Expat Health Insurance
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Firstly - it depends where you're from. If you're used to weather in the UK, you'll be surprised by how warm it is in winter, despite the way the locals complain.
Still, although Cape Town's blessed with sporadic mild, sunny stretches in winter, it's not called The Cape of Storms for nothing. There'll be more rainy days than in summer, which rules out trips to the beach. The view from Table Mountain is still gorgeous, but pick a sunny day to go up on the cable car and take heavy coats for the top. It's still possible to visit Robben Island, Seal Island and Boulder's Beach to see the seals and pengins, as long as you dress warm! If you pick a sunny, windless day, you could also play miniture golf in Green Point or in Muizenburg.
Ratanga Junction, the city's only theme park, is closed in winter.
Then there's loads of indoor stuff you can do with the kids. The Two Oceans Aquarium at the V&A Waterfront is open year round, as is the World of Birds and Monkey Park (Hout Bay) and the Scratch Patch (Kalk Bay).
Then there's the usual stuff like cinemas, bookstores and toyshops in malls (at Canal Walk they can ride on a train around the mall).
Grand West Casino and Entertainment World has ice-skating, ten-pin bowling, arcade games, bumper cars, a Lego World and a Barbie World, amoung other attractions, and lots of kid-friendly eateries.