đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our Rum & Tiki Bar Crawl! Explore 5 fantastic venues, including Naughty Nancy's, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, Holy Grail, and Jungle Boy. From cozy, ship-themed bars with plush couches to plant-filled lounges serving tropical tiki mugs, there’s something for every cocktail lover. Perfect for a fun night out with friends, this crawl offers a mix of pub vibes, creative drinks, and great atmosphere in the heart of Windsor.
Last updated: July 2025
Kick off your night in Windsor with a cocktail bar crawl that’s anything but ordinary. This curated Chapel Street route pulses with energy, blending bold flavors, inventive mixes, and atmospheres that spark connection and adventure. From the thumping live music and hearty eats at Naughty Nancy’s to the retro gaming and inventive cocktails at Better Days, this crawl builds momentum with every stop. As you weave through cozy, elegant spots like Blackwoods and the ship-themed Holy Grail, anticipation rises toward a finale at Jungle Boy—a tropical hideaway where lush greenery meets daring tiki creations. Get ready for a night where every glass tells a story and every venue flips the script on traditional nightlife.
Launch your crawl amid live music and a vibrant crowd at Naughty Nancy’s, where craft cocktails and hearty bites set an energetic tone that energizes the entire night.
The next stop is a quick, lively stroll down Chapel Street, keeping the buzz alive as you head to a spot that blends nostalgia with fresh cocktail creativity.
Step into Better Days to ignite your playful side with inventive cocktails and vintage video games, offering a unique mix of fun and flavor to elevate the vibe.
The next stop is just a brief, inviting walk that transitions you into a sleek and stylish setting perfect for intimate conversations and refined drinks.
Blackwoods delivers a polished yet approachable atmosphere, where expertly crafted cocktails and a curated wine selection provide a sophisticated pulse to the crawl.
The next stop is a short walk that shifts the scene into a cozy, themed venue where nostalgia and fine spirits meet for a memorable experience.
At Holy Grail, the ship-inspired décor and attentive cocktail crafting invite lively chats and group celebrations, balancing the night’s energy before the grand finale.
The next stop is a brief stroll that carries you into a vibrant, tropical oasis, ramping up excitement with exotic drinks and lush surroundings.
Conclude your adventure at Jungle Boy, where tiki mugs, tropical greenery, and daring cocktails spark a festive climax to your Windsor cocktail quest.
This final stop wraps up the crawl in style, with no more walking needed—just time to savor the island-inspired buzz and celebrate the night’s journey.
Whether you’re chasing bold flavors, live music, or playful nostalgia, this Windsor cocktail crawl delivers nonstop excitement from start to finish. So gather your crew, pace your pours, and dive into a night where every sip and step brings fresh surprises. Ready to own the night? Windsor’s cocktail scene is waiting to thrill.
Crawl Map