đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our curated bar crawl! Explore five fantastic venues including the ship-themed Three Monkeys, the plush Better Days, the plant-filled Jungle Boy, and more. From cosy snug spots to lively DJ parties on weekends, this crawl offers a perfect mix of unique atmospheres, creative cocktails, and great vibes. Whether you're into rum, tiki mugs, or quirky neighbourhood hangouts, this is your ultimate night out in Windsor!
Last updated: July 2025
Dive into Windsor’s lively cocktail scene with this curated crawl through Chapel Street’s most dynamic bars. The journey kicks off at Three Monkeys, where quirky charm meets infectious weekend energy, setting a spirited tone for the night. Next, Better Days energizes the route with playful nostalgia and inventive cocktails, inviting friendly competition over classic games. The momentum builds at Blackwoods, offering an elegant yet unpretentious environment perfect for vibrant conversations and expertly crafted drinks. Holy Grail then shifts the scene into a cozy, ship-themed lounge, blending plush comfort with refined rum and cocktail selections—ideal for gathering with friends or sparking intimate chats. Finally, Jungle Boy transports you to a tropical oasis, where lush greenery and exotic tiki cocktails crown the adventure with bold flavors and a festive atmosphere. Each stop complements the next, ensuring the crawl flows from spirited beginnings to a tropical crescendo, making every sip a step deeper into Windsor’s cocktail culture.
Launching the crawl with infectious energy, Three Monkeys blends quirky charm and weekend DJ beats, setting a lively, upbeat tone that invites connection and celebration right from the start.
The next stop is a quick stroll down Chapel Street, keeping the vibrant energy alive as you head toward Better Days’ playful and welcoming vibe.
Better Days injects fun and nostalgia with its board games and inventive cocktails, providing a spirited yet approachable atmosphere that encourages lively socializing and friendly competition.
The next stop is just a few minutes’ walk further along Chapel Street, guiding you toward Blackwoods’ sophisticated yet energetic scene.
Blackwoods elevates the crawl with an elegant yet unpretentious space, perfect for savoring expertly crafted cocktails amid a buzzing crowd that keeps the night’s momentum soaring.
The next stop is a short, inviting walk down Chapel Street, transitioning you into the cozy, intimate ambiance of Holy Grail.
Holy Grail offers a plush, ship-themed retreat where rich rum selections and handcrafted cocktails bring warmth and depth, creating the perfect setting to unwind and deepen conversations.
The next stop is a lively walk along Chapel Street, energizing you for the crawl’s tropical finale at Jungle Boy.
Jungle Boy closes the night with a splash of tropical flair, lush plants, and exotic tiki cocktails served in iconic mugs—delivering a festive, vibrant atmosphere that leaves the adventure on a high note.
This is the last stop, where you can savor the final bursts of flavor and fun before wrapping up your Windsor cocktail journey.
Ready to turn an ordinary night into a memorable adventure? This Windsor cocktail bar crawl along Chapel Street is your ticket to a dynamic blend of vibrant atmospheres, masterful mixology, and social sparks. Whether you're a cocktail connoisseur or simply crave a night packed with excitement and new connections, this crawl ensures a seamless, exhilarating progression of scents, sips, and scenes. Grab your crew, lace up your walking shoes, and let Windsor’s spirited nightlife sweep you into its lively embrace—one cocktail at a time.
Crawl Map