đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our curated bar crawl featuring five fantastic spots. From the cosy ship-themed Naughty Nancy's with rum & cocktails to the plant-filled Jungle Boy serving tiki mugs, there's something for every cocktail lover. Explore stylish pubs, contemporary lounges, and hidden gems across the town. Perfect for a fun night out with friends, this crawl combines great drinks, lively atmospheres, and plenty of memories in the making!
Last updated: July 2025
Dive headfirst into Windsor’s buzzing nightlife with this expertly crafted cocktail bar crawl along Chapel Street. Kick off the evening at a food-centric pub pulsing with live music and a crowd ready to mingle. From there, shift gears into a playful cocktail den where nostalgic games and inventive drinks spark laughter and new connections. The journey continues through elegant, warmly lit venues where expert mixologists craft cocktails that charm every palate. Cap off the night in a lush, tropical lounge that serves daring tiki concoctions in a vibrant, plant-filled hideaway. This crawl is designed to keep the energy flowing and the good times rolling, perfect for those who crave social adventure and unforgettable sips.
Start strong at this lively, food-forward pub where live music sets the pulse and craft cocktails fuel your night. It’s the energetic launchpad that gets the crowd buzzing and the conversation flowing.
The next stop is just a short, spirited stroll down Chapel Street, keeping the momentum alive with vibrant street energy and anticipation.
Step into a playful scene where retro video games meet inventive cocktails, perfect for sparking camaraderie and shared laughter. This spot adds a lively, interactive twist to the crawl’s journey.
The next stop is a quick, easy walk further along Chapel Street, transitioning smoothly from playful vibes to a more refined cocktail experience.
Elevate the evening at this polished yet approachable venue, where expertly crafted cocktails and a curated wine list invite connection and conversation in an elegant setting.
The next stop is a brief walk, diving back into the heart of Chapel Street’s unique bar scene with a shift toward cozy, themed surroundings.
Immerse yourself in a ship-inspired sanctuary where plush seating and carefully mixed rum cocktails create a warm, inviting space to recharge and reconnect before the final leg.
The next stop is a lively walk that amps up excitement, bringing you closer to the crawl’s tropical finale.
Conclude the night surrounded by lush greenery and bold tiki drinks that deliver a festive, adventurous finish. This vibrant lounge ensures your night ends on a high, spirited note.
The next stop is the end of this thrilling crawl, leaving you perfectly placed to continue your Windsor evening or head home with unforgettable memories.
This Windsor Cocktail Bar Crawl is your ticket to an electrifying night packed with flavor, fun, and fresh social energy. Whether you’re celebrating big or just chasing new experiences, these five stops deliver a seamless flow of unique atmospheres and expertly crafted drinks. So gather your crew, lace up your walking shoes, and let Chapel Street’s cocktail scene ignite your nightlife adventure. Cheers to a night you won’t forget!
Crawl Map