đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant nightlife on our cocktail bar crawl! Visit four unique venues including Three Monkeys, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, and Holy Grail. From cosy ship-themed bars with plush couches and antique chairs to lively DJ nights on weekends, this crawl is perfect for rum lovers and cocktail enthusiasts alike. Discover hidden gems, enjoy quirky neighbourhood hangouts, and sip your way through Windsor’s best bars—all in one unforgettable night out!
Last updated: July 2025
Windsor’s Chapel Street pulses with personality, and this cocktail crawl captures every thrilling beat. Start your evening at Three Monkeys, where infectious energy and expertly mixed drinks set a lively tone. Then, shift gears at Better Days Cocktail Bar—where nostalgia meets inventive cocktails amid board games and retro video vibes, sparking playful social moments. Next, elevate your night with the elegant yet approachable ambiance of Blackwoods Wine & Cocktail Bar, a perfect spot to mingle over refined drinks and curated wines. Finally, step aboard the ship-inspired Holy Grail, where plush seating and a stellar rum selection invite relaxed conversations and unforgettable group celebrations. This crawl builds an exciting flow from energetic starts to a captivating finish, ensuring every moment is a discovery in Windsor’s spirited cocktail culture.
Launch the night with Three Monkeys’ infectious energy, where quirky charm meets lively DJ sets and crafted cocktails that ignite the social spark.
The next stop is a quick stroll along Chapel Street to Better Days Cocktail Bar, keeping the momentum lively and inviting you into a playful atmosphere.
Dive into a spirited mix of nostalgia and creativity at Better Days, where board games and inventive cocktails fuel animated conversations and shared laughter.
The next stop is a short walk down Chapel Street to Blackwoods Wine & Cocktail Bar, transitioning the vibe toward sophisticated yet welcoming sips.
Elevate your crawl with Blackwoods’ refined cocktail craftsmanship and curated wines, offering a stylish yet approachable spot for connecting and savoring every sip.
The next stop is a brief walk to the ship-themed Holy Grail, where the evening’s energy finds a warm and inviting harbor.
Anchor your night at Holy Grail’s plush, ship-inspired space, where handcrafted rum cocktails and cozy booths create the perfect setting for memorable late-night conversations and celebrations.
The next stop concludes the crawl here, wrapping up with a richly satisfying finale in Windsor’s cocktail scene.
This Windsor cocktail crawl takes you on a vibrant journey through Chapel Street’s best spots, blending eclectic vibes with crafted drinks and social thrills. Whether you’re rallying friends or making new ones, each bar offers a unique chapter in an unforgettable night of spirited adventure. Ready to sip, play, and explore? Lace up your walking shoes and let Windsor’s cocktail pulse guide your evening.
Crawl Map