The picturesque Riebeek Valley hosts some of the oldest estates on the route.   
Nestled against the Kasteelberg (Castle Mountains), the charming villages of Riebeek West and Riebeek Kasteel promise to entice visitors with its wineries, museums, arts and crafts and fabulous eateries.  The area is also well-known for its prolific olive production and most of the wineries offer a wide range of olive products for tasting.

Allesverloren Estate dates back to 1704 and passed into the hands of the Malan family in 1872. Allesverloren is known for its Port, as well as its range of excellent red wines namely Cabernet Sauvignon, Shiraz and oak-aged Tinta Barocca and Touriga Nacional. The restaurant, The Pleasant Pheasant@Allesverloren, is open for lunch daily and for dinner from Thursday to Sunday. On 1 December 2006 a Function Centre will open on the Estate.

Belonging to the Brink family Pulpit Rock Winery in Riebeek-West opened their doors in 2004. The cellar boasts beautiful brand-new tasting facilities and a function area with stunning views of the valley. Wines are bottled under the labels Pulpit Rock and Cape Haven.

Riebeek Cellars resides at the foot of the Kasteelberg mountain. The cellar was established in 1941 and prides themselves in their excellent quality wine ranges, which includes the Riebeek Cellars and A Few Good Men labels. Group visits are encouraged and cellar tours can be arranged by prior booking.

Kloovenburg Wine & Olive Estate stretches along the lower contours of Kasteelberg. The best red grape cultivars are selected for Kloovenburg’s exclusive red wines, Shiraz, Merlot and Cabernet Sauvignon. Grapes from low-yield vines with concentrated fruit flavours go into the crisp, barrel-fermented Chardonnay, which is also part of the selection on offer.

Het Vlock Casteel is a family run estate that produces wine, olives and fruit and also offers vineyard and farm tours. A visit to the trade mark "castle" is well worth the effort to taste and purchase the many products on offer - besides the Merlot, Shiraz & Cabernet Sauvignon, a variety of olive and fruit products are sold under the Het Vlock Casteel label.

Meerhof Cellar invites you to enjoy the views of rolling hills and Table Mountain on the one side and the beautiful Riebeek Valley on the other. The cellar focuses on premium red wine cultivars viz. Shiraz, Cabernet Sauvignon, Merlot and Pinotage with Chardonnay as white cultivar. Apart from excellent wines, Meerhof also provide meals in its intimate restaurant. Bookings are essential for the restaurant.

Riebeeck Olive Boutique offers visitors the opportunity to taste not only olives and olive oil; they can also taste a perfectly paired wine.  With each of their olive products they now offer the visitor the chance to taste and buy a wine that is perfectly matched.