đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s best cocktail bars on this fun-filled crawl! Visit five unique venues, from snug ship-themed spots with plush couches to lively tiki mug lounges filled with creative drinks. Whether you’re into rum, cocktails, or just soaking up the quirky neighbourhood vibe, this crawl has it all. Perfect for a relaxed night out with friends, enjoying DJ parties, cozy booths, and a lively atmosphere. Cheers to a memorable Windsor night!
Last updated: July 2025
Get ready to ignite your night on Windsor’s iconic Chapel Street, where every stop on this cocktail bar crawl promises a fresh burst of energy and flavor. Starting with the quirky charm of a neighborhood favorite, you’ll journey through playful lounges, nostalgic game havens, and cozy ship-themed escapes before ending in a lush tropical oasis. Each venue brings a distinct personality—whether it's infectious beats, inventive cocktails, or welcoming crowds—ensuring your night builds from lively beginnings to a spirited crescendo. This crawl isn’t just about drinks; it’s a social adventure packed with laughter, discovery, and unforgettable moments.
Kick off your night at Three Monkeys, where quirky character meets pulsating weekend DJ energy. This intimate space sets an upbeat tone with expertly mixed cocktails and a vibrant buzz that invites connection and celebration.
The next stop is a short, lively stroll down Chapel Street, keeping the momentum alive as you move towards a spot that mixes nostalgia and playful fun.
At Better Days, dive into a playground of board games, nostalgic video entertainment, and inventive cocktails. This stop amps up the social vibe, perfect for sparking laughter and friendly competition.
The next stop is just a quick, buzzing walk along Chapel Street, where the energy shifts toward sophisticated sips and elegant gatherings.
Blackwoods elevates the crawl with a polished yet approachable ambiance, offering refined cocktails and a curated wine list. It’s the perfect bridge from playful to poised, welcoming both intimate conversations and lively group cheers.
The next stop is a brisk, inviting walk that leads you into a themed setting bursting with character and cozy sophistication.
Step aboard Holy Grail’s ship-inspired lounge, where plush seating and expertly crafted rums create a warm yet spirited atmosphere. This stop anchors the night with a blend of comfort and excitement, perfect for savoring cocktails alongside tasty bites.
The next stop is a short, energetic walk that transports you from nautical charm to a vibrant tropical escape.
Finish strong at Jungle Boy, a lively tropical lounge bursting with lush plants and exotic cocktails served in iconic tiki mugs. This spirited finale invites you to immerse yourself in bold flavors and vibrant surroundings, rounding out the crawl with unforgettable flair.
The crawl concludes here, leaving you perfectly poised to continue the night or savor the lasting buzz of a truly adventurous escapade.
This Windsor cocktail bar crawl delivers an exhilarating journey through Chapel Street’s most dynamic venues. Whether you’re chasing inventive drinks, lively social scenes, or immersive atmospheres, each stop builds on the last to craft an unforgettable night out. Gather your crew, bring your sense of adventure, and toast to the vibrant spirit of Windsor’s cocktail culture. Ready to make memories? Let the crawl begin!
Crawl Map