Overberg road-trip: Wine, whales and the tip of Africa

Leave Cape Town early and follow the N2 towards Hermanus, then turn onto the R320 for a full day in the Hemel-en-Aarde Valley. Pinot Noir and Chardonnay are the headline varieties across its three cool maritime appellations. Bouchard Finlayson is redoing their cellar door, so bookmark this one for the future, but book Hamilton Russell in advance for a focused introduction to Chardonnay and Pinot Noir, or choose Newton Johnson for a broader tasting in the Upper Hemel-en-Aarde Valley. 

For lunch, book ahead at Creation Wines on the Hemel-en-Aarde Ridge. Its multi-course food-and-wine experiences centre on the estate’s cool-climate range and locally sourced ingredients, making it a proper meal rather than a quick cellar-door stop.

If you’d prefer something more relaxed, I love the bistro-style fare at Mogg’s Cookhouse, or head to Bosman Hermanus where The Frame House serves tastings and light plates overlooking vineyards, proteas and indigenous vegetation. Fancy a walk? The hour-long Koppie Trail climbs to offer wide views across Walker Bay.

Babylon’s Tower Cottage sits on a working apple-and-pear farm at the foot of the mountain that gives it its name, high in the Hemel-en-Aarde Valley and overlooking Creation. The self-catering cottage is perfectly positioned for uninterrupted valley views, with a spacious patio and easy access to walks through the orchards and indigenous fynbos. The farm dams also offer swimming when the weather’s warm. Hermanus is about 15 minutes away by car, but the appeal is the rural setting: stock up before check-in and plan to cook, braai and stay put for the evening.

After breakfast on the stoep drive down the valley to Hermanus. The town’s 12-kilometre Cliff Path runs between the New Harbour and Grotto Beach, but a shorter section around the Old Harbour, Gearings Point and the town centre delivers excellent coastal views without taking over the day.

From roughly June to November you’ll be scanning Walker Bay for Southern Right whales, but even outside the season the path remains worthwhile for its rocky coves and coastal fynbos. For a closer marine encounter, book a whale-watching trip from the New Harbour. Sailings are weather-dependent, so keep the Cliff Path as a backup. On Saturdays, the Hermanus Country Market runs from 9am to 2pm, with local food, produce and crafts. Otherwise, perhaps for lunch beside the tidal pool at Ficks before continuing east on the R43.

Stanford is about 30 minutes away. Park near Queen Victoria Street and explore the heritage village on foot. The Wandelpad follows the Klein River and loops through shaded parts of town, while the self-guided heritage route highlights historic cottages, churches and Market Square. On Saturdays, visitors can also browse the morning markets in the square and on the Stanford Hotel stoep. Allow time to browse Queen Victoria Street’s small shops and galleries, or book in advance for the Lady Stanford boat cruises on the Klein River.

Finish with a wine tasting at Stanford Hills Estate, where the cellar door and Casa Cello (expect Portuguese-inspired dishes) overlook the vineyards and dams. From the village, it is a ten-minute drive to Stanford Valley Estate, leaving time for a swim, a spa treatment or a short fynbos walk before dinner.

This is one of my favourite places to stay in the Cape. Set on a 440-hectare country retreat beneath the Akkedisberg, accommodation ranges from terraced en-suite rooms to freestanding cottages, several with kitchenettes, indoor and outdoor fireplaces, private stoeps and walled gardens.

Well-marked hiking paths through fynbos lead to viewpoints, and guests have access to a 16-kilometre mountain-biking network. There is also a swimming pool, an Overberg-focused art gallery and the Poplar Country Spa, with a sauna, steam room and plunge pool. You could drive into Stanford for meals, but it is better to book dinner at the Manor House, where the seasonal menu draws on contemporary country cooking and regional produce.

Leave Stanford Valley early for the coastal road to Elim. Moravian missionaries founded the village in 1824, and its historic centre includes the whitewashed church, the old water mill and a heritage centre devoted to the mission station and its community. 

Then head east to discover the southernmost vineyards in Africa. These maritime vineyards are particularly known for Sauvignon Blanc and Syrah. Strandveld Vineyards and Black Oystercatcher both offer wonderful tastings.

Continue to Agulhas National Park and the iconic Cape Agulhas Lighthouse precinct, which was recently revamped. There’s an interactive centre worth a look, and a vertigo-inducing climb to the top of the lighthouse for great coastal views. Then walk the one-kilometre boardwalk to the coast and the marker at Africa’s southernmost point, the official meeting place of the Atlantic and Indian Oceans. If you have extra time, it’s great fun to wander the coast, peering into rock pools, until you reach the rusting remains of the Meisho Maru 38 wreck.

Then, back in your car, head to Struisbaai. Walk along the harbour wall, watch the fishing boats come in, and look for the wild Short-tailed stingrays that sometimes enter the shallows at the quayside. 

This is something of a secret spot, and I’m not sure I should be sharing it. But here goes anyway. Langrug Lodge is a secluded self-catering cottage on the banks of Soetendalsvlei. Built in 1912 and later restored, the house sleeps six (at a squeeze, four is better) and is fully equipped for an independent stay. It is entirely off-grid, with a wood-fired donkey boiler for hot water and gas for cooking. Low-key but well-equipped. The setting is simply magical, with views across the vlei and farmland. You can explore the farm at leisure, from long walks to canoeing on the vlei. Indoors, there are deep baths and fireplaces suited to cold Overberg winters, while outside there is space to braai alongside the wood-fired hot tub. Struisbaai is about 10 kilometres away, but it’s best to arrive with all your groceries and settle in for the night.

Plan to be in Bredasdorp around 9am for a visit to the Shipwreck Museum (open Monday to Friday only), where anchors, figureheads, navigational equipment and recovered objects explain why the Agulhas coast became known as a graveyard of ships. 

Then head inland via Napier (do stop at the excellent stall) and Caledon before driving through rolling hills to Greyton. On a Saturday, you’ll find the village market in full swing from 9am to noon on the Main Road green, bringing together local produce, preserves, baked goods and ready-to-eat (second) breakfast.

Leave the car parked and explore on foot. Wander along the tree-lined streets to see Greyton’s Cape vernacular cottages, Victorian houses and still-functioning leiwater channels.

Along the Main Road, you’ll find independent shops and galleries, with no shortage of charming restaurants. For coffee or a light vegetarian lunch, stop at Pure Café; for a longer country-style meal, book at Abbey Rose.

Set aside the afternoon for the great outdoors. Greyton Nature Reserve begins at the edge of the village and offers a network of marked routes, including the Gifkloof, Gobos and Platkloof trails. A gentler alternative is the village Leiwater Walk, followed by a short drive to Genadendal. Founded in 1738, it is Africa's oldest Moravian mission village: pop in at the church precinct and the Genadendal Mission Museum before returning to Greyton for the night.

Slap-bang in the heart of the village on Greyton’s Main Road, The Post House is within easy walking distance of the market, restaurants, cafés and village trails. Built in 1860, the building began as a trading post and lodging house before incorporating the local post office. Today you can choose from 16 refurbished rooms and suites. There are also two guest lounges, delightful gardens and a swimming pool for guests. And did you know: the pub here made a famous appearance in that famous Bell’s whisky advertisement!

After a leisurely breakfast at The Post House, check out and head west towards Caledon and the N2. Your first stop is Dassiesfontein, the much-loved farm stall, where you'll find a  rambling collection of antiques, enamelware, cast-iron stoves and farm goods. The restaurant is also a good option for coffee, cake or a traditional country lunch.

From Dassiesfontein, continue towards Cape Town. For one final Overberg detour, turn off at Bot River for a wine tasting at Beaumont Family Wines, housed on a historic farm beside the Bot River, or keep going up and over the pass with the Mother City in your sights.