NightLife
Sloppy Joe’s
No place is quite as synonymous with the Key West spirit as Sloppy Joe’s, which has been around since December 5, 1933 - the day Prohibition was repealed. Hemingway and his “Mob” of cohorts were enthusiastic regular customers. In fact, the author once called himself a co-owner of the enterprise. The “Mob” was comprised of some of the literary lights of the time, as well as a variety of famous and infamous local residents. Over the years, Sloppy Joe’s has gained a richness and flavor while essentially remaining unchanged. The bar offers generous drinks, live music and dancing, and the menu includes American Caribbean fare with bar favorites such as burgers, sandwiches and salads. In mid-July each year, Sloppy Joe’s is thronged with cheerful bearded men competing for the title of Hemingway Look-Alike.
Rick’s
Rick's is Key West's largest and most famous entertainment complex, featuring eight unique bars in one venue. It has the perfect combination of everything Key West - dance clubs, VIP bars, adult entertainment, premium drink bars, balcony bars sporting incredible views of Duval, and live rock n’ roll entertainment.
The Bull/Whistle Bar/Garden of Eden
The Bull and Whistle are two bars in one. Large crowds gather around the central bar to watch live music on the Bull’s intimate performance stage, while the Whistle plays host to sport lovers. Shoot a game of pool, play darts, or people watch while sitting on one of the many stools that line its famous balcony. Venture to the third floor where you will find the Garden of Eden - Key West’s only clothing-optional bar.
Willie T’s
Live music fills the air daily at Willie T’s. Popular for its outdoor setting on Duval Street, this bar is well known for its famous mojitos. The ceilings and walls are adorned with dollar bills from patrons past. Stop on through for a beverage and some live tunes - they serve up happy hour daily from 4PM-7PM.
Fat Tuesday
Straight from Bourbon Street in New Orleans and dropped in the middle of Duval Street comes Fat Tuesday Key West. Dance to their nightly house DJ as you party like it's Mardi Gras. Fat Tuesday offers endless frozen drink options - try a Blood Orange Margarita, a Strawberry Margarita, or make your own creation! Fat Tuesday always promises a good time, especially since their famous frozen daiquiris are some of the strongest on the island.
Hog’s Breath Saloon
As one of Key West’s favorite and iconic hotspots, Hog’s Breath Saloon has entertained Key West locals and guests for almost 35 years. With daily live entertainment that features the best in local as well as nationally-acclaimed bands, Hog’s Breath Saloon is the ideal nook to get off hot Duval and enjoy food, good times, and drinks. Remember - Hogs Breath is Better Than No Breath at All!
The Green Parrot
The Green Parrot is a true Key West icon and the ideal place to let loose with friends. Every night, the great music, original beverages, and groups of Conch locals combine with Key West visitors to make for a place of misadventures, excitement, and pure fun. From hurricane parties to divorce celebrations and pet birthdays, the true Key West spirit of the Green Parrot never changes and welcomes everyone with open arms. This landmark bar is less than two blocks from Island Breezes.
IRISH KEVIN’S
Irish Kevin’s offers a full bar with unique cocktails and twenty-six beers on tap. Live entertainment is served up seven days a week from early in the morning until closing time. All are welcome to sing-along and even become part of the show. Plenty of televisions ensure you won’t miss out on your favorite sporting events. Be sure to come hungry as they have a tasty food menu ranging from a light salad to a one pound burger.
Captain Tony’s Saloon
The original Sloppy Joe’s Bar, this historical saloon has been loved for decades by locals and visitors alike, as well as iconic figures like Tennessee Williams, Truman Capote, and, of course, Ernest Hemingway. Captain Tony was an avid fisherman, rumrunner, casino manager, and even the mayor of Key West, who built the saloon with the intention of offering ice cold drinks to his fellow Key Westers - a tradition that everyone still loves to participate in. Above the sign outside the building is a large Jewfish that Captain Tony caught and had preserved. It is said that if you throw a quarter into the mouth of the fish, good luck will follow you until you leave the island.
VINOS ON DUVAL
Located on Duval just next to the Tropical Inn, Vinos on Duval is a refreshing change of pace. The intimate environment invites conversation, and sharing a bottle and cheese plate is the way to go. They have an extensive selection of reds, whites and sparkling wine, and the list is constantly changing to keep things fresh and exciting. Not a wine connoisseur? No problem. This is a great place to find a new wine that you love, and the bartenders will guide you in the right direction. They also offer a sampling of gourmet sandwiches and desserts from Croissants de France.
WINE-O
Experience an inviting wine bar nuzzled in the energy of Duval Street. Wine-O features a variety of wines from around the world. Surround yourself in an upscale atmosphere with fine wine and good people. Enjoy a bottle in their sleek, sophisticated lounge, or take a few bottles to go. Enhance your wine experience with one of their chef-prepared cheese and charcuterie boards. Their extensive collection of wines includes your favorites, cult-classics, and hard-to-find gems from top wineries around the country.
801 Bourbon Bar
There’s always fun at the 801! For over 25 years, 801 Bourbon has been home of Sushi and her 801 Girls. You may have seen the drag diva on CNN being ceremoniously lowered in a six-foot red high heel as a countdown to the New Year in Key West. This multi-story complex features world famous drag shows every night at 9PM and 11PM. Each Sunday, participate in Not Your Mama’s Bingo and enjoy karaoke 4PM - 9PM.
La Te Da Cabaret and Piano Bar
La Te Da Hotel is renowned for its first class entertainment - the Cabaret features original shows from top performers such as Christopher Peterson and Randy Roberts, known for their lively and humorous Broadway style shows in Key West. Both performers offer impersonations of iconic showbiz greats such as Cher, Judy Garland, Better Midler and many, many more. There are lots of drag shows in Key West, but La Te Da Cabaret offers so much more as their entertainers sing live and produce their own unique performances, which have wowed audiences both in Key West and countrywide for many years. It is recommended that you book in advance and arrive early to ensure you get a good seat. Order one of their fabulous cocktails, sit back, and enjoy the show!
Aqua Nightclub
“Reality is a drag!” Are you looking for the best music, lights, sounds and DJs in town? Aqua Nightclub is the premier gay nightspot in Key West. The friendly staff follows Key West’s motto - One Human Family - welcoming all through their doors. The club is home to the Aquanettes, who perform drag shows nightly. Happy hour is daily from 3PM to 8PM.
