đź“… Open Today: Crawl likely open on Sundays
Get ready for a night out in Woollahra with our pub crawl! Explore three fantastic venues including I Maccheroni, Italian Osteria, Paddington, Royal Hotel Paddington, and The Light Brigade. From rooftop views to classic pub fare, this crawl has it all. Grab your friends and let's have a night to remember!
Last updated: May 2025
Kick off your Woollahra night with a burst of Italian passion before moving into a refined pub atmosphere that balances sophistication and spirited energy. This three-stop pub crawl takes you from the heart of Italian osteria charm through a stylish cocktail lounge buzzing with excitement, ending on a high note at a rooftop terrace where classic pub eats meet panoramic city views. Whether you’re rallying a crew or sparking new connections, this crawl delivers a dynamic night packed with flavor, flair, and fun.
Start your evening at I Maccheroni where fresh pasta and bold Italian flavors set an irresistible tone. This food-centric osteria’s warm vibe and curated wine list fuel appetites and social buzz, making it the perfect launchpad for the night.
The next stop is a short, spirited stroll that shifts from cozy Italian charm to a sleek, multi-level pub experience.
Elevate the energy at Royal Hotel’s stylish cocktail lounge where expert mixology and upscale pub fare collide. The lively sports bar upstairs keeps the vibe buzzing with live action, perfect for sparking conversations and raising glasses.
The next stop is a quick, easy walk that transitions you from vibrant cocktail sophistication to a sprawling pub layout with an inviting rooftop.
Cap off your crawl at The Light Brigade, a four-level pub where classic dishes and a lively rooftop terrace combine for a spirited finale. The mix of relaxed lounge spaces and vibrant bar energy keeps the good times rolling under the open sky.
The crawl concludes here, where the open-air terrace invites lingering and celebrating the night’s adventure.
This Woollahra pub crawl blends bold flavors, chic settings, and rooftop thrills to craft a night that’s as social as it is spirited. Gather your crew, lace up your walking shoes, and dive into a dynamic journey where every stop amps up the fun and every sip sparks new stories. Ready to own the night? Woollahra awaits.
Crawl Map