Cape Town & the Winelands

1 day, 6 stops

Cape Peninsula day

Photo: South African Tourism from South Africa / Wikimedia Commons, CC BY 2.0

A long sightseeing day, not a gentle toddler itinerary. Leave early and keep Hout Bay brief so Cape Point remains the main morning outing. Chapman’s Peak’s official site displayed CLOSED when checked on 14 November 2026: this coastal leg is conditional (check before you go). If closed, use Constantia Nek and Ou Kaapse Weg, allowing extra time.

Suits: For two

Day 1 Around the Peninsula

123456© OpenStreetMap contributors
  1. Morning

    Hout Bay Harbour

    Hout Bay

    Start with a brief harbour look, then continue south. Save boat trips and a long breakfast for another day.

    Photo: South African Tourism from South Africa / Wikimedia Commons, CC BY 2.0

  2. Morning

    Chapman's Peak Drive

    Hout Bay

    Only take this toll road if the operator confirms it is open. Stop only in designated parking areas. If closed, omit this stop and follow the inland route in the blurb.

    Photo: dconvertini / Wikimedia Commons, CC BY-SA 2.0

  3. Morning

    Cape Point

    Cape Point

    Continue to Cape Point for the main outing. Use viewpoints near vehicle access if walking is difficult; the lighthouse approach includes stairs, so it is not a continuous pushchair route.

    Photo: Cape Hatteras National Seashore / Wikimedia Commons, Public domain

  4. Lunch

    Cape Point

    Cape Point

    Eat within Cape Point before leaving the reserve; confirm current food service and bring backup snacks (check before you go).

    Photo: Cape Hatteras National Seashore / Wikimedia Commons, Public domain

  5. Afternoon

    Boulders Beach

    False Bay

    Use the Foxy Beach penguin-viewing boardwalk with a pushchair. This is a viewing stop, not time set aside for swimming or scrambling over boulders.

    Photo: Wayne77 / Wikimedia Commons, CC BY-SA 3.0

  6. Afternoon

    Kalk Bay

    False Bay

    Make a brief final stop only if there is daylight and energy left, then return to Cape Town. Pavements and harbour edges need care with a pushchair; skip this stop if earlier delays mount up.

    Photo: Octagon / Wikimedia Commons, Public domain

Perfect pairs on this trip

A thing to do and a ranked lunch nearby, for a slower half-day.

See all 12
  • Cape Point, on the way back, about 16 min (estimate)

    Cape Point, then Simon’s Town

    1. MorningCape Point
    2. LunchBertha's Tier 3

    Leave the park and stop for lunch in Simon’s Town on the way back. Allow extra time for the park roads.

  • Hout Bay, about 13 min drive (estimate)

    Hout Bay and Massimo’s

    1. MorningHout Bay Harbour
    2. LunchMassimo's Tier 3

    Explore the harbour, then head to Massimo’s for a meal during its confirmed service.

  • False Bay, about 6 min drive (estimate)

    Boulders and Simon’s Town lunch

    1. MorningBoulders Beach
    2. LunchBertha's Tier 3

    See the penguin colony before a meal in Simon’s Town.

  • False Bay, In town

    Kalk Bay and Kalky’s

    1. MorningKalk Bay
    2. LunchKalky's Tier 4

    Explore Kalk Bay and stop for a casual harbour meal.