đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant nightlife with our cocktail bar crawl! Visit five unique venues, from ship-themed cozy spots like Three Monkeys to lush, plant-filled lounges like Jungle Boy. Discover quirky neighbourhood hangouts with plush couches, antique chairs, and lively DJ parties on weekends. Perfect for cocktail lovers and fun-seekers alike, this crawl offers a mix of rum, tiki mugs, and creative drinks in welcoming, stylish settings. Cheers to an unforgettable night out!
Last updated: July 2025
Windsor’s Chapel Street bursts to life after dark, and this cocktail bar crawl captures its pulse perfectly. Kicking off with Three Monkeys’ lively, quirky atmosphere and weekend DJ grooves, the night sets an upbeat tone. Next, dive into the infectious energy of Better Days, where board games and nostalgia fuel laughter and connection. As the crawl unfolds, Blackwoods Wine & Cocktail Bar invites a touch of elegant vibrancy, balancing the night with refined cocktails and convivial chatter. Then, step aboard Holy Grail’s ship-inspired sanctuary, where plush seating and rich rum selections create a unique, immersive vibe. Finally, Jungle Boy wraps the night in lush tropical warmth, serving up daring tiki cocktails in a plant-filled lounge that’s equal parts stylish and inviting. This crawl offers a dynamic journey through flavor, atmosphere, and fun—perfect for those ready to explore Windsor’s spirited nightlife scene.
Launch your night with Three Monkeys’ vibrant blend of quirky charm and pulsing DJ weekends—setting an energetic, engaging tone that sparks conversation and celebration.
The next stop is a short, lively stroll down Chapel Street, keeping the energy flowing as you head to Better Days Cocktail Bar.
Better Days shifts the vibe to playful and sociable, where inventive cocktails meet nostalgic board games and video classics, perfect for connecting and sharing laughs.
The next stop is a brief walk along Chapel Street, maintaining the upbeat momentum toward the refined atmosphere of Blackwoods Wine & Cocktail Bar.
Blackwoods elevates the crawl with a sophisticated yet lively setting, offering expertly crafted cocktails and a warm ambiance that invites both intimate chats and group celebrations.
The next stop is a quick and enjoyable walk down Chapel Street, leading you to the distinct, immersive world of Holy Grail.
Step into Holy Grail’s ship-themed refuge, where plush seating and a rich rum collection create a cozy yet spirited environment—perfect for savoring cocktails in style and comfort.
The next stop is just minutes away on Chapel Street, guiding you toward the tropical oasis of Jungle Boy to close out the night.
Jungle Boy caps off the crawl with lush greenery, vibrant tiki cocktails, and a welcoming vibe that turns every sip into an adventurous celebration of flavor and fun.
This is the final stop, perfectly situated to unwind or keep the night rolling in Windsor’s lively nightlife scene.
Ready to dive into Windsor's spirited cocktail culture? This crawl delivers a curated blend of energy, creativity, and social connection across Chapel Street’s standout bars. Whether you’re hunting for expertly crafted drinks, nostalgic fun, or tropical escapes, each stop adds its own spark to an unforgettable night out. Gather your crew, pace yourself, and let Windsor’s cocktail scene surprise and delight at every turn. Cheers to a night of discovery and dynamic fun!
Crawl Map