đź“… Open Today: Crawl likely open on Fridays
Join us for an unforgettable Windsor cocktail bar crawl through five of the city’s coolest spots. Sip rum and craft cocktails in cozy, ship-themed locales like Three Monkeys and Blackwoods, enjoy vibrant DJ parties at Better Days, and unwind in jungle-inspired lounges like Jungle Boy. Perfect for a fun night out with friends, this crawl offers a mix of quirky neighbourhood hangouts and lively nightspots, all with great drinks and good vibes. Cheers to a night you’ll remember!
Last updated: July 2025
Embark on a spirited journey through Windsor’s Chapel Street, where each cocktail bar offers a fresh burst of energy and character. This crawl kicks off with the infectious buzz of Three Monkeys, a spot that fuses intimate charm with pulsating weekend DJ vibes. As you wander deeper, Better Days invites you to let loose with inventive cocktails paired with nostalgic games, sparking laughter and new connections. The momentum builds at Blackwoods, where expertly crafted drinks meet an inviting yet vibrant scene perfect for every kind of gathering. Then, lose yourself in the ship-inspired ambiance of Holy Grail, where plush seating and refined rums set the stage for lively conversations. Finally, cap off your night at Jungle Boy, an exotic oasis awash with tropical greenery and bold tiki cocktails, turning your Windsor night out into an unforgettable social adventure.
Kicking off the crawl with a contagious mix of cozy quirkiness and vibrant weekend beats, Three Monkeys sets an energetic tone that sparks instant social connection and cocktail excitement.
The next stop is a brief, lively stroll down Chapel Street that keeps the buzz alive as you head to Better Days Cocktail Bar.
Injecting playful energy with retro games, inventive drinks, and a welcoming vibe, Better Days offers a spirited contrast and a chance to mingle over shared laughter.
The next stop is just a short walk along Chapel Street, maintaining the crawl’s lively pace toward Blackwoods Wine & Cocktail Bar.
This bar elevates the night with elegant yet unpretentious cocktails and a vibrant atmosphere that suits both intimate chats and energetic group meetups.
The next stop is a quick, engaging stroll deeper into Chapel Street’s heart, leading to Holy Grail’s distinctive ship-themed setting.
Holy Grail’s unique nautical décor and rich rum offerings create a captivating mid-crawl vibe, blending cozy comfort with spirited conversation and crafted cocktails.
The next stop is a short walk down Chapel Street, where the crawl’s energy shifts toward an exotic finale at Jungle Boy.
Ending the night in a lush tropical retreat, Jungle Boy dazzles with bold tiki cocktails and vibrant greenery, delivering a dynamic, memorable finale bursting with social flair.
The next stop is the conclusion of the crawl — the perfect place to savor your last sip and reflect on an exhilarating night out.
From the first clink of a glass to the final tropical sip, this Windsor cocktail bar crawl is your ticket to an unforgettable night of vibrant vibes and adventurous flavors. Whether you're rallying friends or flying solo, these five Chapel Street gems promise a seamless flow of excitement, unique ambiances, and expertly crafted cocktails. Ready to claim your spot in Windsor’s buzzing nightlife? Grab your crew and dive into this spirited journey — every stop is a new thrill waiting to be discovered.
Crawl Map