đź“… Open Today: Crawl likely open on Fridays
Ready for a night of sipping and socialising? Explore Windsor’s vibrant cocktail scene with our curated crawl featuring 5 fantastic venues. From cozy, ship-themed bars serving rum and creative cocktails to trendy tiki mug lounges filled with fresh plant decor, this crawl has it all. Enjoy plush couches, antique chairs, and lively atmospheres at spots like Naughty Nancy's, Better Days, Blackwoods, Holy Grail, and Jungle Boy. Perfect for cocktail lovers and night owls alike!
Last updated: July 2025
Set foot on Chapel Street for an electrifying cocktail bar crawl that pulses with energy, flavor, and social buzz. This carefully curated route kicks off where hearty pub eats meet live tunes, then flows into cozy spots loaded with playful games and inventive drinks. As the night unfolds, expect a seamless shift to elegant cocktail craftsmanship, followed by a cosy, ship-inspired rum sanctuary. The adventure culminates in a lush, tropical lounge where tiki mugs and exotic concoctions reign supreme. Each stop offers its own unique vibe, creating a dynamic journey through Windsor’s most exciting cocktail destinations — perfect for friends eager to explore, laugh, and toast to unforgettable nights.
Kickoff your night amid the vibrant buzz of Naughty Nancy’s where craft cocktails and live music set a high-energy tone, pairing lively rhythms with bold, flavor-packed eats that fuel your social adventure.
The next stop is a quick and easy stroll down Chapel Street, keeping the energy flowing as you head to a bar that blends playful vibes with creative cocktails.
Here, the atmosphere turns playfully interactive with board games and nostalgic video games, offering a lively yet intimate setting where inventive cocktails spark laughter and shared moments.
The next stop is a short walk along the buzzing street, guiding you towards a spot that balances spirited socializing with sophisticated sips.
Elevate the experience with Blackwoods’ expertly crafted cocktails and curated wines, where polished yet unpretentious vibes create the perfect backdrop for engaging conversations or group celebrations.
The next stop is just a brief walk along Chapel Street, inviting you into a warmly themed bar with a distinct maritime twist.
Step aboard Holy Grail, a ship-inspired haven where plush seating and attentive service pair perfectly with masterfully mixed rum cocktails, setting a relaxed yet vibrant scene for deeper connections and lively chats.
The next stop is a short walk along the street, leading you to a vibrant tropical oasis that caps off the night with flair.
Conclude your journey surrounded by lush greenery and exotic tiki cocktails at Jungle Boy, where adventurous flavors and stylish ambiance invite you to celebrate the night’s finale in spirited tropical style.
The crawl ends here, leaving you perfectly poised to either keep the party going or savor the last vibrant moments of your Windsor adventure.
This Windsor cocktail bar crawl is your passport to an unforgettable night brimming with diverse vibes, inventive drinks, and social energy that never quits. From lively live music to tropical escapes, each stop raises the bar on excitement and camaraderie. Gather your crew, hit Chapel Street, and let this dynamic lineup of bars turn your evening into a spirited celebration of Windsor’s cocktail culture. Ready to dive in? The adventure awaits—with great drinks and even better company just steps away.
Crawl Map