đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our exclusive bar crawl! Visit 5 fantastic venues, including Naughty Nancy's, Better Days, Blackwoods, Holy Grail, and Jungle Boy. From cosy ship-themed bars with plush couches and antique charm to plant-filled lounges serving tiki mugs, there's a perfect spot for every cocktail enthusiast. Whether you're into rum, creative cocktails, or just looking for a fun night out, this crawl has it all — great drinks, lively atmosphere, and memorable vibes. Cheers to a night to remember!
Last updated: July 2025
Windsor’s Chapel Street is calling all cocktail adventurers to embark on a night packed with energy, flavor, and unforgettable social moments. This crawl kicks off with the buzzing atmosphere of Naughty Nancy’s, where live music and hearty bites set the tone for a night of excitement. Next, slide into the playful realm of Better Days Cocktail Bar, where board games and nostalgic vibes fuel laughter and connection. As the night deepens, Blackwoods Wine & Cocktail Bar offers a sophisticated yet vibrant setting to savor expertly crafted drinks. The journey then sails into the cozy, ship-themed charm of Holy Grail, where rum and cocktails flow amid plush seating and intimate conversations. Finally, cap off the evening at Jungle Boy, a tropical oasis alive with lush greenery and daring tiki cocktails that promise a spirited finale. This crawl flows seamlessly from fresh energy to intoxicating adventures, promising a night that’s as dynamic as the city itself.
Kick off the crawl at Naughty Nancy’s, where an energetic pub vibe combined with live music and craft cocktails ignites the night with vibrant social energy and delicious food to fuel the fun.
The next stop is a short, animated stroll along Chapel Street that keeps the buzz alive, leading you to a bar where games and great drinks await.
Better Days amps up the playful side of the crawl with its cozy couches, board games, and inventive cocktails, offering a lively yet intimate space to spark new friendships and shared laughter.
The next stop is a quick, upbeat walk that lets the night’s momentum build as you approach a sophisticated spot for expertly crafted drinks.
Blackwoods introduces a refined yet lively atmosphere—perfect for savoring tailor-made cocktails and curated wines while engaging with attentive staff in a welcoming, elegant setting.
The next stop is an inviting stroll down Chapel Street that shifts the vibe toward a cozy, themed venue ready to serve up rum-filled delights.
Step into Holy Grail’s ship-inspired ambiance, where plush seating and carefully crafted cocktails create a comfortable yet spirited environment ideal for lively conversations and group toasts.
The next stop is a brief, lively walk that transitions the scene from classic charm to tropical adventure, setting the stage for a vibrant finale.
End the night at Jungle Boy, where lush greenery and exotic tiki cocktails deliver a burst of tropical energy, ensuring a memorable and exhilarating send-off to your Windsor cocktail adventure.
The crawl concludes here, leaving you perfectly positioned to celebrate late into the night or explore more of Chapel Street’s nightlife.
This Windsor cocktail bar crawl is your ticket to an unforgettable night fueled by bold flavors, engaging atmospheres, and vibrant social scenes. Whether you’re diving into live tunes, challenging friends to games, savoring sophisticated sips, or embracing tropical escapes, every stop is crafted to elevate your evening. Ready to ignite your night? Grab your crew, hit Chapel Street, and let the adventure unfold—cheers to lively nights and legendary stories in Windsor!
Crawl Map