đź“… Open Today: Crawl likely not fully open on Sundays
Get ready for a night of upscale fun in Woollahra with our Cocktail Crawl! We'll be hitting up 3 top venues including The Wine Library, B. Lucky & Sons Entertainment Quarter, and Royal Hotel Paddington. Indulge in a large wine list, share plates, games, and swanky cocktail lounge vibes. Don't miss out on this unforgettable evening out!
Last updated: May 2025
Kick off your night in Woollahra with a cocktail bar crawl that pulses with energy, flavor, and social flair. This carefully curated route launches you into an inviting world of global wines and shareable plates at The Wine Library, setting the stage with approachable elegance and vibrant conversation. Next, unleash your playful side at B. Lucky & Sons Entertainment Quarter, where inventive cocktails meet classic arcade games, crafting an atmosphere that’s as spirited as it is fun. Wrapping up the adventure, the Royal Hotel Paddington elevates the evening with its swanky multilevel spaces—sip expertly crafted cocktails amid polished wood interiors or catch the buzz in the smart sports bar. Together, these stops create a dynamic progression from warm sophistication through lively playfulness to stylish nightcap energy, making this crawl a must for cocktail adventurers craving excitement and variety in Woollahra.
As the perfect launching point, The Wine Library invites you into a cozy yet vibrant setting where globally inspired wines and share plates spark great conversation and set an elegant tone for the night ahead.
The next stop is a brisk and energizing walk that shifts the vibe from refined wine sophistication to playful cocktail creativity at B. Lucky & Sons.
This stop injects playful energy with inventive boozy bubble teas and classic arcade games, turning the crawl into an interactive adventure where fun meets craft cocktails in a lively setting.
The next stop is a short stroll that elevates the mood further, guiding you to the chic and sophisticated ambiance of Royal Hotel Paddington’s cocktail lounge.
Ending on a high note, Royal Hotel Paddington offers a swanky, multilevel experience where expertly crafted cocktails and upscale pub fare meet a stylish crowd, perfect for capping off an adventurous night out.
The crawl concludes here, allowing you to soak in the lively, upscale vibe without rushing to another spot.
This Woollahra cocktail crawl delivers an invigorating blend of tastes, vibes, and experiences — from world-class wines and share plates to playful cocktails and stylish lounges. Whether you’re celebrating a special night or simply craving an adventurous evening with friends, these three stops stitch together a memorable journey through the heart of Sydney’s cocktail culture. Ready to sip, play, and savor your way through Woollahra? Gather your crew and let the good times roll!
Crawl Map