đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our fun-filled crawl through 5 top venues! Sip on rum and creative cocktails in a cosy, ship-themed bar, enjoy tiki mugs in a trendy plant-filled lounge, or relax in plush couches at stylish spots. Perfect for food lovers and nightlife enthusiasts, this crawl takes you from Naughty Nancy's to Jungle Boy, offering a mix of pub charm, contemporary vibes, and unforgettable drinks. Grab your friends and toast to a night of great drinks and good times!
Last updated: July 2025
Dive headfirst into Windsor’s buzzing cocktail culture with this exhilarating Chapel Street crawl. Kick off your night at Naughty Nancy’s, where live music and bold flavors set an energetic stage. From there, shift gears at Better Days, a playful spot blending nostalgic games with creative cocktails that spark laughter and connection. Blackwoods invites you next to indulge in refined sips and a welcoming ambiance, perfect for lifting the night’s tempo. Cruise on to Holy Grail’s ship-inspired hideaway, where classic rums and handcrafted cocktails invite intimate chats amid plush seating. Finally, cap off the adventure at Jungle Boy, a tropical oasis boasting vibrant tiki vibes and daring concoctions that keep the energy soaring. Each stop unfolds a new layer of excitement, making this crawl a dynamic journey through Windsor’s spirited nightlife.
Naughty Nancy’s blasts open the crawl with its lively pub atmosphere, live music energy, and food-forward cocktails that fuel the night ahead.
The next stop is a quick stroll along Chapel Street, keeping the buzz alive as you head to a cozy cocktail haven.
Better Days amps up the social vibe with playful board games, retro video fun, and inventive cocktails, perfect for sparking connections and keeping energy high.
The next stop is a short walk that carries you deeper into Chapel Street’s cocktail scene, transitioning into a refined yet vibrant setting.
Blackwoods elevates the crawl with expertly crafted cocktails and a polished yet approachable atmosphere, perfect for savoring quality drinks and engaging conversations.
The next stop is just a few minutes’ walk, shifting the mood toward a more intimate and thematic experience.
Holy Grail delivers a unique ship-themed escape where rich rums and mixology mastery meet cozy nooks, adding depth and character to the evening.
The next stop is a brief walk that leads you to a vibrant tropical lounge to finish the crawl on a high note.
Jungle Boy wraps up the crawl with its lush tropical decor, bold tiki cocktails, and inviting energy that keeps the night alive and adventurous until the last sip.
This final stop crowns the crawl; no walk needed as you settle into Jungle Boy’s lively oasis to celebrate the night’s adventures.
Ready to explore Windsor’s cocktail gems? This crawl delivers a dynamic journey through bold flavors, playful vibes, and spirited social scenes that will have you craving more. Whether you’re out with friends or meeting new ones, let each stop ignite your night with fresh energy and unforgettable drinks. Gather your crew, map your route, and dive into Windsor’s most exciting cocktail adventure yet.
Crawl Map