đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant nightlife with our exciting cocktail bar crawl! Visit five fantastic spots including Naughty Nancy's, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, Holy Grail, and Jungle Boy. From cosy ship-themed rum & cocktail bars with plush couches to trendy plant-filled lounges serving tiki mugs, there's something for everyone. Perfect for foodies, social butterflies, and cocktail lovers looking for a memorable night out in Windsor!
Last updated: July 2025
Embark on a whirlwind cocktail adventure through Windsor’s buzzing Chapel Street, where each stop unfolds a fresh scene packed with creative concoctions and contagious energy. Begin your night at Naughty Nancy’s, a hotspot pulsating with live music and robust flavors that set the tone for an unforgettable evening. Glide into the nostalgic charm of Better Days, where board games and playful vibes spark laughter and camaraderie. Shift gears at Blackwoods, where sophistication meets warmth with polished cocktails and a curated wine list. Then, dive into the ship-inspired sanctuary of Holy Grail, where rum takes center stage amid plush seating and inviting conversations. Finally, cap off your crawl at Jungle Boy, a vibrant tropical oasis serving up bold tiki cocktails in an intimate, plant-filled atmosphere. This crawl is a dynamic journey through Windsor’s cocktail creativity, designed to ignite your spirit and connect you with the city’s lively social pulse.
Kick off your crawl at Naughty Nancy’s, where live music and a vibrant crowd fuel an electrifying atmosphere. This food-centric pub offers more than cocktails—think hearty bites and craft drinks that energize your night from the first sip.
The next stop is just a short, lively stroll along Chapel Street, keeping the buzz alive as you head to Better Days Cocktail Bar.
At Better Days, playful nostalgia takes center stage with board games and video classics paired with inventive cocktails. This spot invites you to unwind while keeping the energy upbeat and social, perfect for sparking new connections or friendly competition.
The next stop is a brief walk down Chapel Street, transitioning seamlessly to the refined yet welcoming vibe of Blackwoods Wine & Cocktail Bar.
Blackwoods elevates the crawl with its polished cocktail craftsmanship and curated wine selection. This elegant yet approachable venue offers a sophisticated backdrop to deepen conversations and toast the night with style.
The next stop is a quick, inviting stroll to Holy Grail, where a ship-themed setting awaits to elevate the rum and cocktail experience.
Step aboard Holy Grail’s ship-inspired bar to soak in cozy, plush surroundings while savoring expertly crafted rum cocktails and tasty finger foods. This stop blends comfort and character, perfect for lively group moments or intimate chats with a spirited edge.
The next stop is a short walk further along Chapel Street, shifting the vibe toward a tropical cocktail escape at Jungle Boy.
Conclude your crawl at Jungle Boy, a lush, plant-filled lounge where daring tiki drinks and exotic flavors ignite the night. This vibrant finale invites you to raise your glass surrounded by tropical vibes and convivial energy.
The crawl ends here, leaving you energized and inspired by Windsor’s cocktail creativity.
Ready to dive into Windsor’s bold cocktail scene? This crawl offers an exhilarating mix of flavors, atmospheres, and social moments — from live music and nostalgic games to elegant sips and tropical escapes. Grab your crew or fly solo and let the Chapel Street spirit lead your night. Remember to pace yourself, savor every cocktail, and soak in the electric energy that only Windsor can deliver. Your ultimate cocktail adventure starts now!
Crawl Map