đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our curated bar crawl! Visit five fantastic venues, from cozy ship-themed bars with rum and cocktails to trendy plant-filled lounges serving tiki mugs. Enjoy a mix of snug atmospheres, quirky neighbourhood hangouts, and lively DJ parties on weekends. Whether you're after plush couches, antique chairs, or exposed-brick charm, this crawl offers a perfect blend of fun, flavor, and funky vibes for your unforgettable night out in Windsor.
Last updated: July 2025
Dive into Windsor’s dynamic cocktail scene with a bar crawl designed to electrify your evening and spark unforgettable social moments. Starting with the infectious energy of Three Monkeys’ weekend DJ sessions, this adventure unfolds through a mix of playful, stylish, and inviting venues. From the nostalgic game nights at Better Days to the elegant yet approachable ambiance of Blackwoods, every stop introduces a fresh vibe and bold flavors. The journey continues with the ship-themed charm of Holy Grail, where rum takes center stage, before culminating at Jungle Boy’s lush, tropical lounge filled with imaginative tiki cocktails. This crawl is your passport to an exhilarating night out where every sip fuels the next story.
Launch your night with Three Monkeys, a spirited hotspot where vibrant DJ beats and expertly mixed cocktails set the tone for a lively social adventure.
The next stop is a quick, upbeat stroll down Chapel Street, keeping the energy flowing as you head to Better Days Cocktail Bar.
Step into Better Days for a playful mix of inventive cocktails and classic board games, a perfect blend of fun and flavor that amps up the night’s camaraderie.
The next stop is a brief walk along Chapel Street, gently shifting the vibe toward a sophisticated yet welcoming atmosphere at Blackwoods.
Blackwoods offers a seamless mix of expertly curated wines and cocktails, creating an elegant yet vibrant setting that elevates the evening’s momentum.
The next stop is a short, anticipation-building walk to Holy Grail, where thematic charm and rich rum selections await.
Immerse yourself in Holy Grail’s ship-inspired décor and plush seating as you savor rum-forward cocktails, offering a perfect balance of spirited energy and cozy conversation.
The next stop is a lively walk down Chapel Street, leading into the lush, tropical ambiance of Jungle Boy.
Cap off the crawl at Jungle Boy, where exotic tiki mugs, vibrant greenery, and innovative cocktails create a festive finale bursting with tropical flair and adventurous spirit.
The next stop is the end of the crawl, leaving you perfectly positioned to continue your night in Windsor’s buzzing nightlife district.
This Windsor Cocktail Bar Crawl invites you to embrace the city’s eclectic nightlife, swapping stories over signature drinks and discovering the unique personality each venue brings. Whether you’re rallying a crew or flying solo, this adventure promises an energizing mix of music, flavor, and social sparks. Ready your taste buds and your dancing shoes — Windsor’s cocktail scene is calling.
Crawl Map