The villages of Rooi Els, Pringle Bay, Betty's Bay and Kleinmond share a common history, from the ancient heritage of the early Khoikhoi people, to a safe haven for smugglers in the 1800's, whalers in the early part of the 1900's, and then stock grazing before developing as holiday and retirement villages. The area is part of the Kogelberg Biosphere Reserve, an internationally recognised conservancy because of the incredible variety of plants found here: an estimated 1650 species, mainly fynbos. The Harold Porter National Botanical Garden in Betty's Bay offers a showcase of this diversity. The colony of African penguins at Stony Point is also a great drawcard.

Kleinmond lies at the mouth of the Bot River Vlei, an important wetland which is also home to a herd of feral horses that have adapted to life in the marshy conditions. The horses may occasionally be spotted during walks or canoe trips along the estuary.

Past the Arabella golf estate the road connects to the R43, which takes one over the Bot River to Fisherhaven, the private resort of Merensee and the historic fishing village of Hawston, long the home of abalone fishermen. Follow the coast to Vermont, Onrus, Sandbaai and Hermanus, famous for southern right whales and "champagne air".

At the Sandbaai turnoff to the right, the road to the left leads to the Hemel-en-Aarde ("heaven-and-earth) Valley, originally home to a leper colony, but now renowned for high-quality wines produced in the cool coastal climate.

Hermanus was originally named Hermanuspietersfontein, after a itinerant teacher from the 1830’s who grazed his sheep near a freshwater spring in what is now Westcliff. Fishermen from Hawston started to settle here more than 150 years ago, but the town gradually became known as a holiday resort and grew into the main coastal centre of the Overberg. It now has a vibrant tourism industry, boasts a large number of art galleries and restaurants, and is, amongst others, home to an annual Whale Festival (24-27 September 2009). From about June to November, especially the area around the Old Harbour and Gearing's Point offers excellent opportunities for watching whales, which often come to within metres of the rocks. The Cliff Path, which stretches for more than 10 km from the New Harbour to the mouth of the Klein River, affords another way of watching whales, as well as enjoying the fynbos, rocky cliffs and white beaches along the way. For nature lovers there is also Fernkloof Nature Reserve, where 1474 plant species have been identified. Hermanus boasts a 27-hole golf course, and the yacht club is based on the Klein Rivier Lagoon, on the road to Stanford.

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