đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s coolest cocktail bars on this lively crawl! From cozy, ship-themed spots with plush couches and antique chairs to plant-filled lounges serving tiki mugs, you’ll hit 5 unique venues like Three Monkeys, Better Days, Blackwoods, Holy Grail, and Jungle Boy. Whether you’re into rum, cocktails, or lively DJ nights, this crawl promises a fun-filled evening in Windsor’s quirky neighbourhood hangouts. Get ready for great drinks, good vibes, and unforgettable memories!
Last updated: July 2025
Get ready to ignite your night with Windsor’s most dynamic cocktail bar crawl, weaving through Chapel Street’s lively heart. This adventure is all about electric energy, where every stop elevates the vibe and every cocktail tells a story. Begin at Three Monkeys, where quirky charm meets infectious weekend DJ energy, setting a vibrant tone. Then shift gears to Better Days, a social playground packed with classic games and crafty concoctions that spark laughter and connection. The journey continues with Blackwoods, offering a polished yet approachable scene that balances sophistication with spirited gatherings. Holy Grail’s ship-inspired setting ushers in a cozy yet lively ambiance, perfect for deep conversations over expertly mixed rums and cocktails. Finally, cap off the night at Jungle Boy, where tropical greenery and daring tiki drinks transport you to a festive escape. This crawl isn’t just a night out—it’s a pulse-racing social adventure that captures Windsor’s cocktail culture in full swing.
Kick off the crawl at Three Monkeys, where quirky charm and a lively atmosphere fuse into an energetic launchpad. The weekend DJ vibes and masterful cocktails set a spirited tone that energizes the night ahead.
The next stop is a quick, vibrant stroll along Chapel Street, keeping the momentum alive with the buzz of Windsor nightlife.
Step into Better Days to amplify the fun with inventive cocktails paired with a lively mix of retro board and video games, turning socializing into an interactive delight.
The next stop is a brief, easy walk that keeps you immersed in the energetic pulse of Chapel Street’s bustling scene.
Blackwoods offers a refined yet vibrant shift, balancing expertly crafted drinks with an inviting ambiance that suits both intimate conversations and spirited group energy.
The next stop is a short walk down Chapel Street, maintaining the lively flow as you move into a space with cozy charm and big personality.
Holy Grail’s ship-inspired décor and plush seating create a captivating setting for savoring rum-forward cocktails while the atmosphere hums with warmth and spirited camaraderie.
The next stop is an engaging stroll that transitions you from classic charm to tropical vibrancy, keeping energy levels soaring.
Conclude the crawl at Jungle Boy, where lush greenery and exotic tiki mugs deliver an immersive tropical finale that bursts with bold flavors and a lively yet intimate social buzz.
The next stop is the end of the crawl, leaving you in the heart of Chapel Street to continue your night or reflect on an unforgettable cocktail journey.
This Windsor cocktail crawl is more than a night out—it’s a curated journey through Chapel Street’s most energetic, inventive, and convivial bars. Each stop offers a fresh twist on the art of cocktail craft and social connection, inviting you to sip boldly, mingle freely, and embrace the vibrant spirit of Windsor’s nightlife. Ready to write your own story of spirited adventures? Lace up your walking shoes, gather your crew, and let the Windsor Cocktail Bar Crawl transform your evening into an electrifying celebration of flavor and fun.
Crawl Map