đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant nightlife with our cocktail bar crawl! Discover five fantastic venues, from the ship-themed Three Monkeys to the lush, plant-filled Jungle Boy, each offering unique vibes and amazing drinks. Whether you’re into rum and cocktails in a cosy setting or dancing at DJ parties on weekends, this crawl has something for everyone. Perfect for a fun, laid-back night out with friends in Windsor’s coolest neighbourhood hangouts.
Last updated: July 2025
Kick off your night in Windsor with an exhilarating cocktail bar crawl that pulses with energy and crafted creativity. From the moment you step into Three Monkeys, the scene is set with infectious beats and expertly shaken drinks, perfect for sparking conversation and igniting the evening’s spirit. As you weave through Chapel Street, each stop offers a fresh twist — playful nostalgia meets inventive mixology at Better Days, while Blackwoods invites you to indulge in a refined yet approachable atmosphere that effortlessly balances sophistication with spirited fun. The journey continues with the ship-themed charm and rich rums of Holy Grail, where plush seating encourages lingering and laughter. Finally, Jungle Boy caps the crawl with a lush, tropical ambiance and daring tiki cocktails that awaken the senses. This carefully curated lineup ensures your night unfolds with escalating excitement, blending social adventure with memorable flavors and atmospheres.
Set the night ablaze at Three Monkeys, where a quirky, vibrant atmosphere and weekend DJ sessions fuel energetic introductions and conversation-stirring cocktails.
The next stop is a brief, lively stroll along Chapel Street to Better Days, keeping the momentum flowing with street-side buzz and anticipation.
Better Days amps up the fun factor with its playful board games and nostalgic video projections, making it the perfect spot to mix inventive cocktails with friendly competition.
The next stop is a quick, spirited walk down Chapel Street to Blackwoods, offering time to savor the vibrant urban energy surrounding you.
Blackwoods introduces an elegant yet inviting vibe, where meticulous cocktails and a curated wine list create a refined pause before the adventure continues.
The next stop is a comfortable walk further along Chapel Street to Holy Grail, letting the night’s energy shift toward cozy indulgence.
At Holy Grail, the nautical-themed setting and rich rum selections create a plush, immersive environment ideal for deepening connections and savoring crafted cocktails.
The next stop is a short, invigorating walk to Jungle Boy, where the atmosphere turns tropical and playful for an unforgettable finale.
Jungle Boy closes the crawl with a burst of tropical flair, blending lush greenery, exotic tiki mugs, and bold cocktails that leave a lasting impression.
The crawl concludes here, inviting you to linger or explore Windsor’s nightlife further on your own adventurous terms.
This Windsor cocktail bar crawl is your ticket to an electrifying night packed with dynamic settings and masterful mixology. Each venue brings its own flavor and character, ensuring every sip and step offers fresh excitement and connection. So gather your crew, bring your curiosity, and dive headfirst into Chapel Street’s spirited cocktail scene—your next memorable night out starts here.
Crawl Map