đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our curated bar crawl! Visit five unique venues, including cozy, ship-themed bars like Holy Grail, lush jungle-inspired lounges like Jungle Boy, and stylish spots like Better Days. Whether you're into rum, tiki mugs, or lively DJ parties on weekends, this crawl offers a perfect mix of quirky, snug, and contemporary hangouts. Grab your friends and enjoy a memorable night exploring Windsor's coolest cocktail bars!
Last updated: July 2025
Embark on a spirited journey through Windsor’s vibrant Chapel Street, where each bar pulses with its own unique energy and cocktail mastery. This crawl kicks off with the infectious buzz of Three Monkeys, where DJ nights and expertly mixed drinks set the tone for an unforgettable evening. As you move on, soak up the playful charm of Better Days Cocktail Bar, where board games and vintage vibes spark laughter and connection. The crawl flows seamlessly into the welcoming elegance of Blackwoods Wine & Cocktail Bar, perfect for savoring refined cocktails with friends. Then, step aboard the ship-themed Holy Grail, where rum reigns supreme amidst plush seating and crafted bites. Finally, cap off your night at Jungle Boy, a lush tropical hideaway serving vibrant tiki cocktails that keep the energy alive. This crawl is a dynamic blend of lively atmospheres and adventurous flavors, designed to fuel your night with social thrills and unforgettable moments.
Kick off your night at Three Monkeys, where the upbeat vibe and weekend DJ sets create an electric atmosphere paired with sharp cocktails, igniting the social energy from the very first sip.
The next stop is a short, lively stroll along Chapel Street, keeping the vibrant energy flowing as you head to Better Days Cocktail Bar.
Better Days invites you to dive into an interactive scene with board games and nostalgic visuals that spark playful competition, perfectly complementing its inventive cocktails and upbeat vibe.
The next stop is just a quick walk further down Chapel Street, maintaining the crawl’s dynamic momentum as you approach Blackwoods Wine & Cocktail Bar.
Blackwoods brings a tasteful shift with its sophisticated yet approachable atmosphere, where expert cocktail craftsmanship meets a curated wine selection to elevate the night’s rhythm.
The next stop is a brief and engaging walk along Chapel Street, guiding you toward the distinct charm of Holy Grail.
Step into Holy Grail’s ship-inspired setting for a cozy yet lively experience, where rum-focused cocktails and inviting seating create a perfect blend of spirited fun and intimate conversation.
The next stop is a short walk, allowing the shift towards a tropical, vibrant finale at Jungle Boy.
Conclude your crawl in Jungle Boy’s lush, plant-filled lounge, where exotic tiki mugs and bold cocktails deliver a festive punch, keeping the night adventurous and the energy soaring until the last call.
The crawl ends here, in a vibrant oasis that leaves you buzzing with tropical vibes and cocktail creativity.
This Windsor cocktail bar crawl crafts an unforgettable night of discovery and delight, from energetic DJ beats to tropical tiki escapes. Perfect for cocktail enthusiasts and social adventurers alike, it invites you to explore Chapel Street’s best with friends by your side and a thirst for excitement. Ready to raise your glass and dive into Windsor’s spirited nightlife? Grab your crew, follow the trail, and let the cocktails—and good times—flow.
Crawl Map