đź“… Open Today: Crawl likely open on Fridays
Join us on a lively Windsor cocktail bar crawl through five fantastic venues! Explore cozy, ship-themed bars like Three Monkeys, sample vibrant tiki mugs at Jungle Boy, and enjoy plush couches and antique chairs at Blackwoods. From quirky neighbourhood hangouts with DJ parties on weekends to stylish, plant-filled lounges, this crawl offers a perfect mix of atmosphere, great drinks, and good vibes. Whether you're into rum, cocktails, or just a fun night out, this is your ultimate Windsor experience.
Last updated: July 2025
Kick off your evening adventure in Windsor with an exhilarating cocktail bar crawl that pulses with energy and crafted creativity. This route through Chapel Street’s finest bars captures the essence of vibrant nightlife — from quirky charm and nostalgic gaming to tropical escapes and ship-themed sophistication. Each stop amps up the excitement, encouraging connection, discovery, and spirited fun. Whether you’re rallying friends or meeting new faces, this crawl’s electric mix of inventive drinks and dynamic atmospheres guarantees a night brimming with social thrills and memorable moments.
Start your night at Three Monkeys, where quirky character meets pulsing weekend DJs. Its intimate yet energetic vibe sets the tone for lively conversations and expertly crafted cocktails, launching your crawl with infectious enthusiasm.
The next stop is a brief stroll down Chapel Street, keeping the energy high as you head toward a playful, interactive setting.
Better Days invites you into a lively, nostalgia-infused space where inventive cocktails meet board games and retro gaming projections. This stop ups the social playfulness, sparking laughter and friendly competition.
The next stop is just a short, engaging walk along Chapel Street, guiding you toward a refined yet approachable cocktail and wine haven.
Blackwoods elevates the night with its seamless blend of craft cocktails and curated wines. Its sophisticated warmth provides a stylish backdrop perfect for deepening conversations and savoring impeccable drinks.
The next stop is a quick, inviting walk that shifts the vibe to cozy, ship-inspired charm with plush seating and curated rum selections.
Step aboard Holy Grail’s ship-themed sanctuary for a refined yet lively atmosphere. Plush booths and antique details create a unique setting where rum and cocktails take center stage, perfect for groups ready to dive deeper into the night.
The next stop is a short, atmospheric walk that transitions you into a tropical lounge bursting with greenery and vibrant cocktail artistry.
Conclude your crawl at Jungle Boy, a contemporary tropical oasis where tiki mugs and lush plants amplify the electric energy. Its inventive cocktails and spirited ambiance make for an unforgettable finale that leaves you craving the next adventure.
This is the final stop, perfectly positioned to cap off your vibrant night on Chapel Street.
This Windsor cocktail crawl offers a thrilling journey through Chapel Street’s most dynamic bars, each stop unveiling new flavors, scenes, and social sparks. Whether you’re chasing innovative mixes, nostalgic fun, or lively atmospheres, this crawl delivers an unbeatable night of connection and celebration. Lace up your walking shoes, rally your crew, and set out to conquer Windsor’s cocktail hotspots—adventure awaits with every sip.
Crawl Map