The Coolest Streets To Visit In Cape Town

By Shitika Anand, Social Media Manager, Unsettled

Raise your hands if you agree: a city is best explored on foot.

Whether it’s with a hike up Lion’s Head, or a wander down a secret alleyways on Bree Street to find artisanal beer, Cape Town is best explored in your hipster-approved sneakers.

Every shop front and cobbled path is so picturesque, you’d think Cape Town’s streets were curated by an Instagram influencer (it’s not).

If you want to get the most out of your experience in Cape Town, follow our Capetonian-approved itinerary of the coolest blocks in this town. Ready?

Bree Street

This long stretch of road runs through the heart of the Cape Town’s City Bowl, and is considered a hipster’s paradise. What used to be just a few shops here and a few organic cafe’s there has now transformed into a hub for local artists and quirky-cool ceramic shops. A stroll down here will have you brushing shoulders with the movers and shakers of Cape Town who are taking handcrafted jewellery and one-of-a-kind textiles to another level.

Bree Street is buzzing on most nights of the week, but it really comes alive on the first Thursday of every month, where art galleries, shops, and restaurants stay open later than usual. “First Thursdays” is a public event where visitors are encouraged to tour the street on foot. It’s a great time to mingle with locals and get to know the cultural heartbeat of the city.

You can also wander up to the Bo-Kaap, where the cobbled streets and neon-hued houses have a story to tell…

Kloof Street

The fashion crowd in Cape Town chooses Kloof Street for its local hangs on a mundane Tuesday night. This seemingly long stretch of shops, restaurants and art galleries begins from where Long Street ends and goes up all the way until the affluent suburb of Higgovale in Upper Cape Town (not to be compared to Upper East Side!).

Fashion boutiques, contemporary art galleries, interior design shops and cold-pressed juiceries embellish either sides of this street, and Capetonians just can’t get enough of it. If fashion trends aren’t your thing, hike up the street to The Bombay Bicycle Club, this city’s wackiest venue where you can run a Unsettled workshop or dance on tabletops until dawn.

Main Road in Green Point

If you’re visiting Cape Town for the first time and want to experience the city like a local, Green Point needs to be your destination. What Soho is to London, Green Point is to Cape Town.

The bustling nightlife poses a great ambience for party seekers, meanwhile the food joints on this street will savour almost every palate. The main road in Green Point is dotted with some of the best restaurant in town, right from authentic Italian at Giovanni’s to unlimited tacos at El Burro. The Banting Kitchen serves some of the Cape Town’s best braised pork belly with sweet potato mash, and Cubana Latino Café is where you want to end your night.

Green Point is also located along the V&A Waterfront, making it an ideal spot for bicyclers. You can rent Up Cycle all along the Sea Point Promenade.

Victoria Street in Camps Bay

With the sea kissing our feet and the mountains providing a backdrop, there’s a solid reason why Camps Bay was chosen as the basecamp for our Unsettled October family. This trendy suburb is only seven minutes from town centre, and one of Cape Town’s most scenic spots.

If you like the look of plush suburbs and like day dreaming about expensive waterfront-facing condos, head down to Victoria Street in Camps Bay. Not only will every house become Instagram-friendly (careful when taking photos!), but you’ll also treat your eyes to some inspiring architecture.

However, an expensive neighbourhood also equals expensive palate. The restaurants on this street are fine-dine heaven, all sitting on the lips of the Atlantic Ocean. Need some cool spots for a meal? Head to Bungalow Restaurant & Lounge, Azure Restaurant or Codfather Seafood and Sushi.

Long Street

Most city guides will still count this as the coolest street in the city, however, our very dedicated local Unsettled staff tell us how the gilt of Long Street is slowly fading. Being one of the oldest commercial streets in Cape Town, this street instantly has everything for everyone. In the late 1800s, Long Street was the longest street in Cape Town, stretching from the harbor all the way to Tamboerskloof in the upper part of the city.

However it’s had its niche stripped off in the last few years (especially with other cooler streets picking up their game). Irrespective, pay a visit to this oldie and she’ll show you a good time, if not the best.