I had the priviledge of being sent to Africa for a few weeks for a work project, and the co-worker I was travelling with is originally from Cape Town. Our final destination was Lesotho, Africa, however in our failed attempt to wrangle business class tickets for such a long flight, we decided to console ourselves with a 3 day bike trip around the Cape provinces. The above map shows the 2 day loop only as the third day was simply an opportunity for me to check out all the tourist traps.
My co-worker is a bit of a motorcycle nut, and is a hard core Beemer fan so while he has 6 BMW motorcycles (2 sport, 2 vintage, 2 tourers with sidecars) at home, he also keeps a couple BWM's in Cape Town for when he returns twice a year to visit family and friends. It was a perfect scenario for me because it meant that 1) I would be riding with someone who knew the area well, 2) and had a few friends to come along, and 3) I had a late 70's R100RS at my disposal.
Day 1: Meet 3 other riders in Durbanville, then head North towards Malmesbury (95km), have lunch in Ceres (225km), and stop for the night in Barrydale (220km).
Day 2: Ride Southwest through Swellendam (50km), through Caledon (200km), have lunch on the water at one of Betty/Pringle/Gordon's Bay (~75km), then finish up in Parow (75km).