đź“… Open Today: Crawl likely open on Fridays
Join us for an unforgettable cocktail bar crawl in Windsor! Explore five fantastic venues, from the snug, ship-themed Three Monkeys to the plant-filled Jungle Boy. Sip on creative cocktails, enjoy DJ parties on weekends, and soak up the lively, quirky neighbourhood atmosphere. Whether you're into rum, tiki mugs, or plush couches, this crawl has something for every cocktail lover. Perfect for a fun night out with friends in Windsor’s vibrant bar scene!
Last updated: July 2025
Windsor’s Chapel Street pulses with energy, and this cocktail bar crawl is your passport to an evening packed with flavor, fun, and unforgettable social moments. Kick off the night at Three Monkeys, where infectious laughter and weekend DJ vibes set a buzzing tone. Then, power up your playfulness at Better Days, a cozy spot blending retro games with inventive cocktails that spark connections. Next, elevate the mood at Blackwoods Wine & Cocktail Bar, a polished yet inviting space where craft drinks and curated wines flow freely. As the night deepens, Holy Grail’s ship-inspired charm and expertly mixed rums invite you to linger over intimate conversations or lively group cheers. Finally, cap off your journey at Jungle Boy, where tropical greenery and daring tiki cocktails create a lush, exhilarating finale. This crawl weaves together contrasts and complements, ensuring every step pulses with fresh excitement and social adventure.
Launch your adventure at Three Monkeys, where a quirky, intimate setting and weekend DJ beats spark lively conversations and set an energetic pace for the night.
The next stop is a brief stroll down Chapel Street, keeping the energy up as you step into a more playful, game-filled vibe.
Better Days amps the fun with retro video games and inventive cocktails, inviting you to let loose and share laughter in a warmly charged atmosphere.
The next stop is just a short walk further along Chapel Street, shifting the scene toward cocktail craftsmanship and refined socializing.
Here, the crawl takes on a polished edge with elegantly crafted cocktails and a curated wine list, perfect for savoring flavor while mingling with a sophisticated crowd.
The next stop is a quick and easy walk nearby, transitioning you into a cozy, themed haven with rich character and rum-forward creations.
Step aboard Holy Grail’s ship-inspired interior to enjoy plush seating and expertly mixed cocktails, where the vibe invites both lively group cheers and intimate chats.
The next stop is a lively walk that brings you into a lush, tropical escape filled with vibrant flavors and exotic charm.
Conclude your journey at Jungle Boy, where exposed brick and greenery create a spirited oasis for adventurous tiki cocktails and memorable moments that linger long after last call.
This final stop wraps the crawl, leaving you perfectly poised to reflect on an electrifying night or continue your Windsor exploration.
This Windsor cocktail bar crawl is more than a night out—it’s an energetic expedition through some of Chapel Street’s most vibrant and character-rich watering holes. From infectious beats and playful nostalgia to polished cocktails and tropical twists, each stop builds on the last, crafting an unforgettable social adventure. Ready to sip, savor, and socialize your way through Windsor? Gather your crew and dive into this thrilling crawl that promises elevated drinks, electric atmospheres, and memories made one cocktail at a time.
Crawl Map