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. When the landlord was set to raise the rent $1, owner Captain Joe Russell ("Sloppy Joe") and his customers moved the entire bar to its current location on Duval Street. 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.
Recommended for Bars because: Soak up some history at this dimly-lit dive bar, once the home of the original Sloppy Joe's and speakeasy where Hemingway held court.
Claudia's expert tip: Ask for the Pirate's Punch--it's their signature cocktail.
This funky Duval Street bar is a must-do on any Key West itinerary. Female impersonators take the stage at the cabaret, including the legendary Sushi, who has been making a name for herself on the island for more than 25 years. Expect singing, dancing, a bit of raunchy comedy and audience participation. There are two cabaret showings at 9:00 p.m. and again at 11:00 p.m. nightly. (Note: the late-night show is known to be more R-rated than the early show.) Make sure to bring lots of small bills, as tipping the performers is highly encouraged. Check at your hotel for a coupon for a discount on the cabaret cover charge. On Sundays, drag queen bingo with QMitch is a fave for locals and visitors alike, so get there early to snag a seat. Beware: some of the prizes are rather risque.
Recommended for Bars because: This funky, Duval Street bar is a must-do on any Key West itinerary with its drag queen cabaret, bingo and karaoke.
Claudia's expert tip: Want to meet some of the drag queens before the show? They usually greet passersby on Duval Street in front of the bar and are happy to pose for photos.
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. The performers get the audience involved, so if you don't like to be in the limelight, choose a seat away from the walkways. After the shows, the bar becomes an all-out dance party that is not to be missed.
Recommended for Bars because: This all-welcome, gay night club features over-the-top drag performances and non-stop dancing til the wee hours.
Claudia's expert tip: The performers get the audience involved which makes it even more fun! If you don't like to be in the limelight, choose a seat away from the walkways.
The Little Room Jazz Club & Wine Bar is a refreshing change amidst the Duval Street Troprock scene. Find a new favorite glass of wine from the extensive listing, as you listen to live jazz, blues and even Cuban-fusion bands. A 70-inch television has a feed from the Atlantis aquarium, and all the furnishings have an elegant, polished look. Both indoor and outdoor seating are available, and the music starts early every day. Happy Hour includes 2-for-1 specials on hand-crafted specialty cocktails.
Recommended for Bars because: For a change of pace, mellow out at the snazzy Little Room Jazz Club with a glass of wine and top-notch live music.
Claudia's expert tip: The music starts early every day, so get there ahead of time for the best seat.
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. The Durtbags alone are worth coming out to see; they rock the stage. At Rick's Upstairs, the DJs spin the best beats seven nights a week, while patrons shimmy on the multi-level dance floor under the mirrored disco ball.
Recommended for Bars because: The younger crowd (or young at heart) can boogie to DJ beats at Rick's Upstairs or rock with the Durtbags at the Tree Bar.
Claudia's expert tip: Durty Harry's offers military discounts and drink specials during big sporting events.
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. They also offer a sampling of gourmet sandwiches and desserts from Croissants de France. The comfy porch on Duval Street allows you to slowly watch the world go by as you sip on a fine wine. Don't miss their $5 sangria happy hour, and check their calender for other wine tastings and special events.
Recommended for Bars because: This cozy wine bar is a locals fave, serving up an ever-changing selection of top wines paired with delicious cheeses.
Claudia's expert tip: They deliver! From 2:00 p.m. to 1:00 a.m. they offer free delivery on bottles of wine to your hotel. You must provide ID upon delivery.
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. The cocktail menu overflows with six twists on the margarita and four caipirinha flavors along with other vacation mainstays like frozen drinks topped with an extra shot of Cruzan dark rum. Go full-on tourist and order the Liquid Jelly Monkey Luv rum punch, served in a Sunset Pier logo carved coconut. Settle in for the best light show in town.
Recommended for Bars because: Plop down onto one of the brightly colored stools for the best sunset view in town paired with live music, Caribbean fare and lip-smacking libations.
Claudia's expert tip: Not into crowds? Head to Sunset Pier for lunch.
Steps from the controlled chaos on Duval Street, The Porch is a craft beer lovers 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. Sit at the small bar where friendly bartenders like "Grubby" will guide you through their selections, or on the namesake porch--a perfect perch for people watching. Happy Hour is ideal for anyone who wants to try a new brew or wine without breaking the bank. Watch their schedule for theme parties.
Recommended for Bars because: Hidden just steps from Duval Street, The Porch is a craft beer lovers refuge tucked into an emerald 1839 Victorian mansion. "Cheers" on acid, anyone?
Claudia's expert tip: They don't serve food, but they'll happily provide you with delivery menus from local restaurants.
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 Snivelling," 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. At night, bands from around the country up the ante with a heady mix of gritty blues, rock and funk. Just to keep things interesting, the Green Parrot Ukulele Association plays once a month. If you're not a late-night person, at 5:30 p.m. the bands do an early sound check set.
Recommended for Bars because: "The Parrot" is best dive bar to enjoy colorful characters, strong drinks and the best live music in town. Remember, "No Snivelling."
Claudia's expert tip: Check their website for updates and events schedule.
Stop by and visit with the friendly mixologists at the Rum Bar at the Speakeasy Inn (an actual former speakeasy from the Prohibition days). While the staff at the fraternity-style pubs on Duval Street toss together a Jack and Coke, these bartenders will make you a Pain Killer from scratch (with fresh 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 intimate space makes it easy to make friends and settle in for a while.
Recommended for Bars because: A visit with these mixologists and rum experts is a must for a handcrafted cocktail and rum education.
Claudia's expert tip: After you've had a few, ask for a shot of their potent "Root Juice."