Walk the 12km cliff path from New Harbour to Grotto Beach during whale season (Jul-Nov). Whales breach and tail-slap 30m below you. Free. The best land-based whale viewing in the world.
The tiny Bot River wine ward has 6 cellars within 5km. Beaumont and Wildekrans are standouts. Tasting R50-R80. Combine with lunch at a route restaurant. Zero tourists compared to Stellenbosch.
A 200-year-old whitewashed fishing village still inhabited by descendants of the original fishermen. No entry fee, no gift shop -- just walk the sandy lanes between thatched cottages and watch the boats come in.
The whale capital. Best land-based whale watching in the world (Jul-Nov). 12km cliff path, excellent restaurants, and a growing wine scene on the Hemel-en-Aarde Valley. The most developed Overberg town -- hotels, galleries, markets. 90 min from Cape Town via the N2.
Victorian village with the best Saturday market in the Overberg. Klein River Cheese, craft beer at Birkenhead Brewery, and riverside dining. Quieter and cheaper than Hermanus (20 min east). The Klein River kayak trip is a hidden gem.
Twin coastal villages on the Kogelberg coast. Kleinmond has wild horses and the Palmiet estuary. Betty's Bay has the Stony Point penguin colony and Harold Porter Botanical Garden. Both are self-catering destinations -- bring your own food.
Great white shark capital. Cage diving in Shark Alley year-round. Also: De Kelders cliff caves, Walker Bay whale watching, and the Danger Point lighthouse. Raw, wild coastline. The harbour restaurants serve the freshest fish in the Overberg.
Tiny wine village on the R43 between Kleinmond and Hermanus. Six cellars within 5km. Beaumont and Wildekrans are the stars. The annual Bot River Barrel Run festival is a local institution. Combine wine tasting with lunch at one of the route restaurants.
The quiet ends of the Overberg. Arniston has the Kassiesbaai fisherman's village and the Waenhuiskrans cave. Rooi-Els is a handful of houses on a rocky cove between Betty's Bay and Gordon's Bay -- the most isolated village within 90 minutes of Cape Town.