The 14 Best Places to Drink and Do in Cape Town

The wine that put Constantia on the map centuries ago is a sweet dessert wine, and Klein Constantia is the estate that brought it back from near-extinction. Set in the Constantia hills with Table Mountain overhead and ocean on the horizon, it's a working vineyard you can explore by bike or 4x4, taste through in a room framed by jacaranda trees, or linger over in the fine-dining bistro. Ranked sixth on the World's 50 Best Vineyards list.

1. The 50 #6 · The World's 50 Best Vineyards

A colony of African penguins has claimed this beach near Simon's Town, and they have absolutely no interest in sharing the agenda. The giant granite boulders carve the shoreline into sheltered coves where the water runs warmer than anywhere else on the Atlantic side of Cape Town, making it a rare spot where swimming is actually inviting. Named among the World's 50 Best Beaches, it draws everyone from wildlife researchers to families who just want a penguin in their holiday photos.

1. World's 50 Beaches #45 · The World's 50 Best Beaches

A cocktail bar that earns its mystique: the address is withheld, the website offers little but a booking link, and you'll need a password before you find the place tucked inside a Victorian warehouse in central Cape Town. The bartenders dress the period, every vintage detail follows through, and the cocktail list is inventive enough to justify the ceremony. A Discovery from The 50 Bar Awards. Other so-called speakeasies are taking notes.

1. The 50 The 50 Discovery
2. Difford's Guide Difford's Guide

1. The 50 The 50 Discovery
2. Difford's Guide Difford's Guide

1. The 50 The 50 Discovery
2. Difford's Guide Difford's Guide

1. The 50 The 50 Discovery
2. Spirited Awards 2026 · Regional Top 10 Honoree · Best International Bar Team – Middle East & Africa
3. Spirited Awards 2026 · Regional Top 10 Honoree · Best International Cocktail Bar – Middle East & Africa

1. The 50 The 50 Discovery
2. Spirited Awards 2026 · Regional Top 10 Honoree · Best International Cocktail Bar – Middle East & Africa

The sweet Constantia wines here once reached Napoleon's table on St. Helena, which gives you a sense of how far this estate's reputation traveled. Groot Constantia is Cape Town's oldest wine estate, set against the eastern slopes of Table Mountain with views out toward False Bay. The self-guided visitors route takes in Cape Dutch architecture, a wine and cultural history museum, and cellars where the revived Grand Constance dessert wine is still made.

1. The 50 The 50 Discovery

1. Spirited Awards 2026 · Regional Top 10 Honoree · Best New International Cocktail Bar – Middle East & Africa

1. The 50 The 50 Discovery

1. The 50 The 50 Discovery

A three-floor cocktail bar where vintage sports memorabilia covers the walls in tribute to a former owner who ran a speakeasy in the basement and apparently collected both pills and pennants. The balcony overlooking Signal Hill earns its reputation. Classics and barrel-aged options anchor the drinks list, while the signature side leans into housemade ingredients and stranger flavor pairings for anyone who wants the bar to do the thinking.

1. The 50 The 50 Discovery

The building was a slave prison before it became a cocktail bar, which gives Heritage Square's best-kept secret a weight that no amount of exposed brick could manufacture on its own. The Drinkery leans into the history with contemporary art on the walls, a chessboard for lingering, and a living-room vibe that makes ordering a third drink feel perfectly reasonable. The cocktail list skews adventurous, with port and absinthe sharing a glass without apology.

1. The 50 The 50 Discovery

A gin bar tucked inside a Mediterranean-style courtyard, reached through a cafe that gives nothing away. Once inside, the theme is South African gin, with over 70 local bottles on the shelves and a signature G&T list drawn from the building's former life as a morgue, which is either a gimmick or a perfectly reasonable way to name a cocktail, depending on your disposition. No speakeasy cosplay, just a lot of very specific botanical choices.

1. The 50 The 50 Discovery