đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s best cocktail bars on this lively crawl through four unique venues! From the snug, ship-themed Blackwoods to the quirky Better Days and the vibrant Holy Grail, each spot offers a perfect mix of rum, cocktails, and cosy vibes. Whether you're after a relaxed night with plush couches or a dancefloor filled with weekend DJ beats, this crawl has it all. Perfect for friends, fun, and unforgettable nights out in Windsor!
Last updated: July 2025
Kick off your night in Windsor with a cocktail bar crawl that crackles with energy and social buzz. This curated journey along Chapel Street is designed for those who seek dynamic atmospheres, expert mixology, and a lively crowd. Begin at Three Monkeys, where an infectious soundtrack and quirky charm set a spirited tone. Then, slide into Better Days for a playful twist—think board games and inventive cocktails sparking laughter and connection. Next, embrace a sophisticated yet vibrant mood at Blackwoods, a hotspot where expertly crafted drinks meet a welcoming crowd. Finally, sail into the cozy, ship-themed Holy Grail, where rum flows freely and the atmosphere invites deep conversations and celebration. This crawl pulses with excitement and variety, promising an adventurous night brimming with fun and unforgettable moments.
Launching the crawl with an energetic buzz, Three Monkeys serves as the perfect kickoff point. Its lively DJ sets and expertly mixed cocktails create a vibrant, social playground that gets the night’s momentum flowing.
The next stop is a quick, upbeat stroll down Chapel Street, keeping the energy alive as you head towards the playful ambiance of Better Days.
Better Days amps up the social adventure with its fusion of inventive cocktails and interactive fun. The mix of cozy couches and gaming screens adds a lively, adventurous spirit, perfect for sparking connections.
The next stop is a short, vibrant walk along Chapel Street, letting you carry the buzzing energy forward to a more refined yet equally dynamic setting at Blackwoods.
Blackwoods shifts the vibe into an elegant groove without losing the night’s vivacity. With a balance of artfully crafted cocktails and a curated wine list, it’s the ideal spot for those who want sophistication with a lively pulse.
The next stop is a brief and welcoming walk down Chapel Street, preparing you to dive into the cozy yet spirited atmosphere of Holy Grail.
Holy Grail caps the crawl with its unique ship-themed charm and expertly poured rums, offering plush seating for animated conversations and a festive finale that keeps the night’s adventurous vibe sailing strong.
The crawl concludes here, making this stop the perfect spot to linger, celebrate, and toast to an unforgettable Windsor night.
Your Windsor Cocktail Bar Crawl ends on a high note at Holy Grail, but the night’s energy is yours to carry forward. Whether you choose to explore more of Chapel Street’s nightlife or relive the memories of expertly crafted cocktails and new friendships, this crawl delivers an exhilarating adventure from start to finish. Ready to taste Windsor’s finest, meet new faces, and make the night legendary? Grab your crew and let the cocktails—and good times—flow!
Crawl Map