company's Garden — and everything on the lunch menu is picked within sight of the table.
Garden entry is ticketed and capped, and the guided garden walk needs booking days ahead in high season.
13:30Boschendal
A 1685 farm working as a farm again — the vegetable and pasture programme feeds the kitchen, and it sits directly on the road back to Cape Town.
The Werf restaurant is the serious one and books ahead; the Deli under the oaks takes walk-ins.
Questions
- How long is the Cape Town and the Winelands itinerary?
- The Cape Town and the Winelands itinerary runs 6 days and covers 14 stops across Cape Town, Simon's Town, Stellenbosch, Franschhoek.
- When is the best time to do the Cape Town and the Winelands itinerary?
- February to April is the best window for the Cape Town and the Winelands itinerary.
- What happens on day one of the Cape Town and the Winelands itinerary?
- Day one is the signal hill side of town: An easy landing day on foot in the old city, then the Silo District in late light.
Sources
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