We did a similar trip a few years ago now, but we stopped in Plettenberg bay (about half way between PE and cape Town) and stayed at a wonderful B&B called Bosavern (it's still operating - I checked). Up on the hill, overlooking the bay and at the right time of year you can watch whales. There are whale watching trips and there's a seal colony in the bay. Read my journal post abut the experience here: http://journals.worldnomads.com/philsylvester/story/58691/South-Africa/Whale-watching-in-South-Africa
Phil about 6 years ago
Hi, we did exactly this trip in December last year. I highly recommended getting a copy ((free) of Coast to Coast when you get to Cape Town - it's full of backpacker style places to stay- although some are more flashpacker and nice and quirky. They have copies in most hostels. I wrote a blog on places to stay and things to do which you can find at www.atptravels.com - just click on blog, scroll down to South Africa and there's lots of info there - for Cape Town: http://atptravels.com/the-cape-coast-according-to-doug-and-harri/
In addition, for winelands I can highly recommend going to Stellenbosch & Frankschhoek (stop at Moreson vineyard and Boschendal in particular (you can reserve a picnic hamper and eat in the grounds accompanied by wine - amazing food), or eat at the amazing Quartier Francais (Frankschhoek) (pricey) and stay at Otter's bend. Ride an ostrich in Ooudtshoorn, have drinks overlooking the waterhole in Buffelsdrift, visit the Cango caves. Go to Knysna and find the Austrian bakery - it does the world's best portugese tarts or have a huge fish skewer at 32 degrees South. If you like adrenalin activities - around Storm's River there is tons to do - the world's highest bungee jump, ziplining over waterfalls etc. Surf at Jeffrey's bay.
So jealous of you doing this - I could do it all over again, so much to explore in this area!
Happy to give more detailed info... over 5 years ago