The Caterpillar Club

Down a Pitt Street stairwell—straight into a moody, 70s-glam fever dream. The Caterpillar Club is that dimly lit CBD basement where the city's hospo crowd goes to decompress. A sprawling bar stacked with wax. Deep, dark corners. Hidden tiki nooks for late-night mischief. Sydney cocktail purists consistently point to their razor-sharp dirty martinis and impeccably balanced negronis, especially when the 4–6pm happy hour hits. The energy? Pure, unadulterated vinyl-spun magnetism. Pair a round of drinks with their ridiculously juicy smoked burgers or buttermilk chicken. Sure, you'll navigate buzzing, elbow-to-elbow peak hours and premium price tags—but that’s just the cost of admission to the city's finest low-lit revelry.