đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant nightlife with our cocktail bar crawl! Visit five fantastic venues like Naughty Nancy's, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, Holy Grail, and Jungle Boy. From cosy ship-themed bars with plush couches and antique chairs to trendy plant-filled lounges serving tiki mugs, there's something for every cocktail lover. Whether you're into rum, tiki drinks, or classic cocktails, this crawl is your perfect night out in Windsor—fun, flavorful, and unforgettable!
Last updated: July 2025
Kick off your night in Windsor’s buzzing Chapel Street with an exhilarating cocktail bar crawl designed to thrill and delight at every turn. Begin amid the energetic buzz of Naughty Nancy’s, where live music and hearty flavors set a spirited tone. Glide next into the playful charm of Better Days, where nostalgic games and inventive cocktails spark fresh laughter and connection. The journey continues with Blackwoods, a polished yet welcoming spot that effortlessly blends sophistication with social ease. Then sail into the ship-themed allure of Holy Grail, where rum and craft cocktails come alive in a plush, conversation-friendly setting. Finally, plunge into the tropical oasis of Jungle Boy, where exotic sips in tiki mugs and lush greenery round out an unforgettable night. This crawl weaves together distinct moods and experiences, crafting an adventurous flow that keeps the energy rising and the good times rolling.
Launch your night with Naughty Nancy’s infectious energy—where live music pumps up the crowd and bold, food-forward flavors fuel the fun. This spot sets the pulse for the crawl with its vibrant atmosphere and craft cocktails.
The next stop is a brief, lively stroll down Chapel Street, keeping the energy high and anticipation building.
Step into Better Days for a playful twist with cozy couches, interactive games, and cocktails that spark smiles. Its inviting vibe offers a perfect contrast, turning up the social buzz and friendly competition.
The next stop is a quick, engaging walk along Chapel Street, maintaining the crawl’s rhythmic flow.
Elevate the night at Blackwoods, where expert mixology meets an elegantly approachable ambiance. This stop balances sophistication with warmth, ideal for savoring crafted cocktails among friends.
The next stop is a short, smooth walk continuing down Chapel Street, keeping momentum steady and anticipation growing.
Immerse yourself in the ship-themed charm of Holy Grail, where plush seating and expertly made rum cocktails create a relaxed yet spirited setting—perfect for lively conversations and group celebrations.
The next stop is a lively stroll just a few steps away, guiding you toward the crawl’s tropical finale.
Cap off your adventure at Jungle Boy’s tropical sanctuary, where vibrant plant life, unique tiki mugs, and bold cocktails deliver an exotic climax. This lush lounge invites you to revel in style and spirited fun.
The crawl concludes here—no more walking, just lingering in the jungle-inspired atmosphere.
Whether you’re a cocktail connoisseur or simply chasing a night packed with energy and discovery, this Windsor crawl delivers a seamless blend of flavors, moods, and social sparks. Each stop brings a fresh vibe and new reasons to raise your glass. Ready to chart your own course through Chapel Street’s cocktail treasures? Gather your crew, pace the night, and make every sip count on this unforgettable adventure.
Crawl Map