đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s hidden gem cocktail bars on this lively crawl! From snug, ship-themed spots with plush couches to plant-filled lounges serving tiki mugs, you’ll explore five unique venues including Three Monkeys, Better Days, Blackwoods, Holy Grail, and Jungle Boy. Whether you're into rum, cocktails, or weekend DJ parties, this crawl offers a perfect mix of quirky atmospheres and great drinks in a friendly, neighbourhood setting. Grab your friends and get ready for a memorable night out!
Last updated: July 2025
Get ready to ignite your night with the Windsor Cocktail Bar Crawl, a carefully crafted journey through Chapel Street’s most energetic and spirited cocktail destinations. This crawl pulses with lively energy, starting in intimate and quirky settings before ramping up the fun with playful games and inventive concoctions. As the night unfolds, sophisticated sippers will appreciate expert craftsmanship and curated wine selections, before sinking into the plush, ship-themed ambiance of Holy Grail. The adventure culminates at Jungle Boy, where tropical greenery and daring tiki cocktails spark a vibrant, unforgettable finale. Whether you’re rallying friends or making new ones, this crawl promises an exhilarating social adventure packed with bold flavors and dynamic atmospheres.
Kick off the crawl at Three Monkeys, where quirky charm meets vibrant energy. This snug spot sets the tone with expertly crafted cocktails and weekend DJ sessions that spark immediate excitement and social buzz.
The next stop is a short, lively stroll down Chapel Street, keeping the buzz flowing as you head to Better Days Cocktail Bar.
Dive into a playful atmosphere at Better Days, where inventive cocktails meet fun board and video games. This stop injects a burst of interactive energy, perfect for sparking laughter and friendly competition.
The next stop is a brief walk along Chapel Street, letting the night’s energy build as you approach Blackwoods Wine & Cocktail Bar.
Elevate the evening at Blackwoods, where sophisticated cocktails and a curated wine list create a polished yet unpretentious vibe—ideal for gathering your group and savoring expertly crafted drinks.
The next stop is a lively stroll down Chapel Street, transitioning from refined sips to the cozy, ship-themed ambiance of Holy Grail.
Step into Holy Grail’s ship-inspired sanctuary, where plush seating and a fine rum selection invite effortless conversations and a comforting, yet spirited atmosphere—perfect for both intimate moments and group celebrations.
The next stop is a quick walk along Chapel Street, setting the stage for a tropical finale at Jungle Boy.
Cap off the crawl in style at Jungle Boy, where lush greenery and exotic tiki cocktails create a vibrant, adventurous vibe. This energetic finale wraps the night with bold flavors and a spirited social scene.
This final stop ends the crawl right in the heart of Windsor’s nightlife scene.
As the night winds down, reflect on the adventure through Windsor’s cocktail hotspots that perfectly blend creativity, energy, and sociability. Whether you’re a cocktail connoisseur or simply chasing great vibes, this crawl offers an exhilarating journey that transforms Chapel Street into your personal playground. Ready to raise a glass and make unforgettable memories? Grab your crew and dive into Windsor’s ultimate cocktail escapade tonight!
Crawl Map