đź“… Open Today: Crawl likely open on Fridays
Join us for an unforgettable cocktail bar crawl in Windsor! Explore five top spots, from snug, ship-themed bars with plush couches to lively neighbourhood hangouts with DJ parties on weekends. Whether you're into rum, tiki mugs, or craft cocktails, this crawl has it all. Visit iconic venues like Three Monkeys, Better Days, Blackwoods, Holy Grail, and Jungle Boy for a night filled with great drinks, cool vibes, and plenty of fun. Perfect for friends, date nights, or just a good time!
Last updated: July 2025
Embark on an electrifying cocktail bar crawl through Windsor’s buzzing Chapel Street, where every stop amps up the excitement and invites you into a new dimension of flavor and fun. Start your night at Three Monkeys, a spirited hotspot where infectious energy meets expertly mixed cocktails, setting the perfect tone. Slide into the playful world of Better Days, where classic board games and inventive drinks spark lively conversations and friendly competition. Next, elevate your evening at Blackwoods Wine & Cocktail Bar, a chic yet approachable venue blending sophisticated sips with a welcoming atmosphere. Navigate to Holy Grail’s captivating ship-themed retreat, where plush seating and a stellar rum collection invite you to unwind without losing the buzz. Cap off your adventure at Jungle Boy, a plant-filled tropical haven where exotic tiki cocktails and vibrant ambiance create an unforgettable finale. This crawl isn’t just a night out — it’s a dynamic journey through Windsor’s most exhilarating cocktail experiences, crafted for those ready to relish every spirited moment.
Launch your night at Three Monkeys, where a quirky, inviting atmosphere merges with upbeat weekend DJ vibes and expertly crafted cocktails to spark the evening’s lively momentum.
The next stop is a short, vibrant stroll down Chapel Street, keeping the energy fresh and anticipation high.
Step into Better Days for a playful shift—board games, nostalgic decor, and inventive cocktails create a social playground where laughter and friendly competition flow freely.
The next stop is an easy walk along Chapel Street, maintaining the crawl’s upbeat rhythm and inviting new discoveries.
Blackwoods elevates the experience with polished cocktails and a curated wine list, offering a sophisticated yet approachable vibe that fuels lively conversation and group celebrations.
The next stop is a brief, energizing walk deeper into Chapel Street, guiding you smoothly to a captivating new scene.
Immerse yourself in Holy Grail’s ship-themed sanctuary, where plush seating and a rich rum selection create an engaging setting for relaxed chats without dimming the night’s vibrant pulse.
The next stop is a lively stroll along Chapel Street, setting the stage for a tropical finale.
Conclude your adventure at Jungle Boy, a lush, plant-filled lounge where exotic tiki cocktails and a vibrant, intimate atmosphere spark an unforgettable last chapter to the crawl.
This is the final stop, perfect for settling in and savoring the night’s last exhilarating moments.
From the first clink of a cocktail glass to the final sip in a tropical hideaway, this Windsor cocktail crawl is your passport to a night packed with flavor, fun, and unforgettable connections. Whether you’re a cocktail connoisseur or a social adventurer, Chapel Street’s dynamic lineup of bars guarantees a night brimming with energy and discovery. Ready to take on Windsor’s spirited cocktail scene? Gather your crew, hit the streets, and let the night unfold one thrilling stop at a time.
Crawl Map