đź“… Open Today: Crawl likely not fully open on Sundays
Embark on a wine bar crawl in Sydney, featuring Hotel Downing, Mille Vini Wine Bar & Restaurant, and The Winery. Indulge in Rustic European tasting plates and pasta dishes, sip on cocktails, and enjoy the classy ambiance. Perfect for a fun night out with friends!
Last updated: May 2025
Get ready to unleash your adventurous spirit with Sydney’s ultimate 3-stop wine bar crawl. Starting in the city’s heart, this journey kicks off with the warm, unpretentious buzz of Hotel Downing, where bold pub flavors and inviting house wines set the tone for a night packed with lively conversation and good cheer. Next, venture into the soulful streets of Surry Hills to Mille Vini, a rustic European gem that turns wine tasting into an experience wrapped in live jazz and handcrafted plates. Finally, step into the chic, bohemian atmosphere of The Winery, where lush garden vibes and an impressive wine list elevate your evening into a stylish celebration of Modern Australian cuisine. This crawl isn’t just about sipping wine — it’s a social adventure that builds momentum, weaving energy, elegance, and epicurean delights into one unforgettable night.
Launch your crawl with Hotel Downing’s vibrant pub atmosphere, where hearty dishes and approachable house wines fuel the night’s energy while sparking lively connections.
The next stop is a refreshing stroll to Surry Hills, shifting the vibe from city buzz to a charming neighborhood feel.
Mille Vini elevates the evening with rustic European wines and plates, accompanied by live jazz that adds a rhythmic pulse, infusing the crawl with warmth and spirited elegance.
The next stop is a short, inviting walk deeper into Surry Hills’ laneways, where style and sophistication await.
Cap off your night at The Winery, where a bohemian-chic setting and an extensive wine-by-the-glass selection provide the perfect backdrop for a lively finale filled with fresh flavors and garden-side vibes.
The crawl concludes here, leaving you immersed in Surry Hills’ vibrant wine culture.
This Sydney wine bar crawl wraps up your night on a high note, blending bold flavors, dynamic atmospheres, and social buzz into one seamless experience. Whether you're a wine aficionado or simply chasing memorable nights, this itinerary promises excitement at every turn. Ready to embark? Grab your friends, pace your palate, and let Sydney’s spirited wine scene guide your next adventure.
Crawl Map