đź“… Open Today: Crawl likely open on Fridays
Join us on a vibrant Windsor cocktail bar crawl through five fantastic venues! Explore quirky hangouts like Three Monkeys and Jungle Boy, chill in plush, ship-themed spots with rum and cocktails, or groove to DJ parties at Better Days. Whether you're into cozy, plant-filled lounges or lively nightclubs, this crawl has it all. Perfect for a fun night out with friends, soaking up Windsor’s best bars, vibes, and unforgettable sips!
Last updated: July 2025
Kick off a thrilling night out in Windsor with a cocktail bar crawl that fuses creative mixology, dynamic atmospheres, and social buzz into one epic journey. Starting at Three Monkeys, you’ll dive into a spirited setting pulsing with weekend DJ energy and quirky charm. The adventure then shifts to Better Days Cocktail Bar, where nostalgia meets inventive drinks alongside games that spark friendly competition. Next, Blackwoods Wine & Cocktail Bar heightens the scene with its polished yet lively ambiance, setting the tone for an elegant yet vibrant evening. Holy Grail brings a unique twist with its ship-inspired décor and expertly crafted rum cocktails, perfect for intimate conversations or group celebrations. Finally, Jungle Boy closes the crawl with tropical flair—lush greenery, tiki mugs, and standout cocktails make it a lush finale to an unforgettable night. This crawl delivers a seamless progression of energy and style, ensuring every stop surprises and delights.
Launch your night at Three Monkeys, where lively DJ beats energize a quirky, intimate space perfect for fueling the crawl with expertly crafted cocktails and an infectious buzz.
The next stop is a short, easy stroll along Chapel Street, keeping the momentum high as you head into a playful and nostalgic atmosphere.
Step into Better Days, a vibrant hub of friendly competition and inventive drinks where retro games and eclectic vibes amplify the social adventure.
The next stop is a quick, lively walk down Chapel Street, setting the stage for a seamless transition into a refined yet spirited setting.
Elevate the evening at Blackwoods, where a curated wine list and polished cocktails meet a bustling yet elegant ambiance, perfect for deepening connections as energy builds.
The next stop is a brief, engaging walk further along Chapel Street, inviting anticipation for the crawl’s thematic shift toward quirky sophistication.
Immerse yourself in Holy Grail’s ship-themed sanctuary where plush seating and expertly made rum cocktails offer a spirited yet conversational vibe, ideal for groups or intimate celebrations.
The next stop is a swift stroll down Chapel Street, perfectly timed to refresh the atmosphere with a burst of tropical energy.
Cap off the night at Jungle Boy, a lush tropical oasis where vibrant greenery and innovative tiki cocktails create an energetic and exotic finale to your Windsor adventure.
The crawl concludes here, so no further walking is needed—just settle in and savor the final waves of excitement.
This Windsor Cocktail Bar Crawl delivers an electrifying journey through Chapel Street’s top cocktail destinations. Each stop pulses with its own unique energy, creating a dynamic night full of discovery, laughter, and exceptional drinks. Whether you’re rallying friends or meeting new faces, this crawl guarantees a memorable, adventure-packed evening. Ready to shake up your night? Grab your crew, hit the crawl, and let Windsor’s spirited cocktail scene ignite your senses!
Crawl Map