đź“… Open Today: Crawl likely open on Sundays
Join us for a sophisticated evening in Woollahra on our Cocktail Crawl. Explore 3 top venues including I Maccheroni, Italian Osteria, B. Lucky & Sons Entertainment Quarter, and Royal Hotel Paddington. Indulge in delicious drinks and upscale pub grub while experiencing the vibrant nightlife of this elegant neighborhood. Get ready to sip, savor, and socialize in style!
Last updated: May 2025
Kick off your night in Woollahra with a cocktail crawl that pulses with energy and flavor. This three-stop journey starts where the rich aromas of fresh pasta and fine wine set an intimate yet lively tone. Next, amp up the fun as you step into a vibrant venue blending inventive cocktails with timeless arcade games, sparking laughter and friendly competition. Finally, wrap the night in style at a swanky multi-level pub where expertly crafted drinks meet a sophisticated atmosphere, perfect for raising a glass to an adventurous evening well spent. This crawl isn’t just about drinks — it’s a social thrill ride through Woollahra’s most dynamic hotspots.
Launch your crawl immersed in vibrant Italian flavors and warm hospitality, where fresh pasta and handpicked wines ignite the night’s excitement with genuine charm and culinary delight.
The next stop is a lively 15-minute stroll that transitions you from intimate Italian elegance to the buzzing heart of playful cocktail creativity.
Inject a burst of energy into your evening at this spirited arcade bar, where innovative cocktails and retro games turn every sip into a shared adventure of fun and friendly rivalry.
The next stop is a quick 10-minute walk that shifts the vibe from playful escapades to a polished, upscale pub scene with a sophisticated edge.
Conclude your crawl in style at this multi-level venue where expertly crafted cocktails and refined pub fare create an electric yet elegant atmosphere, perfect for savoring the night’s grand finale.
The crawl concludes here, offering a luxurious spot to toast to an unforgettable Woollahra night.
This Woollahra cocktail crawl offers a dynamic night out packed with flavor, fun, and flair. Whether you’re indulging in Italian classics, battling it out over arcade games, or unwinding in a chic pub lounge, each stop fuels your adventure and sparks new connections. Ready to explore Woollahra’s spirited side? Grab your crew and let the cocktails—and good times—flow.
Crawl Map