đź“… Open Today: Crawl likely not fully open on Sundays
Experience the vibrant nightlife of Darlinghurst with our Hotel Bar Hop! Visit 3 venues including Love, Tilly Devine, Castlereagh Boutique Hotel, Ascend Hotel Collection, and Bitter Phew. Enjoy funky, cosy bars with eclectic furniture, classy upscale wine bars, and laid-back watering holes with craft beers. It's the perfect night out for a mix of ambiance and drinks!
Last updated: May 2025
169 Castlereagh St, Sydney NSW 2000, Australia
~1011m walk to next stop
Dive into Darlinghurst’s dynamic bar scene with this electrifying 3-stop hotel bar crawl designed for adventurous night owls craving variety and vibrant social energy. Kick off your evening at Love, Tilly Devine — a sultry wine bar bursting with eclectic charm and an adventurous approach to natural and orange wines paired perfectly with shareable Italian bites. Next, ascend to the refined atmosphere of Castlereagh Boutique Hotel, where timeless Art Deco elegance blends seamlessly with a food-centric menu and premium drinks, inviting you to elevate your experience in a sophisticated yet welcoming setting. Finally, round out the night at Bitter Phew, a craft beer gem where rustic wooden beams and an ever-evolving tap list fuel lively conversations and spirited discoveries. This crawl’s energy unfolds from intimate and stylish wine exploration, through polished hotel bar sophistication, culminating in a buzzing craft beer haven—guaranteeing a night packed with excitement, great drinks, and unforgettable social adventures.
Launch your night at Love, Tilly Devine, where a funky, eclectic setting invites you to explore an adventurous wine list focused on natural and orange varieties. Its intimate vibe and Italian-inspired plates set an energetic yet approachable tone, perfect for sparking great conversations.
The next stop is a short, lively stroll towards Sydney’s CBD, transitioning the vibe from cozy wine bar to classic Art Deco sophistication.
Elevate your evening with a visit to the Castlereagh Boutique Hotel’s chic bar, where heritage-listed Art Deco style meets a food-focused menu and premium cocktails, balancing elegance with warmth and making it an essential link between laid-back sips and energetic craft beer discoveries.
The next stop is a quick walk back into the heart of Darlinghurst, shifting the scene from polished hotel bar cool to a spirited craft beer hangout.
Cap off your adventure at Bitter Phew, where exposed wooden beams and a vibrant, evolving craft beer selection create a lively atmosphere perfect for deepening connections and savoring new brews in one of Darlinghurst’s most inviting and buzzing spots.
The next stop is the conclusion of this crawl, leaving you perfectly placed to continue the night or head home with memories of a spirited Darlinghurst adventure.
This 3-stop Darlinghurst hotel bar crawl takes you on an unforgettable journey through Sydney’s vibrant nightlife spectrum — from eclectic wine treasures and refined hotel elegance to lively craft beer havens. Whether you’re meeting old friends or making new ones, each stop builds on the last, ensuring a night brimming with energy, flavor, and social spark. Ready to sip, savor, and socialize your way through Darlinghurst? Grab your crew and dive into this spirited adventure now!
Crawl Map