đź“… Open Today: Crawl likely not fully open on Sundays
Join us for a delightful evening exploring the vibrant wine bar scene in Woolloomooloo. This classy and upscale crawl will take you to 7 venues, including Ovolo Woolloomooloo, De Vine Food & Wine, The Winery, Love, Tilly Devine, Dear Sainte Éloise, Chester White Cured Diner, and House Bar&Bistrot. Indulge in Refined European-style wine bars, Laneway gems with Modern Australian cuisine, and funky bars with eclectic wine menus. Each spot offers a unique experience, from classic Italian dishes to gourmet sourdough pizzas. Get ready to sip, savor, and socialize on this unforgettable wine bar crawl
Last updated: May 2025
Dive headfirst into Woolloomooloo’s vibrant wine scene with this 7-stop crawl designed for those who crave a dynamic blend of elegance, flavor, and social buzz. Launch your adventure where sleek modern design meets waterside energy at Ovolo Woolloomooloo, setting the tone for an evening steeped in style and spirited conversation. From there, journey through sophisticated European-inspired wine bars that pair impeccable vintages with expertly crafted dishes. Along the way, experience intimate laneway gems and eclectic venues offering everything from natural wines to classic Italian nibbles. Culminate your crawl in Potts Point’s culinary heart, where cozy, character-filled spots serve up gourmet pizzas and fresh seafood alongside curated Italian wines. Each stop elevates your night with a distinct vibe, flowing seamlessly from chic waterfront glamour to warm, lively neighbourhood favourites. Expect a social adventure filled with expertly poured wines, delectable bites, and the kind of atmosphere that sparks new connections and lasting memories.
Kick off the crawl at this stylish harbourfront hotel bar where modern design meets vibrant social energy, delivering a polished yet approachable setting to sip expertly crafted cocktails and wines right by the water’s edge.
The next stop is a quick, energizing walk into the heart of the city, inviting you to switch gears from waterfront chic to refined European wine culture.
Step into an upscale Italian-inspired haven where an exquisite wine list meets handmade pasta and classic dishes, amplifying the crawl’s momentum with rich flavors and warm sophistication.
The next stop is a short stroll towards a hidden laneway, shifting the vibe to a stylish yet bohemian wine bar experience.
Nestled in a lively Surry Hills laneway, this spot brings a fresh Australian twist with a carefully curated glass selection and vibrant Modern Australian plates, adding boho flair and a bustling garden atmosphere to the evening.
The next stop is an easy walk into Darlinghurst, where eclectic style and natural wines await to refresh the palate and elevate the energy.
This eclectic Darlinghurst gem infuses charm with a lively natural wine menu and Italian small plates, perfect for sharing and sparking spirited conversation in an intimate, artful setting.
The next stop is a brief, inviting walk over to Potts Point, transitioning to a food-centric wine bar known for its warm hospitality.
A beloved Potts Point hotspot where approachable sophistication reigns, featuring thoughtfully selected wines and refined share plates that fuel the crawl’s social and flavorful momentum.
The next stop is just around the corner, keeping the energy flowing as you step into a cozy, retro-inspired venue celebrating cured meats and Italian influences.
This snug Potts Point diner offers an engaging blend of cured meats, fresh seafood, and pasta in a retro setting, encouraging lively chats and shared plates that enhance the crawl’s communal spirit.
The next stop is a short, charming walk through Potts Point’s leafy streets, leading to a Victorian house turned Italian wine and food retreat.
Wrap up your journey in this inviting Victorian house where gourmet sourdough pizzas and fresh seafood meet an impressive Italian wine list, delivering a final flourish of authentic flavors and warm ambiance.
The next stop is the end of the crawl, leaving you perfectly poised for lingering conversations and plans for the next adventure.
This 7-stop Woolloomooloo wine bar crawl is a curated odyssey through Sydney’s most captivating wine destinations, each offering a unique flavor and vibe that keeps energy high and palates delighted. From harbourfront glamour to intimate laneway hideaways and charming Victorian retreats, this journey celebrates the art of wine and the joy of connection. Whether you’re reveling with friends or meeting new faces, every pour promises discovery and delight. So lace up your walking shoes, gather your crew, and let Woolloomooloo’s wine bars show you the spirited side of Sydney nightlife—one glass at a time.
Crawl Map