đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s coolest cocktail bars on this lively crawl! From snug, ship-themed hideaways serving rum and cocktails to plant-filled lounge spots with tiki mugs, you'll explore 5 unique venues including Three Monkeys, Better Days, Blackwoods, Holy Grail, and Jungle Boy. Whether you're into cozy booths, DJ parties, or quirky neighbourhood hangouts, this crawl offers a memorable night out filled with great drinks, fun vibes, and plenty of surprises. Perfect for anyone wanting to sip, socialize, and soak up Windsor’s vibrant bar scene!
Last updated: July 2025
Embark on a spirited journey through Windsor’s lively Chapel Street, where every stop delivers a fresh twist on cocktail culture. This crawl kicks off with the infectious energy of Three Monkeys, a quirky hotspot where expertly mixed drinks meet weekend DJ rhythms, setting the tone for a night full of social sparks. Next, dive into a playful atmosphere at Better Days Cocktail Bar, where board games and nostalgia mix seamlessly with inventive cocktails. The momentum builds as you arrive at Blackwoods Wine & Cocktail Bar, a refined yet approachable venue perfect for savoring sophisticated drinks with friends. Then, step aboard the ship-inspired Holy Grail, where plush seating and a standout rum selection invite you to unwind while staying engaged. Finally, cap off the evening at Jungle Boy, a tropical oasis alive with lush greenery and daring tiki-style creations that keep the excitement flowing until last call. This crawl delivers a dynamic blend of energy, creativity, and camaraderie, promising an unforgettable night out in Windsor.
Kick-start the crawl at Three Monkeys, where lively weekend DJ sessions and expertly crafted cocktails create an electric atmosphere that instantly energizes the night.
The next stop is a short, engaging stroll down Chapel Street, keeping the vibrant buzz alive as you head to a playful cocktail haven.
Better Days blends nostalgia and inventive drinks, offering a spirited setting filled with board games and friendly competition that elevates the social vibe.
The next stop is a quick walk along Chapel Street, maintaining a steady rhythm as you approach a sophisticated yet welcoming cocktail spot.
Blackwoods brings a polished yet approachable energy, perfect for savoring refined cocktails while deepening connections in an elegant atmosphere.
The next stop is a lively walk just a few minutes away, shifting the mood toward a uniquely themed space that invites intimate conversations and group fun.
Holy Grail’s ship-themed interior and curated rum collection offer a cozy yet spirited pause, balancing plush comfort with dynamic flavors that keep the night rolling.
The next stop is a brief, refreshing walk nearby, leading to a vibrant tropical lounge that amps up the adventure for the final round.
Jungle Boy caps the crawl with a burst of tropical energy, where lush greenery and exotic tiki cocktails craft an unforgettable finale full of flair and fun.
The crawl ends here, in this lush oasis, leaving you perfectly poised to celebrate the night’s adventures or plan your next journey.
This Windsor cocktail bar crawl invites you to dive deep into the city’s dynamic scene, blending inventive concoctions with vibrant atmospheres and social thrills. Whether you're a cocktail connoisseur or simply craving an adventurous night out, these five stops deliver unforgettable moments and fresh flavors. Gather your crew, bring your curiosity, and let Chapel Street’s best bars light up your evening with energy and excitement. Ready to raise your glass and make memories? Start planning your Windsor cocktail adventure today!
Crawl Map