You'd be hard-pressed to hear about Key West without hearing about the infamous Sloppy Joes bar, where people come to get – well – sloppy. It was one of Hemingway's favorite watering holes ("Sloppy Joe" was Captain Joe Russell, the founder and one of Hemingway's drinking buddies), and remains a popular place for pub grab and live music. which starts at noon daily and lasts until 2a.m. Attached to the main bar is Joe's Tap room, with several craft beers on tap. By nightfall, this place starts to get rowdy and the tables are cleared away to make room for dancing.
Recommended for Live Music because: If you happen to pass by Sloppy Joe's and don't hear live music, it's because the band is on a beer break.
Local Expert tip: To beat the heat, try a refreshing Papa Dobles, Hemingway's fave cocktail, made with Bacardi, Maraschino Liqueur, lime and grapefruit juices.
Behind La Trattoria, Virgilio's – named after the founder of the restaurant – is an elegant spot for a cocktail. Single malt scotch, fine wines Perfectly mixed martinis are the house specialty - which are just $5 on Mondays. Every night there is live music, usually jazz or blues, and tends to attract the over 30 crowd. Even if cocktail lounges are not your thing a visit to Virgilio's is worth it just to see the ornate tables. They are inlaid, mosaic-style, with colorful tiles and every table is different, and offers a change from the Duval Street music scene.
Recommended for Live Music because: Virgilio's makes for a well-rounded evening of dinner and entertainment.
Local Expert tip: Thursdays are Latin dance night!
Launched in 2006 by former Philadelphia 76ers President Pat Croce, the Rum Barrel offers a happening place to watch the game (particularly when Philly is playing) with plenty of spirits and great food to boot.There are over 150 rums and an extensive collection of specialty and craft beers, plus live music on the Quarterdeck stage like Caribbean and house bands as well as more well-known singers like Bo Bice (American Idol). The menu consists of killer burgers, and seafood items like fish tacos, and lobster pot pie that aren't your typical pub grub. Happy Hour kicks off from 4 to 7pm during football season.
Recommended for Live Music because: Musicians from all over the world take the stage at the outdoor bar.
Local Expert tip: For in-depth information about rum, download their Rum Bible before visiting.
Originally founded in Fort Walton Beach in the mid-70's, the Hog's Breath in Key West has been in business for almost 20 years. The bar motto is "Hog's breath is better than no breath at all" and this philosophy has been embraced by the regulars who come here to drink with wild abandon. In the fall, the bar hosts an annual "Hair of the Hog" home-made bikini contest that kicks off with Bloody Mary's first thing in the morning. Live music is often on the menu up to three times a day (starting as early as 1pm) and a raw bar provides snacks. If you can't make it out, tune in on one of the new webcams!
Recommended for Live Music because: This is a classic Key West dive bar: sticky tables, sticky floors, and great music!
Local Expert tip: Try the Key Lime shooters!
While many parts of Key West have seen modern changes, Schooner Wharf maintains that "old Key West" atmosphere - from the salvage wreckage decor, to the interesting characters that linger around the waterfront. It is also the home of the largest fleet of working schooners on the East Coast, and for two years the bar was actually located on the Schooner Diamante before moving to its current location. When the sun goes down live music and magic tricks take over. With two (and sometimes three) Happy Hours, it's hard to pay full price in this bar. If you have never had a dark and stormy, try one!
Recommended for Live Music because: Live music is that much better when you're listening it on the waterfront!
Local Expert tip: Be sure to check their special events listing.
A true cowboy bar, the newly re-opened Cowboy Bill's Honky Tonk Saloon features line dancing, live country music performers, and - of course - a mechanical bull for watching wannabe cowboys try and show off. On select nights, they offer sexy bull riding contests (with ladies in bikinis), karaoke and ladies night. Be sure to check out the new back bar, cleverly called "the library." On game days, you can catch all the action on 20 TVs including 15 huge projection screens. Salsa Loca, their in-house restaurant, serves fresh Mexican food to pair with frosty buckets of Bud Light beer. They offer plenty of drinks specials and Happy Hour discounts from 3 p.m. - 6 p.m., including half-off well drinks, domestic beer, and appetizers. Their signature drink, the Cruzan Confusion (pineapple, rum, coconut) is amazing!
Recommended for Live Music because: This is the spot to be in Key West for country music lovers!
Claudia's expert tip: Visit their Facebook page to stay updated on special events.
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. While they only have popcorn to munch on, the BBQ joint next door, Charlie Mac's, will send over a waiter and bring you a to-go order. 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 Live Music because: It's the kind of place that draws a crowd of listeners both outside and in.
Local Expert tip: Check their website for updates and events schedule.
Many of Duval Street's pubs are hole-in-the walls devoid of any natural light, but the Tuna is tucked away on Charles Street, leaving plenty of room for a sprawling outdoor area with a large performance stage and several outdoor tiki-style bars. Live music kicks off every night, with two shows on the weekends (check their online schedule). The restaurant and raw bar remains open until 10pm, but the fun continues after the kitchen closes. The menu has all your Key West favorites: conch fritters, peel and eat shrimp, fish sandwiches, burgers, a raw bar, and of course, tuna melts and smoked tuna dip. Grab a seat at the bar or find a spot in the shade under the giant tree, order yourself a bottle of their Smokin' Tuna Ale (or one of their killer margaritas), and enjoy the show.
Recommended for Live Music because: This newcomer on the block has been delivering some great bands each and every night.
Local Expert tip: Swing by the gift shop and pick up a souvenir on your way out.
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. If you're feeling peckish, they have light snacks, as well as meat and cheese plates. 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 Live Music because: This classy venue is stepping the traditional music scene up a notch!
Claudia's expert tip: Happy Hour includes 2-for-1 specials on hand-crafted specialty cocktails.
At Irish Kevin's, hilarious entertainers (particularly Pauly from New York) persuade patrons from the street with a chant of "come on in!" The live performers have patrons dancing, singing and entering drinking contests. Music starts most mornings by 10:30 a.m. and goes non-stop until closing time. Most people stop by for a song or the comedy act and end up staying the night. You have to a have a thick skin to go – they do heckle the audience a bit, so be prepared to be a target of a joke or two. Don't forget to pick up a souvenir shirt with their famous quote: "I came, I drank, I don't remember!"
Recommended for Live Music because: Enjoy the bawdy humor of the musicians at Irish Kevin's where they interact with the crowd, keep the party going and cold beer flowing.
Local Expert tip: Bring your sense of humor. If you're easily offended, this is not the spot for you.