đź“… Open Today: Crawl likely open on Fridays
Ready for a night of sips and socialising? Explore Windsor's vibrant cocktail scene with our curated crawl featuring five fantastic venues. From Naughty Nancy's cozy ship-themed bar with plush couches to Better Days' tiki mug cocktails in a plant-filled lounge, this crawl has it all. Whether you're into classic pub vibes at Blackwoods, the legendary Holy Grail, or the jungle-inspired Jungle Boy, you'll enjoy a mix of food-centric spots, lively pubs, and stylish bars. Perfect for a fun night out with friends!
Last updated: July 2025
Dive headfirst into Windsor’s energetic cocktail scene with this adventurous Chapel Street bar crawl. From the moment you step into Naughty Nancy’s bustling pub atmosphere, the night unfolds with a dynamic pulse—live music, flavorful food, and craft cocktails set the tone. Transition seamlessly into Better Days Cocktail Bar, where playful nostalgia and innovative drinks spark laughter and connection. Blackwoods Wine & Cocktail Bar ups the ante with sophisticated mixes and a welcoming crowd, priming you for the cozy yet spirited ambiance of Holy Grail’s ship-themed interiors. Finish strong at Jungle Boy, a tropical oasis where exotic tiki cocktails and lush greenery invite you to toast the night away. This crawl crafts a natural flow of energy and vibe shifts, ensuring every stop delivers fresh excitement and social adventure.
Kick off the crawl with Naughty Nancy’s vibrant pub energy—where live music, hearty bites, and inventive cocktails fuel the night’s excitement and set a dynamic social stage.
The next stop is just a short stroll along lively Chapel Street, keeping the buzz alive as you head to Better Days Cocktail Bar.
Step into a playful retreat at Better Days, where nostalgic games and expertly crafted cocktails create an upbeat, fun-loving atmosphere perfect for sparking conversations and shared smiles.
The next stop is a brisk walk down Chapel Street, building anticipation for the elevated vibes awaiting at Blackwoods Wine & Cocktail Bar.
Elevate your evening at Blackwoods, where refined cocktails and a curated wine list meet a lively yet polished setting—perfect for connecting over quality drinks as the night deepens.
The next stop is just a few minutes’ stroll, shifting the mood toward an inviting, themed experience at Holy Grail.
Enter Holy Grail’s ship-inspired sanctuary, where plush seating and skillfully crafted rum cocktails ease the vibe into a cozy yet spirited zone, ideal for lively chats and group camaraderie.
The next stop is a short, energetic walk continuing down Chapel Street, leading to the tropical charm of Jungle Boy.
Cap off the crawl at Jungle Boy’s tropical lounge, where exotic tiki drinks and lush greenery create a vibrant finale to your night—inviting you to celebrate with bold flavors and island-inspired fun.
The crawl concludes here, leaving you in the heart of Windsor’s lively nightlife scene.
This Windsor cocktail bar crawl is your ticket to an unforgettable night packed with diverse flavors, lively atmospheres, and endless social energy. Whether you’re a cocktail connoisseur or just chasing a thrilling evening out, these Chapel Street gems deliver a seamless journey through innovation, charm, and spirited fun. Gather your crew, pace yourself, and let the adventure unfold sip by sip.
Crawl Map