đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our curated bar crawl! Visit five fantastic venues including Naughty Nancy's, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, Holy Grail, and Jungle Boy. From cosy ship-themed pubs with plush couches to plant-filled tiki lounges, this crawl offers a mix of rum, cocktails, and great vibes. Perfect for a night out with friends who love good drinks, cool atmospheres, and a little adventure. Let’s make your night unforgettable!
Last updated: July 2025
Fuel your night with a dynamic cocktail bar crawl through Windsor’s Chapel Street, where every stop amps up the energy and social buzz. Kick off at Naughty Nancy’s, where live bands and craft cocktails set an electric tone. Next, shift gears into playful mode at Better Days Cocktail Bar, blending inventive drinks with nostalgic games that spark laughter and connection. The journey then deepens at Blackwoods Wine & Cocktail Bar, balancing sophistication with a welcoming atmosphere that suits any kind of gathering. As the night unfolds, Holy Grail invites you to a ship-inspired setting with smooth rums and handcrafted cocktails crafted right before your eyes — perfect for intimate chats or group cheers. Finally, wrap up your adventure at Jungle Boy, a lush tropical retreat where exotic tiki cocktails and vibrant décor create an unforgettable finale. This carefully curated crawl flows seamlessly from upbeat energy to intimate charm, guaranteeing a night packed with flavor, fun, and social adventure.
Launch your crawl amid the buzzing energy of Naughty Nancy’s, where live music and inventive cocktails create a spirited atmosphere that fires up the night’s excitement.
The next stop is a short, lively stroll down Chapel Street, keeping the momentum flowing as you head to Better Days Cocktail Bar.
Step into a playful world of retro games and creative cocktails at Better Days, where the upbeat vibe invites camaraderie and sparks lively conversations.
The next stop is a quick walk along Chapel Street, maintaining the vibrant energy en route to Blackwoods Wine & Cocktail Bar.
Elevate your evening at Blackwoods, where expertly crafted cocktails meet a sophisticated yet inviting setting, perfect for connecting over fine drinks.
The next stop is a brief, engaging stroll down Chapel Street, leading you toward the unique atmosphere of Holy Grail.
Immerse yourself in the ship-themed charm of Holy Grail, where rum-focused cocktails and cozy booths encourage easy conversations and shared moments.
The next stop is a lively walk along Chapel Street that sets the stage for the tropical escape waiting at Jungle Boy.
Conclude your adventure in a vibrant jungle of greenery and tiki mugs, where tropical cocktails and a spirited vibe deliver a memorable finale.
This is the final stop on the crawl, best savored without a walk afterward to hold onto the night’s electric energy.
Ready to own the night? This Windsor cocktail bar crawl promises an exhilarating ride through Chapel Street’s best spots, each offering a fresh twist on social drinking and vibrant atmospheres. Gather your crew, pace your sips, and dive into the rhythm of the city’s most exciting cocktail journey. Share your stories, snap your moments, and raise your glass to a night of unforgettable fun and spirited adventure!
Crawl Map