đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our fun-filled crawl through 5 unique venues. From cosy ship-themed bars with plush couches and antique chairs to trendy plant-filled lounges serving tiki mugs, this tour has it all. Visit hotspots like Naughty Nancy's, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, Holy Grail, and Jungle Boy for an unforgettable night of rum, cocktails, and good vibes. Perfect for anyone looking to explore Windsor’s best drinking spots with friends!
Last updated: July 2025
Kick off your Windsor night with an exhilarating cocktail journey along Chapel Street that promises more than just drinks — it’s a social adventure packed with energy and creativity. Begin at Naughty Nancy’s, where the pulsating rhythm of live music and bold food flavors set the tone for an unforgettable evening. Next, dive into the playful spirit at Better Days, mixing nostalgic games with inventive cocktails that spark laughter and connection. As the night deepens, Blackwoods offers an elegant yet lively pause with expertly crafted cocktails and a welcoming buzz ideal for sparking conversation. Then, sail into the cozy, ship-inspired Holy Grail, where smooth rums and hand-mixed drinks invite camaraderie and warmth. Finally, cap off your crawl at Jungle Boy, an exotic urban oasis where tropical cocktails and lush greenery elevate your night to spirited heights. Each stop builds upon the last, crafting a dynamic arc of excitement, flavor, and social vibes you won’t want to end.
Launching the crawl with bold energy, Naughty Nancy’s blends lively live music with hearty, flavor-packed eats and inventive cocktails, igniting the night with a vibrant buzz.
The next stop is a brisk, engaging stroll along Chapel Street, just a few minutes away to Better Days Cocktail Bar.
Better Days shifts the vibe into playful gear with cozy couches, nostalgic video games, and a lineup of inventive cocktails, turning the night into a social playground.
The next stop is a short, lively walk down Chapel Street to Blackwoods Wine & Cocktail Bar, keeping the momentum rolling.
Blackwoods raises the bar with sophisticated yet spirited cocktails and a crowd-pleasing wine list, delivering a polished atmosphere that balances elegance with vibrant energy.
The next stop is a convenient stroll along the bustling street, leading you to the ship-themed Holy Grail, where warmth awaits.
Holy Grail invites you aboard its cozy, ship-inspired setting where expertly crafted cocktails and a rich rum selection create an intimate yet lively haven for groups and conversations.
The next stop is a short walk along Chapel Street to Jungle Boy, your tropical cocktail escape to end the night.
Jungle Boy closes out the crawl with a burst of tropical flair and lush greenery, serving standout tiki-style cocktails in a vibrant, stylish lounge that sparks festive spirit.
The next stop is the end of the crawl—no walk needed, just dive into the lively atmosphere and savor the final cocktails.
Ready to turn your night into a whirlwind of vibrant flavors, contagious energy, and memorable connections? This Windsor cocktail crawl along Chapel Street is your ticket to a night packed with expertly crafted drinks and dynamic atmospheres. Gather your crew, pace yourself through these unique hotspots, and let each bar elevate your adventure. Whether you're a cocktail connoisseur or a night seeker craving fresh vibes, this crawl promises a lively, social escapade you’ll be talking about long after last call.
Crawl Map