Paul P.
10/25/2025
An excellent spot to stop for drinks on the other end of Duval. Good pours, cold drinks, and you can also buy liquor bottles to go. Live music in the evenings - usually one man guitar singers....
Tipsy Rooster Liquor Store and Bar
$$
Closed
(132)
Photos
1325 Simonton St
Key West, FL 33040
Tipsy Rooster is a local bar and liquor store that features live music and specialty drinks! Its cocktail time all the time in Key West! Have a drink at our bar on your way downtown, meet up with friends to start your Key West adventure or just chill with a specialty drink while relaxing in the sand. We make some of the best specialty cocktails on the island featuring house-infused liquors. We also have a great selection of Beer, Wine, Champagne and all the liquors you need to stock your own bar at home! We feature live music 7 days a week from local artists.
Also at this address
Reviews
4.5132 reviews
Claudia C.
7/13/2025
Absolutely love this place! We've been coming to Tipsy Rooster every year for the past three years, and it never disappoints. The vibe is unbeatable, laid-back, fun, and full of character. Our...
Mark C.
2/24/2025
A hidden gem which isn't really hidden. Right on the street next to Southwinds Hotel and just 2 blocks north of the Southernmost Point. Liquor store bar with a guitarist playing music pretty much...
Andrew M.
9/3/2025
Great place to go in the afternoon before sunset sit back people watch .. great alcohol prices and good food
Marissa R.
9/3/2023
This is a cute little spot, right in the middle of all the "Southernmost" things you could imagine! It was within steps from my hotel, and we had a coupon for a free cocktail from the Santa...
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