Initially we planned to take off from Cape Town for a few days to explore the Garden Route, with the idea to stay overnight at one of the many vineyard bed and breakfasts dotting the Cape Winelands region. Instead, those pesky sharks threw a wrench in our plans, but we still made the most of our time by doing a day trip to the Franschhoek and Stellenbosh wine regions directly from Cape Town. Later in the week we took advantage of beautiful weather to explore the Constantia wine region, and of course we couldn’t say goodbye without a pub crawl, so we drank our way down the infamous Bree & Long Streets to see how the Cape Town locals spend their evenings.


We started our wine tour with a recommendation from our AirBnB host in the Franschhoek region. Franschhoek, an easy and scenic 40 minute drive from Cape Town, was settled in 1685 by French Huguenots. The region boasts many accolades for its food, wine and rustic beauty nestled against a mountainous backdrop.

Cape Winelands - Chamonix

We selected Chamonix vineyard as our first stop on the tour, which may have been a mistake considering I judged every subsequent vineyard to it, and none quite lived up to its charm. We arrived on a brisk fall day to this beautiful mountain village, where we settled comfortably into the tasting room, a converted 18th century blacksmith’s cottage. Typical as it was low season we were the only patrons around, so we were cordially greeted by Louisa, the sweet sommelier, who walked us through each of their exquisite wines. We shared lively conversation with Louisa, and after 5 hefty tastes we purchased their “sassy” Pinot noir to take home with us.

If we were to continue safely on our tour we needed a nice meal, so Louisa suggested a visit to Boschendal farm & vineyard. After small and quaint Chamonix, we were stunned by the picturesque beauty of this sprawling estate. Boschendal is one of the oldest farms in South Africa, dating back to 1685. Located in the Drakenstein Valley, the stunning mountainous backdrop is the perfect complement to the architectural beauty of the estate. The central feature is the manor house, a national monument which has been restored and furnished to reflect its original design. The beautifully manicured courtyard outside the manor features beautiful aged trees, a deli in the restored wagon house, gardens, picnic spaces and art installations. The Rhone homestead at the end of the square is open during the winter for Sunday lunch, and the flagship Werf restaurant is located between the homestead and the manor house, quite aptly in the restored original cellar house.

Cape Winelands - Boschendal

We were seated in the bright Werf dining room adjacent to the huge fireplace, with an excellent view of the farm and surrounding mountains. We selected a local favorite varietal, Chardonnay Pinot-Noir, to enjoy with our meal. The focus at Werf is on local, seasonal, sustainable and ethically-sourced foods. We feasted on house-made fermented breads, fresh produce sourced from the farm and local seafood classics. Each dish was beautifully balanced and the artful presentation gave our lunch a very fancy feel. Highlights included an octopus ravioli with sea lettuce and farmyard duck with black garlic jus. I personally enjoyed the horse mackerel accompanied by pickled mussel.


After our lunch we had time for one more tasting, so we ventured on to the neighboring Stellenbosch region. This region, equally rich is history, boasts more global notoriety than sleepy Franschhoek.

Cape Winelands - Tokara

The atmosphere and aesthetic at the Tokara estate provides a stark contrast to the rustic charm of Chamonix or elegant heritage of Boschendal. The winery and restaurant have a modern industrial feel, featuring artistic design elements throughout the property. Modernism goes well beyond the design at Tokara. The winery uses cutting-edge technology for vineyard analysis and wine production. The estate also produces excellent olives and olive oils, also available for tasting.

Cape Winelands - Tokara


The Constantia wine region is much smaller than Franschhoek or Stellenbosch, but its proximity to Cape Town makes it a wonderful option for anyone with only a few days in the Cape to get a taste of true South African wine culture. Groot Constantia is by far the most recognized vineyard in the region, heralded as the first wine farm in South Africa. It was established in 1685 by Commander Simon van der Stel of the Dutch East India Company, and today the original manor house serves as one of the most iconic examples of Dutch Renaissance architecture in the Cape.

Cape Winelands - Groot Constantia

The long viticulture history at Groot Constantia has produced exceptional wines heralded around the world. Visitors could easily spend the better part of the day touring the vineyards and museums, perusing the art collection available for sale and experiencing the wine and chocolate tastings. Many visitors opt to purchase bottles on site and spend the afternoon picnicking on the estate or gathering around the large tables in the tasting room for camaraderie with friends. Bus tours are available from Cape Town, which make it an excellent option for a boozy afternoon.

Long Street and Bree Street

For a night on the town, Long Street and Bree Street are the perfect places to enact a pub crawl. During the day, Long Street boasts a number of boutiques, antiques shops and bookstores in its Victorian-era buildings. At night the street comes alive with bohemian-hipster bars and nightclubs.

Bree Street Pub Crawl

Bree Street is newer to the restaurant and bar scene, giving it a more relaxed and local feel than Long Street. It also boasts charming boutiques and specialties stores, great to peruse for unique gifts and souvenirs. Consider picking up a cigar from Sturk’s Tobacconists, a tiny storefront continually in business since 1793. We enjoyed an afternoon craft beer and pickled string beans at Clarke’s Bar and Dining Room, one of Bree Street’s many good eateries. One of our favorite spots during our nighttime pub crawl was Orphanage Cocktail Emporium, a speakeasy-inspired haven for sophisticated mixology, which donates R15 to a children’s home with the purchase of the ‘More Tea, Vicar’ rooibos infused cocktail. Another great option is Mother’s Ruin Gin Bar, which offers 82 artisanal and small batch gins for your not-so-typical G&T.

Sojourn Information

Franschhoek – Everything you need to know about the region.

Chamonix – Tastings available daily from 9:30-17:00 from R35+.

Boschendal – Tastings available daily from 9:00-16:30. Chocolate wine tasting R70.  Vineyard tours available November-April, cellar tours available daily.

Stellenbosch – Official wine route.

Tokara – Complimentary wine and olive tastings available daily, R10 for brandy.

Groot Constantia – Tastings available daily from 9:00-18:00, except Good Friday and Christmas, for R45+. Cellar tours available.

Long Street – Bar guide.

Bree Street – Restaurant guide.

Sturk’s Tobacconists – South Africa’s oldest family-run business.

Orphanage Cocktail Emporium – 227 Bree St, Cape Town City Centre, Cape Town, 8000, South Africa

Mother’s Ruin Gin Bar – 219 Bree St, Cape Town, 8000, South Africa

Clarke’s Bar and Dining Room – 133 Bree St, Cape Town City Centre, Cape Town, 8001, South Africa

Boozy Cape Town: Self-Guided Wine Tours and Pub Crawl

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