Decades of cultural and economic evolution have radically transformed Sydney’s nightlife. In the 1930s, it was all about grand ballrooms like the Trocadero on George Street, pulsing with big jazz bands and swing orchestras. Post-war, the city turned to cabaret and the thriving arts scene of Kings Cross — Sydney’s nocturnal epicentre until the ’70s, where the glamour of neon met the shadowy dealings of figures like Abe Saffron, a.k.a. Mr. Sin.
The ’80s and ’90s ushered in a more underground current, as the rise of club culture and epic Rat Parties celebrated freedom, inclusivity, and LGBTQ+ expression on a mass scale. Then came the darkest stretch: from 2014 to 2020, New South Wales’ lockout laws imposed heavy curfews that nearly silenced the city’s after-hours spirit. But since their repeal, Sydney has been reborn — culturally vibrant, socially aware, and driven by a new idea of nightlife that favours memorable experiences and mindful drinking.
Maybe Sammy, Italian hospitality in Sydney
At the forefront of this renaissance is the Maybe Group, led by Stefano Catino and Vincenzo Lombardo, who’ve brought a distinct warmth — and a hint of Italian flair — to the far side of the globe. Their flagship, Maybe Sammy, calls itself a “hotel cocktail bar without a hotel”, a place where time slips away to the rhythm of live DJ sets, contemporary drinks, and the playful choreography of pink-jacketed staff. Guests are greeted with a Martini mixed tableside from a sleek trolley, before diving into a menu conceived as an elegant board game: The Grand Maybe Sammy Hotel. Among the signatures, Aromatherapy offers an ode to relaxation, blending whisky, French vermouth, almond and pear.
A Plunge into Mexico With El Primo Sanchez
Agave lovers have two distinct paths to follow. El Primo Sanchez channels Mexican vibrancy with a drink list by Eduardo Conde, offering bright twists like the mandarin-kissed Sanchez Paloma and the shiso-scented Mexican Mule. There’s a karaoke room with a “Press for Tequila” button for vocal courage, and La Prima — a hidden space that spirits you straight to Oaxaca.
CantinaOk!: Sydney’s Hidden Gem
For something grittier, there’s CantinaOk!, a micro-cantina down a back alley with no chairs, no frills, and a lot of soul. Here, mezcal is flown in straight from Mexico, Margaritas are served over hand-shaved ice, and the cocktail of the day is sketched live onto your coaster. What looks casual is in fact a love letter to craft.
Dean & Nancy on 22: an Exclusive View of Sydney
Dreamier moods await at Dean & Nancy on 22, a rooftop hideaway in the heart of the city. Its “World of Dreams” menu is a multi-sensory voyage: Ayahuasca Daisy arrives with 3D glasses to unlock psychedelic reveries through tequila, apricot tea, and amaro, while the Velvet Venom Milk Punch is tucked inside a sea urchin-shaped glass, layering rum, matcha, and vanilla into a lush, velvety sip.
From the Sartorial Charm of Tailor Room to the Underground Nightlife of Little Cooler
In historic The Rocks, Tailor Room is a new standout. Just 24 square metres, yet executed with surgical precision and a tailor’s touch. Each cocktail in the Textures collection is inspired by fabric: Silk is light and sparkling, with gin, geranium, and sandalwood evoking softness on the palate, while Denim, deep blue and bold, matches ginger with bergamot.
To close out the night, Little Cooler keeps the lights on until 2 a.m. in a basement on Clarence Street. A neon-drenched ode to American rock’n’roll dive bars with a ’90s look by Steel & Stitch, it’s already a hit with the bar world — grunge spirit, creative cocktails, and a killer playlist included. Just one more reason Sydney’s elegant, ever surprising bar scene is worth staying up for.
The article first appeared on Coqtail – for fine drinkers. Order your copy here
