đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our exclusive bar crawl! Visit five unique venues including the snug Three Monkeys, the ship-themed Blackwoods, the plant-filled Jungle Boy, the cozy Holy Grail, and the lively Better Days. Whether you're into rum, tiki mugs, or DJ parties on weekends, this crawl offers a mix of quirky neighbourhood hangouts, plush couches, antique chairs, and lively vibes. Perfect for a fun, relaxed night out with friends—cheers!
Last updated: July 2025
Dive headfirst into Windsor’s buzzing Chapel Street with a cocktail bar crawl designed to ignite your night with energy, creativity, and unforgettable social moments. Begin at Three Monkeys, where quirky charm meets DJ-driven weekends, setting a dynamic tone. Then, shift gears to Better Days Cocktail Bar’s playful ambiance, blending nostalgia and craft cocktails with lively games. Next, indulge in refined flavors at Blackwoods Wine & Cocktail Bar, a seamless bridge between casual and classy. Ready for a theme twist? Holy Grail’s ship-inspired setting invites you to unwind with rich rums and sharing plates. Finally, cap off your adventure at Jungle Boy, a tropical oasis where exotic cocktails in tiki mugs elevate the excitement. Each stop offers a fresh vibe and a new way to connect, making this crawl an electrifying journey through Windsor’s cocktail scene.
Kick off your crawl at Three Monkeys, where energetic beats and quirky charm blend into an inviting hub for expertly crafted cocktails and vibrant socializing that sets the night’s lively pace.
The next stop is a brief, easy stroll along Chapel Street, keeping the momentum alive with sights of Windsor's bustling nightlife.
Shift into playful mode at Better Days, where inventive cocktails meet retro games and cozy corners—perfect for sparking laughter and friendly competition as the energy builds.
The next stop is just a short walk down the street, inviting you to soak in more of Chapel Street’s vibrant evening buzz.
Elevate the vibe with Blackwoods’ sophisticated yet approachable atmosphere, offering polished cocktails and curated wines that provide a seamless transition from playful fun to refined indulgence.
The next stop is a quick stroll that brings you deeper into Windsor’s dynamic bar scene, maintaining the night’s spirited flow.
Step aboard Holy Grail’s ship-themed sanctuary to enjoy rich rums, handcrafted cocktails, and a spacious setting that balances lively group energy with intimate conversation spots.
The next stop is a lively walk along Chapel Street, keeping energy levels high with Windsor’s neon-lit evening vibe.
Conclude your crawl in Jungle Boy’s tropical lounge, where lush greenery, daring tiki cocktails, and a spirited atmosphere deliver a memorable finale bursting with exotic flavors and friendly buzz.
The crawl ends here, right in the heart of Windsor’s nightlife, perfect for lingering or continuing your night’s adventures.
From upbeat beats to tropical escapes, this Windsor cocktail bar crawl promises a night packed with flavor, fun, and friendship. Whether you’re a cocktail connoisseur or just chasing good times, these five stops along Chapel Street offer the perfect blend of energy and adventure. Ready to raise your glass and explore Windsor’s spirited side? Gather your crew, bring your appetite for excitement, and dive into an unforgettable night out.
Crawl Map