đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant nightlife with our cocktail bar crawl, featuring five fantastic venues. From the ship-themed Three Monkeys with plush couches to the quirky Better Days Cocktail Bar and the tropical vibe of Jungle Boy, there's something for everyone. Enjoy rum & cocktails in cozy, funky spots with DJ parties on weekends. Perfect for a fun, relaxed night out with friends, exploring the best of Windsor’s quirky neighbourhood hangouts and lively atmosphere.
Last updated: July 2025
Dive headfirst into Windsor’s vibrant Chapel Street with a cocktail bar crawl designed for thrill-seekers and social adventurers alike. This journey kicks off in a quirky, upbeat setting where infectious energy sets the tone. Each bar brings its own distinct flavor — from playful gaming lounges and elegant wine-infused havens to nostalgic ship-themed retreats and lush tropical escapes. Along the way, expect inventive cocktails crafted with flair, atmospheres ripe for lively conversations, and seamless transitions that keep the momentum flowing. Whether you’re rallying friends or making new ones, this crawl promises a night rich in flavor, fun, and unforgettable moments.
Kick off your night at Three Monkeys, where a quirky interior and a lively weekend DJ vibe infuse the space with buzzing energy perfect for sparking connections over expertly crafted cocktails.
The next stop is just a quick, invigorating stroll down Chapel Street, keeping the pulse of the night alive as you advance.
Step into Better Days to amplify the fun with board games, nostalgic video game projections, and inventive cocktails that fuel friendly competition and laughter in an upbeat atmosphere.
The next stop is a short, energizing walk along Chapel Street, perfectly timed to build anticipation for the next highlight.
Elevate your experience at Blackwoods, where a curated wine list meets crafted cocktails in an elegant yet approachable setting, offering a sophisticated boost to the crawl’s vibrant momentum.
The next stop is a lively, inviting stroll further along Chapel Street, keeping the night’s rhythm seamless and exciting.
Unwind with a twist at Holy Grail’s ship-inspired retreat, where plush seating and a stellar rum selection set the stage for rich conversations and flavorful discoveries amid warm, vintage charm.
The next stop is an easy, anticipation-building walk along Chapel Street, guiding you into the crawl’s tropical finale.
Cap off the night at Jungle Boy, a plant-filled lounge serving exotic tiki-style cocktails in a lively, vibrant atmosphere that celebrates bold flavors and unforgettable social moments.
The next stop concludes the crawl here, letting you linger in this spirited oasis or continue your night in Windsor’s buzzing nightlife.
From the first cocktail to the last clink of a tiki mug, this Windsor crawl is a curated adventure through creativity, energy, and connection. Embrace the night’s dynamic flow, celebrate new friendships, and savor every unique sip along Chapel Street. Ready to raise your glass and dive into Windsor’s cocktail scene? Gather your crew, bring your sense of adventure, and let this crawl ignite your evening with unforgettable fun.
Crawl Map