Driving around Cape Town

Ha ha. One day or two? Most people around here say 4 days minimum so I would definitely go with 2 days. If you're worried about getting lost in the city, book a room in a hostel. A room give you space in which to be boring while having the better hostel infrastructure for meeting up with other travellers. For Stellies or Franschhoek you won't have that problem as you're going on tours anyway.

With two days in Cape Town, I would do the hop-on-hop-off tour bus with a long stop at Table Mountain to go to the top. And for the second day I would do either a peninsula tour or a Robben Island trip.

I totally agree, 2 days in Cape Town is the absolute minimum. The hop-on/hop-off red bus is a great way to see a lot in one day, as it includes plenty including the lower cable car station for Table Mountain and Camps Bay.

I havent stayed overnight in the Winelands, so dont have a accommodation recommendation there.

My wife and I drove from Cape Town to Hermanus and Stellenbosch (and then beyond). We had a fantastic time.
We stayed at LovanE Boutique Estate outside of Stellenbosch. It was great staying on a wine farm, surrounded by the winelands. They were happy to arrange a taxi into Stellenbosch or to other wine farms so we wouldn't have to drive. The price was very reasonable for what you go, including a great breakfast and wine in your room.

The whale watching is great from the shore in Hermanus but I agree with the above to do the boat trip as well -- you get incredibly close views. There is also good hiking at Fernkloof Nature Reserve.

As far as Cape Town: I don't consider myself a "city person" but I really loved Cape Town. There is so much to do in the city and nearby. I found Robben Island to be a great tour. Table Mountain, Kirstenbosch Gardens and area floral reserves are all great, and you do not feel like you're in a city. There is so much to do -- you will easily fill 2 days.

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