đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our exclusive bar crawl! Visit four awesome venues including Three Monkeys, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, and Holy Grail. Each spot offers a cosy, ship-themed vibe, plush couches, and a lively atmosphere with DJ parties on weekends. Perfect for anyone looking to enjoy rum, cocktails, and good times in a friendly, quirky neighbourhood. Grab your friends and let's make it a night to remember!
Last updated: July 2025
Embark on a spirited journey through Windsor’s Chapel Street, where each stop amps up the excitement and invites social adventure. This cocktail bar crawl starts with the pulsing rhythms and infectious energy of Three Monkeys, setting a lively tone. Next, dive into playful nostalgia and inventive mixes at Better Days Cocktail Bar, where games spark laughter and new connections. The momentum builds at Blackwoods Wine & Cocktail Bar, offering sophisticated sips in an elegantly welcoming setting perfect for raising a toast. Finally, the crawl anchors at the captivating Holy Grail, a ship-inspired sanctuary blending classic rums and cozy camaraderie to cap the night. This crawl isn’t just about drinks—it’s a vibrant story of Windsor’s buzzing nightlife, designed to keep the energy flowing and the good times rolling.
Launching the night with infectious energy, Three Monkeys sets the pace with dynamic beats and expertly crafted cocktails, creating a lively hub to spark conversation and celebration.
The next stop is a quick and engaging stroll down Chapel Street, keeping the night’s momentum alive as you head toward a playful and inviting atmosphere.
Better Days injects fun and nostalgia into the crawl, where inventive cocktails meet classic games—perfect for sparking friendly competition and shared laughter amid the social buzz.
The next stop is just a short, energetic walk along Chapel Street, transitioning seamlessly to a setting that balances refined vibes with approachable charm.
Blackwoods elevates the experience with a polished yet welcoming scene, where masterful cocktail craftsmanship and a curated wine selection invite deeper connections and spirited toasts.
The next stop is a brief stroll down Chapel Street, shifting the vibe towards an intimate, themed venue that promises a memorable finale.
Holy Grail anchors the crawl with its ship-inspired charm and plush seating, offering expertly mixed rum cocktails in a space designed for conviviality and relaxed good times as the night deepens.
The next stop marks the end of this spirited journey—here, the night settles into memorable moments and lasting stories.
From the electrifying beats at Three Monkeys to the cozy nautical charm of Holy Grail, this Windsor cocktail crawl is your ticket to an unforgettable night of discovery and delight. Gather your crew, embrace the vibrant energy, and let Chapel Street unveil its spirited secrets one cocktail at a time. Ready to toast your next adventure? The night is calling.
Crawl Map