Walk far enough up Kloof Street and you feel the city shifting beneath your feet. Not a geological shift— Table Mountain, perched overhead like a granite librarian reminding everyone to behave, usually handles that—but a human one. The closer you get to the Gardens district, the more the street begins to hum with the business of living: cafés exhaling the scent of good coffee, boutiques dressed like mini-museums, and restaurants that seem to multiply out of civic enthusiasm.

It’s here that Lee-Ann Chain, founder of Step Out Tours, begins many of her women-focused walks. She knows the street’s rhythms the way some people know a favourite novel: where to pause, where to listen, and where the stories grow loudest. With her, Kloof Street becomes less of a road and more of a conversation.

Among the addresses she loves to share, three landmarks—numbers 30, 103, and 117—hold stories that reach backwards into Cape Town’s past and outward into its culinary imagination.

30 Kloof Street: The Grand Old Dame

At number 30 stands a Victorian mansion with the unbothered grace of someone who’s seen everything and lived to smirk about it. It has been many things: a private home, a boarding house, and—if local whispers are to be believed—a brief, discreet brothel from an era when people were less forthcoming about such matters. The house has always known how to keep a secret.

Reborn in the early 2010s as Kloof Street House, it now feels like stepping into a novel you didn’t realise you were already enjoying. Rooms diverge like plot lines: some dusky and intimate, others bright with vintage flourish. A porch glows at dusk; a garden bar wakes up at night. On Sundays, jazz drifts through the outdoor space with the confidence of music that knows exactly how well it suits the architecture.

The menu leans brasserie—big-hearted, unfussy plates carried by cocktails that promise (and usually deliver) a very good evening. But the house’s real flavour is its memory: a heritage space that refuses to forget itself. You leave not only well fed but lightly seasoned with history.
W: Kloof Street House

A Chef Who Speaks in Landscapes

Before climbing farther up Kloof Street, Lee-Ann often slips her small groups into a detour—into the imagination of Chef Bertus Basson, whose restaurant Ongetem lives inside Canopy by Hilton, just off the main stretch.

Basson talks the way the land breathes. Raised in farm country, he speaks in vivid bursts—heritage cooking one moment, a Boland orchard glimpsed at dawn the next, a farm stall where he bought stone-ground maize because it “felt right.” Conversations with him are less dialogue than tailwinds; you draft behind his ideas and hope to catch each one.

His restaurants—Overture, Spek & Bone, Eike, Geuwels, Chorus—scatter across the Cape like compass points of South African flavour. Veld herbs, orchard fruits, stubbornly honest maize, free-range meats: this is his language. His plates feel like familiar memories rediscovered and suddenly shimmering.

He rides Harleys, too—loud ones, the kind that announce his arrival several postal codes away. It fits. Basson isn’t building an empire; he’s building pride—one dish, one conversation, one kilometre of roaring V-twin at a time.
W: Bertus Basson

103 Kloof Street: Rick’s Café Américain — A Casablanca Heartbeat

Halfway up the hill, Rick’s Café Américain sits like a well-travelled raconteur. Housed in a Victorian villa with the slightly rakish charm of someone who’s lived a few stories and polished them for retelling, Rick’s glows with Moroccan lanterns and worn wood. The décor nods to Casablanca without ever tripping into parody. You half expect someone to murmur, “Play it again,” though the cocktail list is usually more compelling than nostalgia.

From the rooftop terrace, Table Mountain leans in like a curious neighbour while diners share global tapas, Moroccan tagines, or unapologetically enormous burgers. The menu roams, but it roams with generosity— of portion, of flavour, of spirit.

Rick moves at an amiable, unhurried pace. Afternoons soften into evenings, the terrace warms, the bar’s encyclopaedic collection of spirits goes to work, and conversations loosen around the edges. Locals linger. Travellers feel instantly at home. Everyone leaves convinced that Cape Town has just revealed another layer of itself.
W: Rick’s Café

117 Kloof Street: A Conservatory of Taste and Texture

Continue uphill, and you’ll find Our Local, a restaurant that feels less like a venue and more like a greenhouse for the soul. Sunlight pours through its high glass roof with such generosity you half expect to grow a new leaf with breakfast. Plants spill everywhere—broad-leafed, viney, charmingly unruly—while mismatched furniture settles into corners like relics that wandered in and decided to stay.

Mornings arrive with gentle precision: citrus zest curling in the air, shakshuka murmuring on the stove, bread warming until it smells autobiographical. By afternoon, the flavours turn bolder—charred chicken with North African leanings, lemony pastas, lamb riblets that collapse at the fork.

At the centre of it all is Kerry, the manager, who conducts the space with the ease of someone tending a living artwork. Under her stewardship, Our Local doesn’t feel run; it feels grown. A place that unfolds slowly, like a plant turning toward the sun.
W: Our Local

The Street That Holds It All

Kloof Street is one of Cape Town’s essential connectors—not in the transport sense, but in the cultural one. It ties together eras, appetites, and imaginations. It carries Victorian ghosts, contemporary creativity, a chef on a growling Harley, garden bars, rooftop cocktails, and sunlight falling onto a plate of shakshuka. It’s a street where architecture and appetite sit comfortably in the same sentence. Where heritage houses become restaurants without abandoning their memories. Where locals and travellers mingle easily, drawn by the promise that something good—food, music, a conversation worth having—waits around the next
bend.

Walk it slowly. Or better yet, walk it with Lee-Ann, who guides women through the city with an eye for safety, story, and the small details that make a place feel like it’s speaking directly to you. Either way, let Kloof Street tell you its stories. It rewards curiosity the way Cape Town rewards those who look up at the mountain at least once a day: gently, generously, and with a sense of belonging.
W: Cape Tourism
W: Step Out Tours

Written by Cindy-Lou Dale for Luxuria Lifestyle International