đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our curated bar crawl! Visit five unique spots, from snug, ship-themed bars with plush couches to plant-filled lounges serving tiki mugs. Whether you're into rum, creative cocktails, or weekend DJ parties, this crawl has it all. Sample the best drinks at venues like Three Monkeys, Better Days, Blackwoods, Holy Grail, and Jungle Boy. Perfect for a relaxed, fun night out with friends in a friendly, lively atmosphere!
Last updated: July 2025
Kick off your night in Windsor with a cocktail crawl that pulses with energy, creativity, and social spark. This carefully curated route along Chapel Street takes you from intimate, quirky venues to lush tropical lounges, each offering expertly crafted cocktails and a unique atmosphere. Begin at a hotspot known for its weekend DJ parties, then glide into a playful bar filled with board games and nostalgic vibes. The journey continues through elegantly unpretentious wine and cocktail spots before sailing into a ship-themed hideaway perfect for sharing laughs and rum. Cap it all off at a jungle-inspired lounge where bold tiki creations and verdant surroundings set the stage for a night of memorable adventures. Whether you’re out with friends or diving solo, this crawl delivers a dynamic flow of fun and flavor that embodies Windsor’s spirited nightlife.
Launch your crawl at Three Monkeys, where intimate vibes meet infectious energy. With quirky décor and weekend DJ sessions, this spot gets the party started with expertly crafted cocktails and a welcoming buzz that sparks lively conversations and sets a high-spirited tone.
The next stop is a short, spirited stroll down Chapel Street to Better Days Cocktail Bar, perfect for keeping the night’s momentum flowing.
Step into Better Days for a vibrant mix of nostalgia and playfulness. This lively playground of board games, retro video screens, and inventive cocktails invites you to unwind while staying engaged—ideal for deepening connections or sparking new ones within its upbeat, social atmosphere.
The next stop is an easy, upbeat walk further along Chapel Street to Blackwoods Wine & Cocktail Bar, shifting the vibe toward elegant yet approachable sophistication.
Blackwoods elevates the night with a refined yet inviting environment. Here, sparkling wine selections and masterfully mixed cocktails create the perfect backdrop for vibrant conversations and group celebrations, offering a dynamic but polished transition as the evening unfolds.
The next stop is a brief and lively walk to Holy Grail, where the scene turns intriguingly thematic and intimate.
Step aboard Holy Grail, a ship-themed sanctuary where plush seating and antique touches create a cozy yet spirited space. The bar’s skilled cocktail crafting and extensive rum selection invite you to linger, sharing stories over delicious bites and expertly mixed drinks in an atmosphere that balances intimacy with festive flair.
The next stop is a short, exciting walk to Jungle Boy, where the vibe shifts to a tropical, lush finale.
Conclude your crawl immersed in Jungle Boy’s verdant, tiki-inspired lounge. With exotic cocktails served in distinctive mugs and a vibrant yet polished atmosphere, this spot delivers a thrilling tropical escape—perfect for raising the final toast and savoring the adventurous spirit of Chapel Street’s nightlife.
The next stop is wherever the night takes you—Jungle Boy’s lively energy makes it a fitting finale for this unforgettable crawl.
From the spirited beats of Three Monkeys to the lush escapes of Jungle Boy, this Windsor cocktail crawl delivers a night packed with diverse flavors, lively atmospheres, and memorable moments. Whether you’re chasing bold new cocktails or craving vibrant social scenes, Chapel Street’s best bars await your discovery. Ready for your next great night out? Lace up your walking shoes and dive into Windsor’s electrifying cocktail adventure!
Crawl Map