A girls’ night out in Cape Town turns into a lively cocktail hop, moving through three very different bars. Between new discoveries, classic favourites and the city’s easy nighttime energy, each stop serves its own story, and its own surprise.
Rumour has it that every great story starts with a night out in Cape Town. I can’t confirm this, but I can share one of my best nights in Cape Town. Let me set the scene: three curious young women headed out on an ordinary Friday in January, hoping to avoid another Long Street misadventure. My friends and I had been keen to try the famed Art of Duplicity, a speakeasy in a quiet corner of Woodstock. After booking, we aimed to make the most of our night by also visiting two fascinating bars at the V&A Waterfront and the Cape Grace Hotel.
Some of my favourite things about Cape Town summers are the late sunsets and the joy they bring to the city. The 7 p.m. sunsets, strolls along the promenade, and spontaneous after-work drinks make everything feel colourful. Breaking with form, we set a dress code and chose 'Santorini Chic': fun, elaborate night items paired with relaxed, flowy pieces. It gave us a dressed-to-the-nines-but-not-really vibe. At the time, I lived in Stellenbosch, so to make the most of our night, I spent the weekend in Cape Town and booked a cosy bachelor flat in Woodstock.
Woodstock has an artistic, industrial (almost eclectic) ambience. Colourful Dutch-style homes contrast with the modern industrial high-rise buildings that sprawl across the neighbourhood. My skilful cab driver, Uncle Ernie, miraculously manoeuvred through the traffic and brought me to my first stop with time to spare. Though his name was Ernest, he insisted I call him Uncle Ernie and even offered me gum he had stashed away in the centre console. Despite all the warnings of crime and chaos in Cape Town, clear reminders of the kindness of its people are always welcome.
The Silo Hotel occupies six floors above Zeitz MOCAA, the world's largest museum dedicated to contemporary African art. Naturally, the hotel blends unique architecture and contemporary artistic flair in its presentation of African luxury. As I walked into the lobby, I saw some of the most intriguing artworks I'd ever seen. I immediately took out my phone to take photos—an act that felt like sacrilege. I exchanged glances with one of the doormen, who noticed my enthusiasm, and we both giggled. He walked over and asked if I needed assistance. I told him I was looking for the rooftop bar. He introduced himself as Nathanzo and escorted me to the bar. “This building used to be a silo, which is where the hotel gets its name from,” Nathanzo said as we walked to the rooftop.
I’d visited Zeitz MOCAA a few times before, but I’d always assumed the building was designed that way for aesthetic purposes. That the hotel and museum have leaned into the building's history is rather impressive to me. When I arrived at the bar, I tipped Nathanzo and settled into a seat at a table, waiting for my friends to arrive. I decided to sneak in a pre-drink before their arrival and asked the waitress to bring me her favourite drink. She returned with The Silo Signature, a gin and Chenin Blanc-based cocktail featuring egg white and other accoutrements, essentially a pseudo-whisky sour without the whisky. It was frothy, tart, and dangerously easy to drink. The bar features a spacious swimming pool and offers a beautiful view of the city’s skyline, with Table Mountain prominently visible. I would have definitely taken a dip in the pool had I carried my swimsuit, but I had to admire it from afar instead.
Gugu and Toni arrived fifteen minutes later, one after the other, just as I was in the middle of my cocktail. “Someone is really greedy for a good time," Gugu said, and we all burst out laughing. We'd arrived just after 5 p.m., giving us a solid hour before the bar closed at 6 p.m. We ordered a few tapas to share, and they ordered a whisky sour and a margarita each. It was a slow evening, and the tapas and drinks were lovely. We paid for our items and made our way to Bascule Bar at the Cape Grace Hotel, which is a short drive from The Silo Hotel.
The Cape Grace Hotel lobby had a classic V&A Waterfront aesthetic, characterised by white walls and a minimalist vibe. This introduction was a stark contrast to the overtly flamboyant Bascule Bar, which overlooks the marina. Bascule is the kind of establishment you visit if you’re looking for an elegant evening of fun. The bar is both a cocktail and whisky bar, boasting an extensive collection of over 500 whiskies and wines. When we arrived at the bar, I could tell from the music that the party was slowly brewing. The décor was a mix of Wes Anderson-meets-quasi-tropical Art Deco. At a nearby table, a group was celebrating a birthday, adding to the liveliness. When our waitress handed us a beautifully designed vintage-style cocktail menu, we opted for a cocktail tasting instead of a wine tasting. I decided on the Black Rhino Bloom, and the girls chose the Port to Port. The presentation of the drinks was an experience in itself; mine was in a brown paper bag, and the others were served at the table. As we worked on our second round of drinks, the birthday party began singing the birthday song, and in a feat of liquid courage, we joined in; eventually, the whole bar chimed in. It was at this point that we decided to make our exit, lest we end up at their after-party.
Divulging the details of my experience at Art of Duplicity seems sinful, but I’ll do it anyway because I promised a good story. Ranked one of the best bars in the world by numerous publications, Art of Duplicity is a speakeasy-style bar. To gain access, one must first make a reservation on their website. If (notice I said 'if', and not 'when') you secure a reservation, you will be given a password that you must repeat at the door to gain entrance, along with a set of clues that will lead you to the bar’s location. This scavenger hunt was comical, made even funnier by the fact that my friends and I were tipsy at this point. Pro tip from our slightly tipsy scavenger hunt: save the clues on your phone before you start pre-drinking! After trying to lead us astray, the doorman eventually let us in. Visitors beware: you must dress the part to be admitted.
Our outfits passed the vibe check (a notch above smart casual and definitely worth the effort), and we were welcomed inside. Art of Duplicity feels like a time capsule of the early 20th century, complete with vintage posters, dim lighting, and bartenders dressed as Victorian chimney sweeps. At one point, our bartender, complete with his vintage costume, performed an elaborate routine while mixing our drinks, full of theatrical flourishes and knowing winks. The girls continued with whisky-based beverages, and I opted for gin-based drinks, asking the waiter to bring us the recommended drinks in that order. He returned with The Gilded Pear for me (a gin concoction that tasted like autumn in a glass, all spiced pear and botanical notes) and The Flamin' Injuns and Jolly Jumper for Toni and Gugu. Each drink was as strong as it was delicious.
We decided on only two drinks each, and lingered for another two hours before calling it a night and grabbing some fast food on our way home. I vaguely remember wobbling to my room, a quick shower, and falling asleep immediately. With great company, the night was one of the best I’ve ever had in Cape Town—great drinks, an ambient atmosphere, and, most importantly, no ear-splitting hangover.
