Three years before Simon van der Stel was granted the land that became Groot Constantia, a German immigrant widow named Catharina Ras walked into his office and asked for a piece of ground at the foot of Ou Kaapse Weg. Ras had buried five husbands by then – at least three under suspicious circumstances – and was, as Steenberg's own marketing acknowledges, "one of the Cape's most daring, controversial settlers." Van der Stel granted her a lease on 25 morgen of land in 1682, three years before he took Groot Constantia for himself. In 1688 the lease became a freehold title. That makes Steenberg the oldest legally-titled wine farm in South Africa, three years senior to its much more famous neighbour up the hill.

Steenberg today is best known for two grape varieties: a savagely good Sauvignon Blanc (especially the Black Swan and the Magna Carta blend) and the unusual Nebbiolo – Steenberg is one of only a handful of South African producers working with this notoriously difficult Italian variety. The estate is part of the Graham Beck Enterprises stable, with a sleek modern tasting room, an excellent bistro, and the highly-rated Catharina's Restaurant on the property. The award-winning Steenberg Hotel sits on the same grounds for those who want to make a night of it.

On 13 July 1685, Simon van der Stel – VOC governor of the Cape, second man in the colony after the Commander himself – was granted 891 morgen (763 hectares) of land behind Table Mountain. He named it Constantia, possibly after a daughter of his patron Rijkloff van Goens, possibly after the Latin constantia (steadfastness), possibly after the VOC ship of the same name. We will never know. He built a manor house in late Dutch Renaissance style, planted vines, and within a decade was producing wine that, after Hendrik Cloete bought the estate in 1778, became the most famous sweet wine in the world.

The roll call of Grand Constance drinkers reads like a Wikipedia disambiguation page. Napoleon had thirty bottles a month shipped to St Helena from his arrival in 1815 until his death in 1821. Frederick the Great of Prussia bought it at auction. Louis Philippe, King of the French, was a regular customer. King George V drank it. Otto von Bismarck drank it. The fictional roll call is just as long: Jane Austen's Mrs Jennings prescribes it as a cure for a broken heart in Sense and Sensibility (1811); Charles Dickens serves it to Reverend Septimus in his last, unfinished novel The Mystery of Edwin Drood; and Charles Baudelaire compares it to his lover's lips in Les Fleurs du Mal.

The 1925 fire that destroyed the manor house was so complete that "more complete burn out could scarcely be imagined", according to the architect Franklin Kendall who restored it. The current building dates from his 1926 reconstruction. The famous slave bell cast in 1716 – one of the oldest bells in the Cape – was stolen from the estate on 2 September 2024 and has not been recovered.

When Simon van der Stel died in 1712, his Constantia estate was divided into three. The smallest piece – "Klein" Constantia, "little" Constantia – was the part that retained the most prestigious vineyard land, planted on decomposed granite at altitudes of 70 to 343 metres above sea level, with cooling ocean breezes off False Bay. Today its 146 hectares produce, on a measured global comparison, one of the most acclaimed sweet wines in the world: Vin de Constance.

Vin de Constance is the modern reconstruction of the historical Constantia dessert wine that Napoleon drank. It was recreated in 1986 by the late Ross Gower, working with retired Stellenbosch University viticulturist Professor Chris Orffer and the Jooste family who bought the estate in 1980. Made from Muscat Blanc à Petits Grains (Muscat de Frontignan), with around 10% of the crop deliberately raisined on the vine before harvest, it sells today at auction for R44,555 per single 500ml bottle (1986 vintage, Strauss & Co, June 2025) – making it one of the most expensive South African wines on any secondary market.

On a more sober note: the estate acknowledges its history. Walking into the tasting room you pass a wall-mounted historical installation that traces the lives of the enslaved people who worked the original vineyards. Klein Constantia is one of only a handful of Cape estates that has chosen to do this. There is also a kramat on the property – a Muslim shrine, one of three in the area, marking the burial place of one of the Cape's exiled Muslim holy men.

The third piece of Van der Stel's original Constantia grant, separated from Klein Constantia in 1796 and given the deliciously Dutch name Buitenverwachting – "beyond expectation" – by its then-owner Cornelis Brink. Today Buitenverwachting is the wine farm that locals quietly tip you off to: less famous than Groot Constantia, half the price of Klein Constantia, with the highest visitor rating of any estate in this guide (4.6 stars on Google across 422 reviews).

The wine tasting is housed in the original 250-year-old cellar with whitewashed walls and a thatched roof. The signature wine is the Buiten Blanc, a Cape blend of Sauvignon Blanc and Sémillon that has been in production for decades and is a regular feature on Cape Town wine lists. Their reconstruction of the historical Constantia dessert wine is called 1769, after the year the original recipe was perfected by Hendrik Cloete. The estate's restaurant has held a place on Cape Town's "best restaurant" lists for over twenty years.

Boschendal sits on Helshoogte Pass between Stellenbosch and Franschhoek, on land granted in 1685 to Jean le Long, a French Huguenot fleeing religious persecution after the revocation of the Edict of Nantes. The arrival of the Huguenots in 1688 transformed Cape winemaking – they brought with them the viticultural knowledge, work ethic, and varietal preferences of the Loire and Rhône valleys. Boschendal – "wood and dale" in Dutch – is one of the most complete surviving Huguenot-era wine estates in the Cape.

The current manor house dates from 1812 and is one of the most beautiful examples of Cape Dutch architecture in the country – H-shaped, broekie-lace gabled, painted brilliant white against the dark vineyards. Boschendal is now part of a much larger lifestyle estate, with the Werf Restaurant (a destination in its own right), the casual Deli, the famous Boschendal Night Market on Friday evenings between October and April, and a small luxury hotel (Werf Cottages) on the property. The 2024–25 expansion added picnic-friendly lawns and an artisanal farm shop.

On the floor of the Eerste River valley, 30 kilometres east of Cape Town and a kilometre off the N2 highway, sits a long avenue of palm trees leading to one of the most photographed Cape Dutch homesteads in South Africa. Meerlust – "love of the sea", a reference to the False Bay views from the manor's upper windows – was founded in 1693 by a German immigrant named Henning Hüsing. The estate has been in the same family, the Myburgh family, since 1756 – making it one of the longest-held private wine estates in the world, with eight generations of continuous family ownership.

Meerlust is, more than anything else, a one-wine estate. Rubicon, first released in 1980 by the late Hannes Myburgh and his cellar master Giorgio Dalla Cia, is a classic Bordeaux-style blend (Cabernet Sauvignon, Merlot, Cabernet Franc, sometimes Petit Verdot) that essentially invented the modern category of premium South African red wine. It has been produced every vintage since 1980 (with rare exceptions in poor years) and is the wine that opens almost every serious South African wine list. The 2018 Rubicon, which scored 95 points from Tim Atkin MW, is the current benchmark.

On 1 February 1700, Willem Adriaan van der Stel – son of Simon, who had succeeded his father as Cape governor that same year – granted himself 30,000 hectares of land at the foot of the Hottentots-Holland mountains east of Cape Town. He called it Vergelegen, "situated far away", reflecting how distant the property felt from the colony. Within six years he had built a manor house, planted half a million vines, established cattle stations, dug reservoirs and irrigation canals, and accumulated a personal fortune that drew the attention of the VOC in Amsterdam. In 1706 he was sacked for corruption, ordered home in disgrace, and the estate was broken up and sold off.

Vergelegen has the highest Google rating of any estate on this list (4.7 stars across 1,861 reviews) – and it earns it. The five Camphor trees Willem Adriaan planted in 1700 are still alive on the property, declared National Monuments in 1942, and are believed to be among the oldest documented exotic trees in South Africa. The walled garden was originally built high enough to keep lions out (a real concern in the 1700s). The estate has been owned since 1987 by Anglo American – the multinational mining group – and the resulting investment in the gardens, restaurants, and cellars has been substantial.

Today Vergelegen offers four restaurants on the property – from the casual Stables Bistro to the destination Camphors at Vergelegen – plus a famously elegant picnic basket experience served at long communal tables on the lawn between the camphors. The cellar produces consistently award-winning Bordeaux-style reds (the Vergelegen V flagship and the GVB White are the wines to ask for) and the gardens, with their octagonal walls, sundial, and historic specimen trees, are among the most visited in the Cape.

The fourth and final fragment of Simon van der Stel's original 1685 Constantia grant, Constantia Uitsig – "Constantia view" – sits on lower-lying ground than its three sister estates, with sweeping vistas across the Constantia Valley to False Bay. While Klein Constantia, Buitenverwachting, and Groot Constantia all retained their pre-1776 winemaking continuity, Constantia Uitsig was used as grazing land for much of the 19th and 20th centuries, with serious wine production resuming only in the 1980s under owner David McCay. The current cellar – a striking glass-and-steel structure where you can watch the barrels through the walls – dates from a 2010s redevelopment.

We include Constantia Uitsig at the bottom of this list with an asterisk: the land is pre-1776, but the continuous winemaking is not. We make the case for inclusion because it is part of the original Constantia title, planted on the same soils as its three older siblings, and because the contrast between its contemporary glass cellar and Groot Constantia's 1791 stone Cloete Cellar is itself a statement about how Cape winemaking has evolved across 340 years. The signature wines are a Sauvignon Blanc and a Chardonnay; the La Colombe restaurant on the property is currently rated in Tripadvisor's top 20 restaurants in the world.