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Key West Time
October 6th
9:54am · 81°F
 
 

Finding Great Live Music in Key West

"Music hath charms to soothe the savage breast. To soften rocks, or bend the knotted oak."
-William Congreve



 

Nothing lifts the spirits and sets the mood like live music. Of course, numerous cities in the US are well known for their thriving music scenes. New Orleans, Nashville, Austin, and Memphis come to mind. But you would be hard-pressed to find a town the size of Key West offering such a wide and varied selection of live musical entertainment.

While you are enjoying your stay at your VHKW Vacation Rental you will definitely want to go out to experience the fun, camaraderie, and levity of our live entertainment venues.  And the options on this little island are nearly endless!

You can spend a lazy afternoon in one of the island's open-air bars listening to guitar strumming troubadours in the Jimmy Buffett mold. When evening rolls around, seek out the soundtrack for your sunset with some salsa or calypso music, or maybe some lilting steel pan Caribbean tunes.

Then after sundown, the real fun begins. Maybe old-school roadhouse rock and roll gets your blood flowing. It will be easy enough to find plenty of options there. Key West's ample stock of talented rockers is augmented regularly by visiting touring bands, so the scene refreshes itself on an ongoing basis. Many of the local watering holes are the genetic descendants of the famously rough and rowdy shrimpers' bars of the old days. But where once you might have gone looking for a fight, these days everyone is just looking to have a rocking good time. As the night progresses, and everybody gets a few drinks under their belts, look for the ambiance to grow looser, louder, happier, and more immersive as revelers join in singing along with the band or dancing with abandon. Many of Key West's bars stay open until 4 AM, so there's a good chance the revelry will outlast you!

If you are a blues aficionado, you'll be able to choose anything from a traditional delta-style singer with a slide guitar to a hard-driving electric blues band. Similarly, country music fans can find a guitar-slinging cowboy (or cowgirl,) or a real back road honky tonk combo guaranteed to get you doing the "Boot Scootin' Boogie" all night long.

 



The establishments offering musical entertainment are numerous, often with another one right next door. So, on beautiful seasonal nights, you'll see the crowds spilling onto the sidewalks as the partying flows from one spot to another. The legendary "Duval crawl" is very much a real thing, and it happens every night.

If your style is a bit mellower, maybe you'll opt to groove to a nightclub/cabaret performer at one of several lounges and restaurants around town or find some swinging jazz in a traditional jazz club.

The bar, restaurant, and lounge spots we'll recommend generally offer live music 6 or 7 nights a week. Most of their respective websites maintain calendars where you can check to see who will be playing when.  We will link each one as we list them below.

In addition to these places where you'll find performers on an everyday basis, Key West boasts an array of venues where the schedules are event-driven. These include all sorts of concerts as well as comedy shows and theatrical events, often featuring well-known national acts. By their very nature, these events will involve the luck of the draw for the time frame of your visit here. We'll link those venues as well, and who knows- maybe shows by some of your favorite performers will coincide with your time here.

So, let's do the Duval Crawl!

We'll get started by visiting the Historic Seaport District, the area with the densest concentration of live music venues.

 



Billing itself as the "last little piece of old Key West", the Schooner Wharf Bar sits perched right on the dock in the very center of the old seaport. The mostly open-air bar area features the bandstand where the live entertainment begins at Noon (10 AM on Saturdays) and goes well into the morning hours. Sit and savor the music or let your hair down and dance the night away.

Heading around the Waterfront, as we approach Mallory Square, we find Sunset Pier. This amazing bar sits on the Gulf's edge adjoining Ocean Key House at the foot of Duval Street. Here, you are presented with a wide-open, unobstructed view of the sunset over the water. Upbeat performances by solos, duos, and combos start daily around 1 PM and continue until after the sun goes down. Wind down from a bust day of Key West exploration or get yourself warmed up for a big night on the town as you relax over a beer or a delightful tropical drink.

Right next door, in an ancient waterfront warehouse, you can take in a true Key West experience. The patio bar at  El Meson de Pepe serves up live salsa music along with their authentic Cuban food. This outdoor space opens directly onto Mallory Suare where the legendary Sunset Celebration punctuates your day on a high note. The spicy Latin music frequently inspires impromptu dancing and is always sure to get you into a real island mood. Hot, hot, hot!

 



Tucked into the corner of Front and Duval Streets, the Hog's Breath Saloon serves up live music with a nod toward Nashville. Since 1988, this congenial bar has attracted locals and visitors alike while asserting its philosophy that "Hog's breath is better than no breath at all."
In 1997, Hog's Breath was a founder of the Key West Songwriter's Festival, and continues to be an anchor for that annual festive event. This Springtime event has grown exponentially in popularity year by year and offers a rare chance to hear songs you probably know performed by the songwriters who actually penned them.

From there, we head down Duval Street. One block in, we find ourselves at the famous landmark bar, Sloppy Joe's. This is, admittedly, a pretty touristy attraction, but the live music is always top-notch, and plays from Noon until they roll up the sidewalks in the wee hours of the morning. Sloppy's is firmly rooted in Key West history. The bar first opened in a different location half a block away on the very day prohibition was repealed in 1933. Four years later, when the landlord tried to up the rent, they moved to the corner location where they have been ever since. The first location, just a few doors down Greene Street, continued to operate as a bar, and it ultimately became Capt. Tony's Saloon. Steeped in history, this bar was reportedly the favorite hangout of Ernest Hemingway and countless other Key West characters. A cool and dark respite from the hustle and bustle of this busy neighborhood, Tony's offers live music throughout the afternoon and evening hours.

 



Let's head on down to the next corner, Duval at Caroline. And keep in mind that we are highlighting music venues that we particularly enjoy ourselves, know from their reputation, or have had our visitors comment on. The music scene is so rich here, that there will be spots between the ones we suggest, including several on this block so follow your ears and see if something draws you in along your way. For example, halfway down the block, duck down the little alley known as Charles Street, and check out the Smokin' Tuna Saloon. The music here starts at noon with solo or combo acts, continues through the 5 PM happy hour, and then breaks into smokin' rock and roll at 9 PM. You can check out the acts live, in real-time on the TunaCam to get a taste of what you'll be in for when you stop by for a visit.

Continuing down Duval, when we reach the corner at Caroline Street, we encounter the big triple-level bar, The Bull and Whistle. On the ground level, The Bull's many gaping windows open onto the sidewalk and the live music spills out all day and well into the night. A rotating roster of individual performers and bands keeps the energy flowing at this classic island watering hole.

Only a couple of doors down Caroline Street, General Horseplay promises a heaping serving of "tomfoolery" along with their food, topnotch libations and rocking music performers. Loud, loose, and crowded, this is the bar you want if you're looking to really let go and have an exhilarating, fun, wild night on the town. The bands generally start around 9 pm, and then rock 'til they drop!

Two doors down Caroline Street you'll find yourself at Hank's Hair of the Dog Saloon. This open-air bar features mostly troubadour-style solo acts, with an occasional band thrown into the mix. The relaxing ambiance allows you to relax into an easy groove without punishing your eardrums. Music goes from 1 PM until 11:55 each night. (Due to the open nature of Hank's, the amplified sound must wrap up before midnight.) This unique establishment is dog friendly and offers the unusual feature of an onsite food truck as well as its own freestanding bar.

 



Continuing two blocks down Duval brings us to the Downtown Old Town area. We soon come upon Willie T's, a partly outdoor restaurant and bar. The live solo performers here kick off at 11:30 AM every day and go straight through to 1:30 AM. The location, perched right over the sidewalk at the heart of Duval, makes Willie's a perfect spot to catch some tunes as you refresh yourself and watch the never-ending parade stroll by.

Our next stop, just one block off Duval at the corner of Southard and Whitehead, is perhaps Key West's most iconic bar. The Green Parrot first opened in the 1890s as a grocery store that happened to serve liquor in the back room. Even then music figured into the scene. Musicians of Latin and Caribbean descent gathered here to jam together and entertain the patrons. Over the years, with a few changes of ownership, and a name change or two, the party kept on going. In the 1920s and early '30s, Prohibition may have slowed that party down a bit, but it sure didn't stop it. To this day, the Parrot stands alone as a brass-tacks, no-holds-barred gathering spot for locals as well as visitors who return year after year. The wide-open windows spill music into the street and entice you in. From 5:30 to 7 in the evening, the immensely popular Sound Check performances get the room warmed up for the all-out nighttime shows to follow, beginning at 9 PM. Some of the very beat local and touring bands always manage to tear the place up and guarantee a great time for all.

The official motto of this atmospheric treasure says it all: "No Snivelling" (and yes, they spell it just this way.) Once you experience the good vibes and jovial sense of community here, you're sure to be hooked.

 



Now let's take a slight detour into the historic Bahama Village neighborhood. Head down Petronia Street to Andy's Cabana for a major dose or authentic Key West color. This little jewel of a garden bar and performance space offers up a wide spectrum of local and visiting performers. You'll encounter everyone from old timers who have been playing on the island for decades to young folks just beginning to hone their crafts. Open stage nights allow anyone to share their talents, and often offer up delightful surprises.

Next, head back over to Duval Street for something entirely different from anyplace we've visited before. The Little Room Jazz Club serves up top of the line jazz and swing with a dash of classic American Song Book and show tunes sometimes thrown in. Starting up at 8 PM Wed. Thru Sunday, some of this town's finest musicians will lighten your mood and keep you entertained in this elevated jazz club atmosphere.

 



Just a few blocks down, we enter the Uptown area of the Duval corridor. Here we'll visit the classic hotel complex LaTeDa. Just inside the lobby is their classic Piano Bar. In this sophisticated, relaxed environment, the focal point is the corner stage featuring a classy white Grand piano. Enjoy traditional musical fare including outstanding intimate vocal and keyboard performances from 8:30 to 11:30 each evening.
You'll want to book ahead for the shows at the Cabaret Showroom upstairs, where you'll experience stellar live performances by a steady roster of first-class cabaret performers of a variety of different stripes. The showroom and bar open at 8 PM, and the shows begin at 9 PM sharp. A great time is sure to be had by all!

Special Event Concert Venues

 



In addition to the many establishments that offer daily and nightly live musical performances, our little island home also has some larger venues where you will find exciting concerts by a variety of musical performers, including some pretty big acts.   Check the websites linked below to find out what may be happening while you are here, and purchase your tickets in advance.

The Coffee Butler Amphitheater is a City of Key West municipal facility situated in the stunningly beautiful Truman Waterfront. In typical amphitheater style, seating is available on the grassy lawn as well as in the usual seating closer to the stage. Check out their Event Calendar often as new concerts and other special events are added as the season approaches.

After two decades sitting vacant, the historic theater at 512 Eaton Street has been restored, refurbished, and reopened as the Key West Theater.  This spacious and comfortable performing arts center now offers a constant stream of musical and comedy shows, as well as various theatrical productions. With great acoustics, flexible seating, and a full bar to boot, this is truly a comfortable place to enjoy a show of your choice. Check the performance schedule for a show that appeals to you, and ENJOY!

Please keep in mind that there are many, many more options for live music in Key West than just the favorites we've listed here. Please check out some of these, and then explore on your own.

Now, Let the Music Play!


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