đź“… Open Today: Crawl likely open on Sundays
Embark on a delightful wine bar crawl in Sydney, visiting Macchiato Wood Fire Pizza and Coffee Roasters, Mille Vini Wine Bar & Restaurant, and The Winery. Indulge in rustic-chic decor, wood-fired pizza, and an array of fine wines. Whether you're a wine enthusiast or just looking for a fun night out, this crawl promises a memorable experience filled with good drinks and great company.
Last updated: May 2025
Shop 2/338 Pitt Street, Sydney
~1149m walk to next stop
Dive headfirst into Sydney’s dynamic wine scene with this carefully curated three-stop crawl that ignites the night with energy and flavor. Begin your journey at Macchiato Wood Fire Pizza and Coffee Roasters, where rustic Italian warmth meets lively group energy amid the glow of wood-fired ovens. Next, elevate the tempo with Mille Vini Wine Bar & Restaurant’s sophisticated European tasting plates and smooth live jazz, crafting an intimate yet spirited atmosphere perfect for deepening connections. Finally, lose yourself in the chic bohemian vibe of The Winery, where lush outdoor seating and an impressive wine-by-the-glass list offer a stylish crescendo to your adventure. This crawl perfectly balances bold tastes and vibrant social scenes, creating an irresistible Sydney night out that pulses with excitement from start to finish.
Kick off the crawl at Macchiato, where lively energy and rustic wood-fired flavors set an inviting, upbeat tone. This spot’s casual Italian vibe and buzzing atmosphere fuel the social sparks and prepare you for the journey ahead with hearty dishes and vibrant buzz.
The next stop is a lively 15-minute stroll south to Surry Hills, giving you a chance to soak in Sydney’s urban buzz and build anticipation for a shift to elevated European sophistication.
Mille Vini raises the bar with rustic European elegance and an intimate, jazz-accented ambiance. It’s the perfect mid-crawl destination to deepen your tasting experience with refined wines and artisanal plates, while the lively but intimate vibe keeps the energy flowing.
The next stop is a quick 5-minute walk down Crown Street, where the scene shifts again to a bohemian-chic laneway sanctuary buzzing with stylish nightlife energy.
End your adventure at The Winery, a stylish Surry Hills gem that combines modern Australian flavors with a vibrant, upscale atmosphere. Its lush outdoor spaces and extensive curated wine list create a celebratory finale where the night’s energy peaks in style.
The next stop is the perfect final destination—no more walking needed, just settle in and savor the moment.
This Sydney wine bar crawl is your ticket to an unforgettable night of social adventure, bold flavors, and ever-evolving vibes. Whether you’re celebrating with friends or igniting new connections, each stop offers a fresh burst of energy and taste to carry you through the evening. So gather your crew, map your route, and prepare to sip, savor, and socialize your way across Sydney’s most dynamic wine bars. The city’s vibrant nightlife awaits—let the adventure begin!
Crawl Map