Your LO will love Boulders Beach ? it?s a beach with a penguin colony and little kids absolutely love seeing all the penguins hanging out. It?s on the way to Simonstown. here
I think with a small child, staying on the False Bay side ? Fish Hoek, Kalk Bay etc while you?re doing Cape Town proper, is a better bet as you?ll find that it?s a bit more child friendly, better child beaches, more laid back etc.
Whatever you do though, definitely take some time to explore Kalk bay ? a lovely fishing ?village? around there. There are some great restaurants that vary from cheap and cheerful to very posh and flash. There are also some lovely little markets and craft stores which are great for browsing. The Brass Bell is a Cape Town institution ? huge pub/restaurant over different floors and decks. If it?s lunch time and the weather is nice definitely sit outside on one of the decks. The Brass Bell. Just across the harbour from the Brass Bell is Kalkies ? a fish and chips place that is very cheap and cheerful but everything is totally fresh ? caught by the manager and/or his team that day! Brunch around there is excellent at Olympia café Olympia.
Towards the City, definitely try to go up table mountain ? you can walk it but with a LO you probably want to take the cable car which goes basically from the City to the top of the mountain. Cable Car.
I also highly recommend Kirstenbosch ? Kirstenbosch ? there?s a lovely restaurant and shop and it?s very beautiful. Children love it because there are these gorgeous green slopes to roll down, little streams to throw pebbles into?the list goes on . They also have concerts on Sunday nights which are fantastic and totally worth doing. Concerts You can take or buy a picnic to have as well.
In the City, take time to wonder around the main city and explore greenmarket square ? a very touristy, but nonetheless fantastic African Market.
Obviously, there?s the V&A Waterfront ? basically just shops and restaurants. But in the summer there are always things happening at the open air theatre or just generally around so you can easily pass a day or two there just chilling out.
I would also recommend a trip to Hout Bay. It also have a lovely beach although it?s quite windy. Another cape town institution for food there is called Mariners Wharf www.marinerswharf.com/ and if you are a prawn lover, these are the best prawns you?ll ever eat. And they?ll only cost you a tenner! . There?s also a great market in Hout Bay on Sundays which is good value and very interesting. www.uncoverthecape.co.za/shopping/markets/hout-bay-market/. You should also find all kinds of interesting art shops around there if you?re interested at all. Hout Bay is on the Atlantic side and it?s worth just driving from the city to there ? it?s a gorgeous drive. Camps Bay is the most popular, and richest! beach area in cape town with lots of boutique hotels etc if you'd like to stay there for a while. It tends to be expensive, even by UK standards, so might be worth sticking to day visits. But a visit to the beach there and a walk along the beach would be worthwhile.
For history, it might be worth looking into a walking tour of the city/de waterkant de Waterkant. Also a visit to the old Castle is quite interesting Castle. A trip to Robben Island, where Nelson Mandela was imprisoned is an interesting day out as well ? boats go regularly from the waterfront and you don?t need to prebook normally.
Is this enough? Sorry ? I tend to get a little overexcited as I love Cape Town and wish that everyone could go there!
On the winelands, I?m afraid I?m not nearly as in the know as I am on cape town. You can do organized wine tours which are probably worthwhile (and prevents you driving! ) and of course, if you?re staying in the area it?s easier to wander around. They?re far enough away that I would suggest spending at least 4 days out there, actually staying somewhere.