đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our exciting bar crawl featuring 5 fantastic venues! From cosy, ship-themed rum & cocktail bars with plush couches to trendy plant-filled lounges serving tiki mugs, this crawl offers a diverse mix of food-centric pubs, stylish bars, and lively nightspots. Perfect for a night out with friends, enjoy signature drinks, unique atmospheres, and unforgettable memories across venues like Naughty Nancy's, Better Days, Blackwoods, Holy Grail, and Jungle Boy. Cheers to good times!
Last updated: July 2025
Kick off your night on Windsor’s vibrant Chapel Street with a cocktail bar crawl designed to energize your senses and fuel your social spirit. This journey unfolds with Naughty Nancy’s infectious buzz of live music and hearty bites, setting the tone for an evening of spirited fun. As you wander, Better Days Cocktail Bar invites you into a playground of board games and nostalgic vibes, where craft cocktails spark laughter and connection. The crawl then flows into the refined yet lively atmosphere of Blackwoods Wine & Cocktail Bar, where expertly crafted drinks match the lively chatter. Next, Holy Grail welcomes you aboard its ship-themed refuge, serving up rum-forward cocktails in a cozy, inviting setting that blends intimacy with buzz. Finally, Jungle Boy caps the night with its lush tropical oasis, delivering exotic tiki cocktails that spark adventure and celebration. Each stop shifts the energy just right, creating a dynamic night that balances playful exploration with bold flavors and unforgettable moments.
Launch your night at Naughty Nancy’s where live music and craft cocktails collide with a food-centric atmosphere, igniting an electric energy that gets the social pulse racing.
The next stop is a short, lively stroll further down Chapel Street, maintaining the night’s vibrant momentum.
Shift into a playful groove at Better Days, where inventive cocktails meet board games and nostalgic video classics, creating an upbeat and interactive vibe perfect for sparking new connections.
The next stop is a brief, engaging walk along Chapel Street, keeping the energy flowing seamlessly.
Elevate the evening at Blackwoods with expertly crafted cocktails and a curated wine list, offering a lively yet refined setting that invites animated conversations and celebration.
The next stop is a quick and easy stroll that naturally transitions the vibe toward a cozy, themed experience.
Step into Holy Grail’s ship-inspired ambiance where plush seating and a stellar rum selection create an inviting yet energized space for deep chats or spirited group toasts.
The next stop is a short, refreshing walk that shifts the atmosphere toward a vibrant tropical finale.
Cap off your night at Jungle Boy’s lush, plant-filled lounge, where exotic tiki cocktails and a lively tropical vibe turn the final moments into an adventurous celebration.
The crawl concludes here, leaving you perfectly poised to continue your night or savor the afterglow.
From the first sip to the last clink of a tiki mug, this Windsor cocktail bar crawl invites you to experience Chapel Street’s dynamic pulse with every step. Whether you’re chasing live music, playful games, refined drinks, or tropical escapes, this journey threads together vibrant scenes and bold flavors into one unforgettable night. Gather your crew, bring your adventurous spirit, and dive deep into Windsor’s spirited cocktail culture — the night awaits, and every bar is a new story waiting to be told.
Crawl Map