đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant cocktail scene with our curated pub crawl featuring 5 awesome venues. Sip rum and creative cocktails in a ship-themed bar at Three Monkeys, dance to DJ beats at Holy Grail, or relax in a lush, plant-filled lounge at Jungle Boy. Whether you’re into cozy snug spots or lively weekend parties, this crawl offers a quirky mix of neighbourhood hangouts and stylish bars, perfect for a fun night out with friends. Cheers to great drinks and even better company!
Last updated: July 2025
Windsor’s Chapel Street pulses with energy and creativity, and this cocktail bar crawl is your ticket to experiencing its dynamic spirit. Begin your evening at Three Monkeys, where quirky charm and weekend DJ beats set a vibrant social tone. As you move along, Better Days Cocktail Bar invites you to unleash your playful side with board games and inventive concoctions that spark laughter and connection. Next, Blackwoods Wine & Cocktail Bar offers an elegant yet lively atmosphere, perfect for raising a glass with friends or new acquaintances. The journey continues to Holy Grail’s ship-inspired warmth, blending plush comfort with expertly mixed rum cocktails that invite easy conversation and memorable moments. Finally, Jungle Boy transports you to a tropical hideaway where lush greenery and exotic tiki mugs elevate your night to a spirited crescendo. Each stop builds on the last, crafting an unforgettable night of crafted cocktails, lively vibes, and social adventure.
Kick off the crawl in a quirky, intimate setting alive with infectious energy and weekend DJ rhythms, where expertly crafted cocktails spark the night’s excitement.
The next stop is a short stroll down Chapel Street, keeping the lively energy flowing as you head to a spot where playfulness meets cocktail creativity.
Turn up the fun with a vibrant hangout featuring cozy couches, board games, and inventive cocktails that fuel laughter and social connection.
The next stop is just a few minutes on foot, allowing you to savor the buzz of Chapel Street as you transition to a more elegant yet lively setting.
Elevate the night at a stylish yet unpretentious bar where refined cocktails and a curated wine list keep the momentum vibrant and the atmosphere inviting.
The next stop is a brief walk, shifting the vibe toward a cozy, themed venue perfect for intimate chats and expertly crafted drinks.
Immerse yourself in a ship-inspired setting with plush seating and a stellar rum selection, offering a warm yet spirited atmosphere to deepen connections.
The next stop is a quick walk along Chapel Street, preparing you for a lively tropical finale amid lush greenery and exotic cocktails.
Cap off the crawl in a vibrant, plant-filled lounge where tiki mugs and bold cocktails create a festive tropical escape and unforgettable nightcap.
The crawl ends here, nestled on Chapel Street—perfect for lingering over one last adventurous cocktail or planning your next night out.
This Windsor cocktail bar crawl delivers a perfectly paced night of contrasts and continuity—from quirky beginnings to tropical finales. Each venue brings its own unique spark, ensuring your evening is packed with creative cocktails, buzzing social scenes, and memorable moments. So gather your crew, step into Chapel Street’s hottest bars, and toast to a night of pure adventure and spirited fun. Ready to dive in? The bars are waiting.
Crawl Map