22 Best Sights in Stellenbosch, The Western Cape and Winelands

At the end of Stellenbosch Kloof Road, this meticulous winery, flanked by the Bottelary hills, overlooks rolling vineyards and jagged mountains. Since the first vintage in 1993, the winery has established a formidable reputation. The Sauvignon Blanc makes for good summer drinking; the dense but fruity Nine Yards Chardonnay is extremely popular and has regulars stocking up on cases at a time. Another wine to try is the Cobblers Hill Bordeaux blend. The wine estate has an excellent restaurant, as well as a bakery where you can enjoy breakfast or a light lunch. Cellar tours are available by appointment; book at least a day ahead.

This is one of the oldest farms in the area, established in 1692 on the banks of the Eerste River. The farm produces excellent wines, which go from strength to strength. The flagships are the Frans K. Smit red and white blends, named after the winemaker. Also try the 21 Gables Chenin Blanc and Pinotage—both excellent. The farm's owners value biodiversity and arts and culture: their enormous art collection is displayed across the farm's public spaces, and their farm-grown produce is used in the restaurants. You can order a picnic and enjoy it on the banks of the river, or explore the farm on foot, by bike, or on a Segway tour. In addition to tastings, there is a chocolate and wine pairing and a hands-on blending experience. If you're traveling with the kids, visit Eagle Encounters, an on-site rehabilitation center for raptors. And if you just can't drag them away, there is a delightful hotel on-site complete with a kids' club, so you can sip while they play.

Perched on the crest of the Helshoogte Pass between Stellenbosch and Franschhoek, Tokara is the brainchild of banker G. T. Ferreira. For a city slicker with lots of money, he's done everything right and has scooped up awards. The Chardonnay was once voted one of the top 10 wines from around the world at the Chardonnay-du-Monde Awards. The flagship red, a blend of Cabernet Sauvignon, Merlot, Petit Verdot, and Malbec, is well worth taking home. Be on the lookout for the farm's limited-release Pinotage, taken from one block on the foothills of the Simonsberg. Tokara also has farms in the cooler Elgin and Hemel-en-Aarde regions, which means it can produce a stunning white wine blend (Sauvignon Blanc and Semillon) with plenty of complexity. The farm also presses its own premium olive oil, which you can taste and buy. The restaurant is a foodie's delight, and the Delicatessen is a perfect venue for a breakfast or light lunch. Kids love the free-form jungle gym—as good-looking as any contemporary sculpture—and the weaver's nest they can climb into that hangs in a huge oak.

Although the Ratcliffe family no longer runs the farm, the influence of founder Norma Ratcliffe is still evident. The first female winemaker in South Africa, Norma pioneered the way and is immortalized in the estate's popular Cabernet Sauvignon—The First Lady. Trilogy is a stylish and complex red made with Cabernet Franc, Cabernet Sauvignon, and Merlot. Another great red, the Three Cape Ladies, was named after the indomitable Ratcliffe women, and is a fabulous blend of Cabernet Sauvignon, Cabernet Franc, and Pinotage. The Cabernet Franc is undoubtedly one of the best wines made from this varietal in the Winelands. In summer there are kid-friendly vineyard tours that compare grape varietals to the Big Five animals from the comfort of a safari vehicle. Afterward, enjoy a decadent picnic on the lawn.

Some of Stellenbosch's most historic buildings face the Braak, the grassy town square. St. Mary's Church stands at the north end of the Braak. Built in 1852 as an Anglican church, it reflects the growing influence of the English in Stellenbosch. Across Bloem Street from St. Mary's is the Burgher House, built in 1797. Today it houses the offices of Historical Homes in South Africa but you can view the main rooms during office hours. Just across the road is the V.O.C. Kruithuis ("powder house"), the town's former arsenal dating back to 1777. There's a small fee to go inside and view the collection of guns, gunpowder holders, and cannons. At the southern end of the Braak is the Rhenish Mission Church, erected by the Missionary Society of Stellenbosch in 1823.

Stellenbosch's most historic avenue is oak-lined Dorp Street. Almost the entire street is a national monument, flanked by lovely restored homes from every period of the town's history. Look out for Voorgelegen at No. 116, a perfectly preserved Georgian home from the 19th century. Perhaps most interesting is La Gratitude at No. 95. This early 18th-century home was built in traditional Cape Dutch town-house style. The all-seeing eye of God molded on its gable was designed as a talisman to watch over the owner's property and keep him and his family safe from harm.

In the days when the Dutch East India Company stopped in Cape Town en route to the East, a ship would fire a cannon as it entered the harbor to let farmers know provisions were needed. A set of relay cannons on the hilltops would carry the message inland. One such cannon was on this farm, which was then called Kanonkop, Afrikaans for Cannon Hill. The beauty of Kanonkop today is not in its history or its buildings, but in its wine. Paul Sauer, a blend of about 70% Cabernet Sauvignon, 15% Merlot, and 15% Cabernet Franc, rakes in awards both in South Africa and internationally year after year. The Kanonkop Black Label Pinotage is an iconic wine produced in small quantities and sold only from the farm. There are no guided tours, but during harvest you can do a walkabout in the cellar to see the action. An added attraction is the art gallery featuring works from 50 leading South African artists. It's a wonderful selection of the totally traditional to the strikingly modern.

A visit to Meerlust, one of South Africa's most celebrated estates, provides an introduction to Cape history. In the same family for generations, the vineyard was bought by Johannes Albertus Myburgh in 1757. When Nicolaas Myburgh took over the reins in 1959, he began restoring the farm's Cape Dutch buildings. The entire complex was declared a national monument. Nico Myburgh did more than just renovate. In the '70s, conventional wisdom had it that Cabernet Sauvignon was king, but Nico went against the grain and opted for a Bordeaux-style blend, planting both Merlot and Cabernet Franc. The first wine, made in 1980 and released in 1983, was named Rubicon (an allusion to Julius Caesar) to symbolize the crossing of a significant barrier. Rubicon garners awards year after year and is rated as an international best seller. The estate makes only one white, a delicious, full-bodied Chardonnay. Meerlust's other wines—Cabernet Sauvignon, Pinot Noir, and Merlot—are also notably good. The low-key, relaxed tasting offers great value for money

A long and beautiful driveway emerges at Mulderbosch's tasting room and restaurant, both of which overlook a small lake. It's a relaxed and family-friendly spot, with a small jungle gym and unpretentious food like wood-fired pizzas and burgers. On the wine side, try the Steen op Hout Chenin Blanc, with notes of apple, peach, and pear, perfect for summer drinking. A large portion of the farm has been left to indigenous vegetation and wildlife, and they're attempting to restore endangered native renosterveld and fynbos vegetation.

Ancient oaks and a cellar that truly seems to be more concerned with the business of producing wine than with decor make this a refreshing change from the "prettier" wineries. It's a small estate, specializing in rich, earthy reds and full-bodied dessert wines. Muratie's port is an old favorite in the Cape, and the well-balanced Amber Forever is a fortified dessert wine with pleasing citrus notes to counter the sweetness. Worth looking out for are the Pinot Noirs, from some of the oldest vines of this cultivar in the Cape. The farm's flagship wine is the Ansela van der Caab, a red blend of Cabernet Sauvignon, Cabernet Franc, and Merlot, named after the freed slave who married the first owner of the farm, Laurens Campher, and helped set up the vineyards in the early 1700s. The Ronnie Melck Shiraz and Muratie Martin Melck Family Reserve Cabernet Sauvignon also come highly recommended. There are hiking trails, on-site cottages, and an unfussy restaurant serving steaks, salads, and a few South African specialties.

A long avenue of pines leads to this lovely estate, which traces its origins to 1692. The magnificent 1814 Cape Dutch manor house looks out across formal rose gardens to the Stellenbosch Valley and the Hottentots Holland Mountains. The Gewürztraminer is an off-dry, very elegant wine with rose-petal and spice aromas, and the Maria Noble Late Harvest (named after the feisty woman who built the manor house) is one of the best of its kind. The farm's Owl Post Pinotage is a single-vineyard wine matured in Hungarian oak, which makes it a funkier take on an old South African favorite. Look out for mocha, raspberry, and cherry flavors. Book ahead for the food-and-wine pairings, which include five bite-size servings paired with the estate wines—there's even a kids' version available. The restaurant is more casual than most found in wineries, serving salads, steak, burgers, and wood-fired pizza.

Redolent of tobacco, dried fish, and spices, this 19th-century-style general store is one of Stellenbosch's most popular landmarks. In addition to the usual Cape kitsch, Oom Samie sells some genuine South African produce, including witblits and mampoer, both Afrikaner versions of moonshine.

Among the established estates on Stellenbosch Kloof Road, Overgaauw definitely deserves a visit. You can admire the pretty Victorian tasting room while exploring the range of big red wines. David van Velden is the fourth-generation winemaker on the farm. Tradition hasn't stood in the way of innovation, however. In 1982 Overgaauw was the first South African estate to bottle a single-varietal Merlot, but it also experiments with other varietals, and you should, too. Try the wonderful Cape Vintage Port made with Portuguese varietals such as touriga, tintas, souzao, and cornifesto. The result is a richly balanced blend. The Tria Corda, a red blend, sells out faster than it can be released. The spicy, fruity Sylvaner is named for a grape of the same name. To date, Overgaauw is the only Cape estate to grow this varietal, which comes from the Alsace region of France, so it's definitely worth exploring.

One of the most impressive restoration projects ever undertaken in South Africa and a good example of what early Stellenbosch must have been like, this complex consists of an art center, which melds elements of English and Cape architecture; and a two-story building that is typically English. The complex is west of Die Braak, facing a large lawn. The Toy and Miniature Museum is based here (entrance R40) and houses a collection of scale dollhouses and antique toys, as well as a miniature model of the famous Blue Train.

This vast, modern building on the outskirts of town houses the art collection of Huberte Rupert, wife of local magnate Anton Rupert. The collection rotates but includes a wide selection of artistic styles spanning several centuries. There's a popular coffee shop inside the museum as well.

Nestled against the base of Helderberg Mountain, the peaceful Rust en Vrede winery is shaded by giant oaks and looks out over steep slopes of vines and roses. This comparatively small estate specializes entirely in reds and produces some of the very best in South Africa. In fact, Nelson Mandela chose this wine to be served at his Nobel Peace Prize dinner when he was president. Rust en Vrede Estate is the flagship wine, a blend of predominantly Cabernet Sauvignon, Syrah, and Merlot. Enjoy it now, but you can also put it away to mature in the bottle for another 10 years or more. Another weighty wine is the 1694 Classification (named after the year the farm was established), a blend of Syrah and Cabernet Sauvignon. The celebrated on-site restaurant is only open for dinner, but at lunchtime you can enjoy the winemaker's lunch—a set menu in the cellar. Choose between steak and salmon, accompanied by a generously poured glass of wine.

This estate may date back to 1682, but it's been brought thoroughly up to date with a state-of-the art winery and underground vaulted maturation rooms. It is known for red wines, particularly its 100% Cabernet Peter Barlow (named after the present owner's father), which is made from grapes from one lovely, well-tended vineyard. The Five Soldiers Chardonnay is delicious and also made from a single vineyard, which gives it its unique character. It's named for the five tall pine trees that stand guard on top of the hill above the Chardonnay grapes. Make time to explore the estate's beautiful gardens and labyrinth. These are open year-round but are best in summer. The lovely manor house gardens are open to the public one weekend a year in late October or early November. Book ahead for tastings if you're traveling in a group larger than four people.

Sitting in a sea of vines is this estate with tremendous views back toward Stellenbosch and the mountains. Simonsig has more than a dozen white and red wines of impressive range, both in terms of taste and price. But the winery is best known for its bubbles. Kaapse Vonkel was South Africa's first Méthode Cap Classique, and since 1971 this classic blend of Chardonnay, Pinot Noir, and a touch of Pinot Meunier has been among the best. For R205 you can try your hand at the sabrage—de-corking a bottle of bubbly with a sword—and then enjoy anything you don't spill. The Pinotage demonstrates how well this varietal fares with no wood aging, but the Red Hill Pinotage, from old bush vines, shows just how much good oaking can improve it. Cuvee restaurant offers seasonal, locally inspired dishes in a relaxed environment.

This museum includes four dwellings scattered within a two-block radius. Dating from different periods in Stellenbosch's history, the houses have been furnished to reflect changing lifestyles and tastes. The oldest is the very basic Schreuderhuis, built in 1709. The others date from 1789, 1803, and 1850.

On the slopes of the Simonsberg, just off the Helshoogte Pass, this is an excellent example of the exciting developments in the Cape Winelands since the early 1980s, when farmers began to eye land that hadn't traditionally been earmarked for vineyards. When Gyles and Barbara Webb started the farm in 1983, there was nothing here but very good soil and old fruit trees. It's a testament to their efforts that the winery has regularly won prizes for both its reds and whites ever since. To cap it all off, the view of the Groot Drakenstein Mountains from the tasting room is unforgettable. Ever the pioneers, the Webbs have also bought Sutherland, an old fruit farm in the Elgin area. The Sutherland wines, which can be tasted at Thelema, are wonderfully fragrant; look out for the Pinot Noir and Chardonnay.

Since starting in wine making in 1984, the Grier family has notched numerous successes. As John Platter, one of South Africa's foremost wine writers, once said, "Other winemakers might jog or work out in the gym; Jeff Grier gets all the exercise he needs stepping up to the podium for wine industry awards." The farm is famous for its range of Méthode Cap Classique sparkling wines. Try the Brut Natural, which is 100% Chardonnay and made using wild yeast; it has no added sulfur and no added sugar. The barrel-fermented Chenin Blanc is also very popular. Registered as a biodiversity farm, the winery produces chemical-free wines as much as possible; they use ducks to help control the snails and work to attract raptors to scare off the smaller birds that feast on the ripening grapes. There's no restaurant on-site, but they do offer cheese boards and a bubbly and nougat pairing if you book ahead. You can also combine a wine tasting with a drive through the 545-acre wildlife sanctuary (two hours, R350), where you'll see eland, gemsbok, giraffe, bush pig, and other wild animals. Booking is essential for the game drives.

Built in the style of a Tuscan villa, this modern winery lacks the centuries-old pedigree of many of its peers, but it more than makes up for this in the quality of its wine. The flagship is The Jem, a decadent and complex red blend featuring eight grape varietals. It wins accolades and awards on every release—you'll pay an extra R185 to taste it, but it's worth the splurge. The estate is also known for its chocolate and wine pairing experience (R150) which you can enjoy in the tree-lined courtyard of the winery. The on-site restaurant, Salt, offers unpretentious bistro fare for lunch. There are hikes and safari drives through the estate; advance bookings for these is essential.