The battle over Hemingway's favorite watering hole ends here. Captain Tony's Saloon was the original location of Sloppy Joe's (and its previous incarnation as a speakeasy) where the famed author haunted a bar stool until 1938. History lesson aside, today it's the definition of a dive bar--license plates on the walls, bras and undergarments strewn on the ceiling. The bar stools have patron's names on them (literally), and the place is lacking of any natural light. The "hanging tree" where 19 pirates met their fate grows through the floorboards and out the ceiling. Like a handful of other Key West pubs, not much has changed here since Hemingway ordered his first scotch and soda.
This all-welcome, gay night club has creative events every day of the week from afternoon to evening. Stop in for no-limit Texas Hold'em poker tournaments, Aqua's American Idol karaoke with proceeds that go to charity and dueling bartenders who sing as they shake and stir their cocktails. Their nightly drag shows, featuring the Aquanettes, get rave reviews from locals and tourists alike for the caliber of the performances and the hilarity that ensues.
Opened in late 2012, the Little Room Jazz Club is a refreshing change in the hectic (and similar) Duval Street music scene. Find a new favorite glass of wine from the extensive listing, as you listen to live jazz, blues and even Cuban-fusion bands.
|Rick's (Durty Harry's)|
With eight bars built in to this complex, you can easily party all night at Rick's Key West. The Duval Street institution offers late night karaoke (until 4:00 a.m.), the Durtbags cover band, and several DJs that turn up the bass into the wee hours of the morning. The live music roster is sure to have patrons on their feet with rock-and-roll covers of bands like Blink 182, Godsmack, AC/DC and others.
Located on Duval just next to the Tropical Inn, Vinos on Duval it's 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.
Nestled between Key West Harbor and Mallory Square, Sunset Pier is all about location, location, location. Of course the live music, vivid decor, Caribbean fare and lip-smacking libations don't hurt either. Each night thousands of visitors flock to Mallory Square for the famed sunset celebration, and while Sunset Pier is in the heart of the action, it offers a bit of a buffer between you and the crowds. The menu is a mix of Key West seafood classics like conch fritters, crab cakes and raw bar favorites paired with Cuban cuisine.
Tucked behind La Trattoria restaurant, Virgilio's (named after the founder of the restaurant) is an elegant indoor/outdoor cocktail bar popular with the swanky over 30 crowd. Perfectly mixed martinis are the house specialty in yummy flavors like mint chocolate chip and Key lime pie. If you have trouble choosing from their extensive selection, the bartenders can help you find the right drink to fit your mood. Kick back either on the outside patio covered with a tree canopy or at the second bar under the roof. Nightly, people hit the dance floor for live music, usually jazz, blues or Latin. If you're feeling peckish, you can also nosh on items from a limited menu by the restaurant.
Steps from the controlled chaos on Duval Street, The Porch is a craft beer lover’s refuge tucked into the front of a 1839 Victorian mansion. They have 18 brews on tap and plenty more in bottles with selections changing with the seasons. Wine aficionados will also be pleased with their full wall of wine, interrupted only by a flat screen TV playing B-movies (ironically of course). The décor mixes historic architectural details like pressed tin ceilings and chandeliers with 80s music, a Buddha statue and an R2D2 in a Santa hat. It's been likened to "Cheers" on acid.
|The Green Parrot|
Filled with mix of local characters and visitors-in-the-know, "The Parrot," is not your typical dive bar. As the oldest watering hole in Key West, they've got nothing to prove, and their motto, "No Sniveling," illustrates their no-nonsense approach to slinging stiff drinks. Tropical breezes and ceiling fans keep the open-air bar cool, and the old-school jukebox mixes B.B. King with The Temptations and New Orleans Funk. They only have popcorn to munch on, but there is a BBQ joint next doorif you get hungry.,
|The Rum Bar at the Speakeasy Inn.|
Stop by and visit with "Bahama Bob" at the Rum Bar at the Speakeasy Inn. The friendly mixologist is well-versed in the art of bartending and world of rum. While the staff at the fraternity-style pubs on Duval Street toss together a Jack and Coke, Bahama Bob will make you a Pain Killer from scratch (with fresh ground nutmeg), and mojitos muddled with mint and lime juice (no mixers here). If you are new to rum, a sampler lets you ease your way in, and the bartenders are happy to answer any questions you may have.