Best Live music in Key West – Your Ultimate Bar Guide

A Guide to the Best Live Music in Key West

If you’re headed to Key West and haven’t carved out some time to experience its incredible music scene, you’re missing out. This little slice of paradise is about more than just stunning sunsets and key lime pie—it’s a haven for music lovers. From legendary dive bars to open-air hangouts with lively crowds, this island city is packed with top live music venues that are guaranteed to make your vacation unforgettable. Whether you’re into jazzy vibes, trop rock, or jam bands, Key West’s bars have something for everyone. Buckle up; I’m taking you on a musical tour of some of my favorite spots where the rhythm never stops!

Start at the Soul of Key West: Green Parrot Bar

Located on Whitehead Street, the Green Parrot Bar isn’t just a bar—it’s an institution. Known for its free popcorn, gritty vibe, and legendary live music scene, this is one of the best bars in Key West for soaking up daily live entertainment. Expect classic rock, jam bands, and even a bit of New Orleans funk. Sunday soundchecks and Uke Nights are must-sees, where local live musicians gather for unforgettable sessions. Oh, and pro tip? No fancy drinks or blender cocktails here—it’s all about great drinks in their simplest form.

For a Jazzy Escape: Little Room Jazz Club

Looking for something swanky and sophisticated? Head down to Duval Street and step into the Little Room Jazz Club. This cozy hideaway serves up great live music Tuesday through Saturday, offering everything from sultry saxophones to smooth vocalists. Sip on a well-crafted cocktail, enjoy their happy hour (5:30 – 7:30 PM), and lose yourself in an atmosphere that feels like stepping into a 1920s jazz haven.

Hog’s Breath Saloon – A Key West Classic

No list of Key West bars is complete without mentioning Hog’s Breath Saloon. Right at the corner of Front Street and Duval, this hot spot offers a full bar, raw bar, and daily live entertainment from morning till closing time. Their slogan—“Hog’s breath is better than no breath at all”—might just sum up your experience after a long night here. Whether you’re munching on their lobster rolls or grooving to live bands, it’s a fantastic place to kick back and enjoy great food, great drinks, and a lively crowd.

Step Back in Time at Schooner Wharf Bar

If you’re a Jimmy Buffett fan—or just someone who appreciates an authentic, laid-back vibe—you’ll love Schooner Wharf Bar over on William Street. Known for its great service, live music calendar, and quirky two-story setup, this great spot captures the vintage charm of the Florida Keys. They offer two happy hours (morning and evening—hello, early risers!), and it’s a great place to hear Trop Rock legends while enjoying some cool Key West breezes.

Sunsets and Sounds at Sunset Pier

Combine great live music with the iconic sunsets Key West is famous for, and you’ve got Sunset Pier at the Ocean Key Resort. Known for its colorful stools and tropical vibes, this open-air hangout offers everything from smooth acoustic sets to upbeat crowd-pleasers. Trust me, it’s impossible not to have a good time here—whether you’re people-watching, sipping on a mojito, or catching some sun with your toes in the sand.

For Audience Participation Fun: Irish Kevin’s

Right at the foot of Duval Street, Irish Kevin’s is the place where the audience becomes part of the show. This live music scene is notorious for being rowdy, hilarious, and endlessly entertaining. The live bands here interact with the crowd like pros, making every performance feel like a personal concert. Grab a drink from their full bar, enjoy some good time vibes, and prepare to laugh—a lot.

Mallory Square’s Sunset Celebration Musicians

Not all music comes from Key West’s bars. At Mallory Square’s Sunset Celebration, you’ll find live musical performances from incredibly talented street musicians. From banjo players to one-man jam bands, this celebration of local talent is an essential Key West experience. Pair it with a cocktail from a nearby tiki lounge or a snack from one of the food stalls, and you’ve got yourself a magical evening.

Key West Songwriters Festival

Mark your calendar for the next Key West Songwriters Festival, happening in May of 2025. For nearly 30 years, this festival has been a significant part of Key West culture, launching countless careers and showcasing the best of the best. If you’re a true music lover, this is the event you don’t want to miss.

Hidden Gems & Unique Vibes

If you’re in the mood for something a little different, check out these favorite spots:

  • El Meson de Pepe (on Charles Street): The only local salsa band in town will get your feet moving after sunset. Plus, they serve up some of the best Cuban food around.
  • General Horseplay (on Greene Street): With its tin roof ceiling and vintage cocktail vibe, this speakeasy is perfect for a pre-dinner drink and upcoming live shows.
  • Key West Theater (on Eaton Street): If you prefer concert-style live musical performances, this is where you’ll find jam bands, singer-songwriters, and even world-class comedians.
  • Willie T’s (on Duval): Famous for its dollar-bill-covered walls, great drinks, and live performers, this hot spot is packed with both history and fun.

Check out all of our top bars and places to drink – here!

Key West Bars Full of History

Keep an eye out for historic sites tied to Key West’s legendary past as you make your way around. From Ernest Hemingway’s favorite haunts like Captain Tony’s Saloon to the world-famous Sloppy Joe’s Bar, the live music scene here is steeped in the stories of those who’ve come before us.

Plan Your Musical Getaway to Key West

Exploring the best live music Key West has to offer is about more than just drinks and tunes—it’s about experiencing the soul of the island city in the Florida Keys. Whether you’re grooving at the Green Parrot Bar, finding hidden gems like Smokin’ Tuna Saloon, or dancing salsa at El Meson de Pepe, you’ll find something that speaks to your soundtrack-loving soul.

Now, grab your itinerary, dust off your dancing shoes, and get ready to immerse yourself in one of the most unique live music scenes in the country.

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