đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s best cocktail bars on this fun-filled crawl! Explore five fantastic venues including Naughty Nancy's with its ship-themed decor, Better Days with tropical tiki mugs, Blackwoods Wine & Cocktail Bar, Holy Grail, and Jungle Boy’s lush lounge. Whether you're into rum, tiki, or classic cocktails, this pub crawl offers a mix of cosy atmospheres, stylish bars, and unforgettable drinks. Perfect for a night out with friends—drink, laugh, and make memories!
Last updated: July 2025
Embark on a thrilling night out in Windsor with this expertly curated cocktail bar crawl along the iconic Chapel Street. Each stop amps up the excitement with distinct personalities—from the pulsating energy of live music to nostalgic game nights, and from polished wine bars to thematic lounges that transport you to tropical escapes. This crawl is designed for adventurers who crave dynamic vibes, bold flavors, and unforgettable social moments. Get ready to sip, mingle, and explore a lineup of venues that fuel the night with infectious energy and crafted creativity.
Kick off your crawl with Naughty Nancy’s, where lively live music and craft cocktails set a high-energy tone. Its food-centric approach fuels the night, making it the perfect launchpad for an adventure filled with flavor and fun.
The next stop is a brief and spirited stroll along Chapel Street to Better Days Cocktail Bar, keeping the momentum alive with its inviting game-filled lounge.
Step into Better Days to unleash your playful side with inventive cocktails and a lively collection of board and video games — a perfect social hub that blends nostalgia with fresh, creative drinks.
The next stop is a short, energetic walk down Chapel Street to Blackwoods Wine & Cocktail Bar, shifting the vibe toward refined craft and elegant ambiance.
Blackwoods brings sophistication and warmth to the crawl, offering expertly crafted cocktails and a curated wine list that invite deeper connections in a stylish yet approachable setting.
The next stop is an easy, mood-setting walk to Holy Grail, where the scene transforms into a charming, ship-inspired retreat.
At Holy Grail, sink into plush booths and antique chairs as you savor rum-forward cocktails in a cozy, nautical atmosphere that encourages lively conversation and a sense of discovery.
The next stop is a quick, vibrant stroll to Jungle Boy, raising the energy with tropical vibes and exotic cocktail creations.
Conclude your crawl amid lush greenery and bold tiki cocktails at Jungle Boy, where the adventurous spirit shines through unique drinks served in iconic mugs—an unforgettable finale to an electrifying night.
The next stop is the end of the crawl, leaving you perfectly poised to continue your Windsor night or savor your last cocktail moment here.
From the first clink of a glass at Naughty Nancy’s to the final tropical sip at Jungle Boy, this Windsor cocktail bar crawl delivers an exhilarating night packed with bold flavors, vibrant atmospheres, and social sparks. Whether you’re a seasoned cocktail explorer or looking to ignite your night out, this curated route along Chapel Street promises an unforgettable journey. Grab your crew, pace yourself, and let the spirit of Windsor’s best cocktail bars carry you through an adventure of taste and atmosphere you won’t forget.
Crawl Map