Tipsy Rooster Liquor Store and Bar

Experience a Premier Key West Liquor Store with Exceptional Live Music

Tipsy Rooster is a premier Key West liquor store and bar located in Old Town Key West at 1325 Simonton Street. Visitors are welcomed into a vibrant venue offering a unique fusion of premium locally distilled spirits and specialty cocktails crafted with house-infused liquors—perfect for a sunset sip or a spirited rum run.

The establishment bursts with energy as local musicians enliven the atmosphere with live music every weeknight from 8 PM to 11 PM and on Fridays and Saturdays from 1 PM to 4 PM. For those seeking a customized celebration, tailored private events are available with personalized drinks, music, and ambiance, ensuring each event is truly unforgettable. Strategically situated just two blocks from the iconic Southernmost Point, Tipsy Rooster provides ample parking and boasts extended operating hours: Sunday–Thursday (10 AM–1 AM) and Friday–Saturday (10 AM–2 AM). This dynamic venue is the ideal destination for those looking to elevate their Key West adventure with an immersive mix of flavors and entertainment.