đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant cocktail scene with our exclusive bar crawl! Visit five unique venues, from the snug, ship-themed Three Monkeys with plush couches to the plant-filled Jungle Boy serving tiki mugs. Enjoy quirky neighbourhood hangouts, creative cocktails, and weekend DJ parties that keep the energy high. Whether you're after cozy corners or lively tunes, this crawl is your ticket to a fun-filled night out in Windsor’s coolest spots. Cheers to great drinks and even better company!
Last updated: July 2025
Kick off an electrifying night on Windsor’s iconic Chapel Street with a cocktail crawl that pulses with energy and adventurous spirit. This handpicked journey moves through a spectrum of vibrant venues—from quirky neighborhood gems to sleek lounges—each offering masterful drinks and immersive atmospheres. Whether you're sparking up conversations with new friends or celebrating with your crew, every stop is designed to elevate your night with signature cocktails, engaging vibes, and a buzz that keeps you moving. Get ready to explore Windsor's cocktail culture where every sip fuels a lively social adventure.
Start your crawl at Three Monkeys, a spirited hub where quirky charm meets expertly crafted cocktails and weekend DJ beats, igniting the night with infectious energy and intimate social buzz.
The next stop is a short and lively stroll down Chapel Street, maintaining the vibrant street-side energy as you transition into a playful, game-filled social hotspot.
Dive into Better Days’ playful ambiance, where inventive cocktails and nostalgic board games spark laughter and connection, turning up the fun factor and setting a lively social tone.
The next stop is a brisk walk along Chapel Street, shifting the vibe toward a refined yet buzzing scene ready to welcome you with expertly balanced cocktails.
Elevate the evening at Blackwoods, where a polished yet approachable atmosphere blends creative cocktails with a curated wine list—perfect for raising your glass in style amid friendly chatter.
The next stop is a short, engaging walk through Chapel Street’s vibrant pulse, preparing you for a thematic shift to cozy, ship-inspired surroundings with a spirited rum focus.
Settle into the plush, ship-themed Holy Grail, where handcrafted cocktails and a fine rum selection create an inviting yet lively refuge, blending comfort with spirited conversations and shared bites.
The next stop is a quick, upbeat walk along Chapel Street, transitioning the vibe into a lush, tropical retreat that promises exotic flavors and vibrant cocktails.
Conclude your crawl at Jungle Boy, a tropical sanctuary pulsing with energy—lush greenery, daring tiki cocktails, and a convivial atmosphere that caps the night with unforgettable flair and fun.
The next stop is the wrap-up of the crawl; here, the lively energy peaks, making Jungle Boy the perfect final destination for a tropical cocktail celebration.
From the quirky beats of Three Monkeys to the tropical crescendo at Jungle Boy, this Windsor cocktail bar crawl delivers an unforgettable night of spirited exploration and social connection. Whether you’re a cocktail connoisseur or a night owl chasing vibrant vibes, this route promises fresh flavors, dynamic atmospheres, and endless chances to mingle. Grab your friends, dress to impress, and set out on a Chapel Street adventure that turns every glass into a celebration. Cheers to your next great night out in Windsor!
Crawl Map