đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant cocktail scene with our exclusive crawl through five fantastic venues. From the cosy ship-themed Three Monkeys to the lush, plant-filled Jungle Boy, each spot offers unique vibes—whether you're after rum, creative cocktails, or weekend DJ parties. Perfect for those who love quirky neighbourhood hangouts with plush couches, antique chairs, and lively atmospheres. Get ready for a night of good drinks, great company, and unforgettable memories!
Last updated: July 2025
Dive headfirst into Windsor’s vibrant nightlife with this energetic cocktail bar crawl along Chapel Street. From the infectious rhythms and intimate charm of Three Monkeys to the playful spirit and inventive mixes at Better Days Cocktail Bar, this crawl sets a lively tone from the get-go. As you progress, Blackwoods Wine & Cocktail Bar offers a stylish yet approachable scene, perfect for elevating the evening with expertly crafted cocktails and fine wines. The journey continues to Holy Grail, where a ship-inspired sanctuary invites you to savor rich rums and unwind in plush, vintage surroundings. Culminate your night at Jungle Boy, a lush tropical oasis alive with exotic flavors and spirited vibes. Each stop is carefully chosen to elevate your social adventure, creating a seamless flow from upbeat beginnings to memorable finales. Get ready to sip, savor, and socialize your way through Windsor’s most thrilling cocktail destinations.
Kick off the crawl with Three Monkeys’ quirky charm and infectious energy, where expertly crafted cocktails meet vibrant DJ beats, setting an exciting tone for the night ahead.
The next stop is a short, lively stroll down Chapel Street, keeping the momentum going as you head toward Better Days Cocktail Bar.
Step into a playful atmosphere filled with nostalgic board games and inventive cocktails, perfect for sparking fun conversations and friendly competition as the night heats up.
The next stop is just a brief walk along Chapel Street, maintaining the energetic vibe as you continue your cocktail adventure to Blackwoods.
Elevate your experience with Blackwoods’ elegant yet inviting ambiance, where refined cocktails and a curated wine selection fuel lively chats and sophisticated fun.
The next stop is a quick, smooth walk that shifts the scene toward the nostalgic maritime charm of Holy Grail.
Immerse yourself in the cozy, ship-themed surroundings of Holy Grail, where plush seating and an impressive rum selection invite deep conversations and group camaraderie.
The next stop is a short stroll down Chapel Street, ushering in the tropical finale at Jungle Boy.
Cap off the crawl with Jungle Boy’s exotic plant-filled lounge, where tiki mugs overflow with adventurous cocktails and the vibrant atmosphere keeps the night alive.
The crawl concludes here, leaving you perfectly positioned to continue your night or call it a memorable evening.
This Windsor cocktail bar crawl delivers an unforgettable journey through Chapel Street’s most dynamic and spirited spots. Whether you’re chasing inventive cocktails, immersive atmospheres, or lively social scenes, each stop adds its unique flavor to an evening packed with energy and adventure. Gather your crew, lace up your walking shoes, and let this curated route ignite your night with bold drinks and vibrant connections. Ready, set, sip!
Crawl Map