đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's best cocktail bars on our fun-filled crawl! Explore five fantastic spots, from cozy ship-themed rum bars with plush couches to vibrant, plant-filled tiki lounges serving creative cocktails. Whether you're into classic pub vibes or trendy nightclubs, this crawl has it all—Naughty Nancy's, Better Days, Blackwoods, Holy Grail, and Jungle Boy. Perfect for friends looking for a memorable night out with great drinks, lively atmosphere, and good vibes!
Last updated: July 2025
Dive headfirst into the dynamic pulse of Windsor’s Chapel Street with our curated cocktail bar crawl designed for thrill-seekers and social adventurers. This journey kicks off amid the infectious energy of Naughty Nancy’s, where live music and bold flavors set the tone. Next, shift gears to Better Days Cocktail Bar, blending nostalgic fun with inventive drinks that spark laughter and connection. As the night flows, Blackwoods Wine & Cocktail Bar offers a polished yet lively spot to savor masterful cocktails and fine wines. Then, step aboard the ship-inspired Holy Grail, where rich rums and cozy corners invite spirited conversations. Finally, lose yourself in the tropical oasis of Jungle Boy, where exotic cocktails in tiki mugs and lush greenery create an unforgettable finale. Each stop builds on the last, crafting a night full of surprises, vibrant vibes, and exceptional drinks—ready to awaken your senses and ignite your social spirit.
Kick off your crawl amid the lively buzz of Naughty Nancy’s, where live music fuels an energetic atmosphere and hearty, flavor-packed dishes keep the momentum going strong.
The next stop is a short, vibrant stroll down Chapel Street where anticipation builds for a playful change of pace.
Transition to Better Days, a spirited spot where inventive cocktails meet nostalgic board games, perfect for sparking laughter and lively connections in a cozy yet upbeat setting.
The next stop is a brisk walk continuing along Chapel Street, setting the stage for a more refined cocktail experience.
Elevate the night at Blackwoods, where expert mixology and a curated wine list create a lively yet polished ambiance—ideal for savoring sophisticated flavors with friends.
The next stop is a comfortable stroll just down the street, inviting you to step aboard a unique thematic experience.
Immerse yourself in the ship-themed charm of Holy Grail, where plush seating and a stellar selection of rums set the mood for engaging conversations and spirited drink discoveries.
The next stop is a lively walk along Chapel Street, guiding you toward a lush tropical retreat to round out the night.
Cap off your adventure in the vibrant, plant-filled lounge of Jungle Boy, where exotic cocktails served in tiki mugs and an energized atmosphere promise a memorable finale.
The crawl concludes here, with easy access back to Windsor’s main streets for onward evening plans.
From the first lively note at Naughty Nancy’s to the tropical crescendo at Jungle Boy, this Windsor cocktail bar crawl delivers an unforgettable night packed with diverse vibes, expertly crafted drinks, and endless social energy. Whether you’re rallying friends or flying solo, these five Chapel Street gems promise a spirited adventure that redefines your night out. Ready to sip your way through Windsor’s best? Grab your crew, follow the trail, and let the good times roll!
Crawl Map