đź“… Open Today: Crawl likely open on Fridays
Experience the best of Sydney’s skyline with our rooftop crawl featuring three amazing venues: The Cut Bar & Grill, Bar Ombré Rooftop, and Highlander Whisky Bar. Enjoy carefully sourced steaks and seafood in a refined space at The Cut, sip cocktails and dance to live music at Bar Ombré’s lively rooftop lounge, and unwind with upscale cocktails in a classy, old-world setting at Highlander Whisky Bar. Perfect for food lovers, night owls, and city explorers looking for a fun, elevated night out!
Last updated: July 2025
Kick off your night in Sydney’s iconic Rocks district, where The Cut Bar & Grill sets the stage with expertly grilled steaks and seafood served in a space that feels both historic and inviting. As your appetite for adventure grows, ascend to Bar Ombré Rooftop — a vibrant, music-fueled lounge that pairs panoramic city views with wood-fired pizzas and dynamic live performances. Finally, wrap up your rooftop journey at Highlander Whisky Bar, where old-world charm meets sophisticated mixology, offering a refined atmosphere to toast the night away. This compact crawl packs a powerful punch of flavor, energy, and style, designed for those craving an unforgettable urban night out.
Launch your crawl with The Cut Bar & Grill’s irresistible blend of hearty, flame-grilled flavors and a warm, brick-lined ambiance that grounds the night in Sydney’s historic charm.
The next stop is a short, invigorating stroll from The Rocks to Alfred Street, offering a chance to soak in the city’s evening buzz as you head towards a rooftop alive with music and views.
Amp up the excitement at Bar Ombré Rooftop, where the pulse of live DJs and vibrant city vistas meet shareable bites and handcrafted cocktails, setting a lively social scene.
The next stop is a brief urban walk along Macquarie Street, allowing the night’s energy to build as you approach a sophisticated hideaway steeped in old-world elegance.
Conclude your rooftop expedition at Highlander Whisky Bar, where plush surroundings and expertly mixed cocktails offer a polished finale to your Sydney night of spirited discovery.
The next stop is the end of the crawl—settle in and savor the refined atmosphere as you toast to a night well spent.
From the historic heart of The Rocks to skyline rooftops pulsing with energy and culminating in timeless sophistication, this Sydney rooftop bar crawl delivers a dynamic night packed with flavor, music, and style. Whether you’re celebrating a special occasion or simply seizing the city’s vibrant pulse, each stop promises a unique chapter in your urban adventure. Grab your crew, lace up your walking shoes, and elevate your nightlife with this carefully curated journey through Sydney’s best rooftop spots.
Crawl Map