đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s best cocktail bars on this fun-filled crawl! Visit five unique venues like Three Monkeys, Better Days, Blackwoods, Holy Grail, and Jungle Boy. From ship-themed cozy spots with plush couches to plant-filled lounges serving tiki mugs, each bar offers a quirky, snug atmosphere perfect for a relaxed night out. Whether you’re into rum, cocktails, or lively DJ parties on weekends, this crawl has something for everyone looking to enjoy great drinks and good times in Windsor’s vibrant nightlife scene.
Last updated: July 2025
Embark on an electrifying cocktail journey through Windsor’s Chapel Street, where every bar offers a fresh twist on social adventure. Begin your night immersed in the vibrant energy of Three Monkeys, where lively beats and expertly mixed drinks set the tone. Then, spark playful competition at Better Days, where board games and nostalgic vibes keep the fun flowing. As the evening progresses, Blackwoods invites you to elevate the experience with elegant cocktails and a curated wine selection in a welcoming space. Slide into the cozy, ship-themed Holy Grail next, savoring rich rums and handcrafted drinks amid plush seating. Finally, cap off your crawl at Jungle Boy, a tropical oasis bursting with lush greenery and daring tiki cocktails, ensuring your night ends on a thrilling, unforgettable high. This crawl is your passport to Windsor’s most dynamic, flavour-packed nightlife adventure.
Start your night with Three Monkeys’ infectious energy where quirky charm meets weekend DJ vibes, igniting the perfect atmosphere for social buzz and creative cocktails.
The next stop is a quick, vibrant stroll down Chapel Street, keeping the energy high as you head to a bar famed for games and great drinks.
Here, the mood shifts into playful camaraderie with board games and inventive cocktails fueling laughter and friendly competition in a lively yet intimate setting.
The next stop is a brief, upbeat walk along Chapel Street, leading you deeper into Windsor’s cocktail heart for a taste of refined indulgence.
Blackwoods elevates the crawl with its polished yet inviting vibe, offering expertly balanced cocktails and a sophisticated wine list that adds a touch of elegance to the night.
The next stop is a comfortable, atmospheric walk down Chapel Street, transitioning smoothly into a uniquely themed bar where conversation flows effortlessly.
Step aboard Holy Grail’s ship-inspired sanctuary, where plush seating and an impressive rum selection create a cozy yet spirited setting for embracing the night’s deeper rhythms.
The next stop is a short, lively stroll that brings you to a tropical hideaway bursting with bold flavours and vibrant greens.
Conclude your adventure at Jungle Boy, a lush oasis of exotic cocktails served in iconic tiki mugs, wrapping up the crawl with a playful, tropical flourish that leaves spirits soaring.
The crawl ends here, giving you the perfect spot to savor your final drinks amid captivating jungle vibes.
This Windsor cocktail bar crawl is your ultimate ticket to an unforgettable night filled with vibrant atmospheres, innovative drinks, and engaging social moments. Whether you’re celebrating with friends or seeking new adventures, each stop offers a distinctive experience that builds on the last, crafting a seamless flow of excitement. So lace up your walking shoes, gather your crew, and dive headfirst into Windsor’s spirited cocktail scene — your next great night out starts here!
Crawl Map