đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our curated bar crawl! From snug, ship-themed spots serving rum and cocktails in plush surrounds to plant-filled lounges with tiki mugs, you’ll visit 5 unique venues including Three Monkeys, Better Days, Blackwoods, Holy Grail, and Jungle Boy. Whether you’re after quirky neighbourhood hangouts or lively DJ nights, this crawl offers a fun, friendly way to enjoy Windsor’s best bars and create memorable nights out!
Last updated: July 2025
Windsor’s Chapel Street pulses with a cocktail culture that’s anything but ordinary. This crawl is your ticket to a night bursting with flavor, energy, and social sparks. Begin your adventure at Three Monkeys, where quirky charm and weekend DJ vibes set the tone. Next, dive into playful competition and inventive drinks at Better Days Cocktail Bar. Elevate the evening with the refined yet lively atmosphere of Blackwoods Wine & Cocktail Bar before settling into the ship-inspired warmth of Holy Grail, where rum takes center stage. Finally, cap off the night at Jungle Boy, a tropical sanctuary serving bold tiki cocktails amid lush greenery. Each stop offers a distinct vibe, crafting a pulse-pounding journey through Windsor’s most spirited cocktail destinations.
Kick off your Windsor cocktail adventure at Three Monkeys, where quirky interiors and weekend DJ energy create the perfect launchpad for an electrifying night. Their expertly mixed drinks and vibrant atmosphere invite immediate connection and celebration.
The next stop is a brief, lively stroll down Chapel Street, keeping the buzz alive as you head to Better Days Cocktail Bar.
Better Days injects a playful spirit into the crawl with its cozy couches, nostalgic board games, and inventive cocktails. It’s the ideal pit stop to spark friendly competition and deepen the night’s social energy.
The next stop is a short, engaging walk further along Chapel Street, keeping the vibrant momentum pulsing toward Blackwoods Wine & Cocktail Bar.
At Blackwoods, the crawl takes on a polished edge with an expertly curated cocktail and wine selection. This stop perfectly balances sophistication with warmth, elevating the night’s vibe as conversations deepen and glasses clink.
The next stop is a comfortable stroll along the lively Chapel Street, transitioning the vibe towards the inviting, ship-themed Holy Grail.
Holy Grail anchors the middle of the crawl with its plush, ship-inspired setting and rich rum selection. The approachable yet stylish atmosphere encourages relaxed mingling and sets the stage for a memorable night ahead.
The next stop is a quick walk along Chapel Street, where the tropical allure of Jungle Boy awaits to uplift the final leg of your adventure.
Conclude your crawl at Jungle Boy, a lush, plant-filled lounge pulsating with tiki vibes and daring cocktails. The exotic setting and bold flavors provide the perfect crescendo to an unforgettable night of social adventure and spirited fun.
This is the final stop, so no further walking is needed—just soak in the vibrant tropical energy and celebrate your Windsor cocktail journey.
From quirky beginnings to tropical finales, this Windsor cocktail bar crawl is designed to keep your night buzzing with fresh flavors and dynamic social scenes. Whether you're out with friends or making new ones along the way, each venue offers a new chapter of excitement. So lace up your walking shoes, bring your sense of adventure, and let Chapel Street’s cocktail gems guide your spirited exploration. Ready to sip, savor, and socialize your way through Windsor? The night is yours.
Crawl Map