Where to Find the Best Live Music in Key West

No musician better embodied the “island escapism” aura and laidback lifestyle of Key West than the late singer-songwriter Jimmy Buffett. When he moved to our island in 1971, Buffett summed up his passion for his new backyard by writing “I Have Found Me a Home,” with lyrics that describe riding his old red bike to “the bars and the beaches of my town.” 

The island’s vibe and its loony characters helped inspire many of Buffett’s most enduring songs, including “A Pirate Looks at 40” and his best-known hit “Margaritaville.” Before he gained lasting fame pioneering the musical genre now called “trop rock,” Buffett sang and played guitar at Key West hotspots such as the Chart Room, Captain Tony’s, Blue Heaven and the long-gone Full Moon Saloon, where ’70s renegades and visiting celebrities shared drinks and swapped stories.

Music has been a significant part of Key West culture for more than a century — well before Buffett washed up on our shores. Today it continues to be a huge part of what makes Key West an attractive place for tourists and locals.

Our vibrant island city is known for its lively atmosphere, beautiful sunsets, and a rich musical heritage. The live music scene is a blend of genres, with influences from rock, blues, jazz, reggae and more, making it a hotspot for music lovers. If you're looking for the best live music Key West has to offer, Historic Key West Vacation Rentals offers a guide to some of the top venues and events that will ensure your nights are filled with unforgettable tunes.

Iconic Venues for the Best Live Music in Key West

● The Green Parrot Bar: This cornerstone of the Key West music scene has been a favorite for both locals and visitors since 1890. Known for its laid-back vibe and eclectic mix of live performances, this iconic venue hosts a wide range of music from rock and blues to reggae and jazz.

The Green Parrot is not just a bar, it's an institution. Now in its 10th consecutive year of being voted Key West's “Best Live Music Venue” by the Keys Weekly People's Choice Awards, as well as topping lists from Zagats, Southern Living, Playboy and others, The Green Parrot continue to set the standard for free live entertainment in Key West.

● Sloppy Joe’s Bar: A staple of pulse-pounding Duval Street, this hotspot has been serving up live music and good times since 1933. This legendary bar, once frequented by Ernest Hemingway, offers live performances every day of the week. With a lively atmosphere and a diverse lineup of bands, Sloppy Joe’s is a great spot to enjoy rock, country, and everything in between. The bar’s rich history and vibrant energy make it a key player in the live music Key West scene.

● El Meson de Pepe: Located within Mallory Square, this family-owned institution is the island’s top destination for authentic Cuban food. At sunset, El Meson de Pepe gets into the Sunset Celebration action in Mallory Square with the only local salsa band on the island. Come enjoy the open air and samba at sunset to the rhythm of the music and enjoy one of the most beautiful views on the island.

● Hog’s Breath Saloon: This legendary venue has been a part of the Key West music scene for decades. Located just off Duval Street, Hog’s Breath offers live music every day, featuring a mix of local talent and touring acts. The saloon’s rustic charm and lively crowd make it a great place to catch some live tunes while enjoying a cold drink. Their slogan, “Hog’s Breath is better than no breath at all,” perfectly captures the carefree vibe of this beloved establishment. 

● Blue Heaven: Known for its delicious Caribbean and vegetarian cuisine, alfresco dining, roaming cats and chickens, whimsical décor and a vibrant live music scene, this family-owned venue lights up historic Bahama Village. Known as one of the most casual of Key West restaurants, Blue Heaven gives “hang loose” a whole new meaning.

● Little Room Jazz Club: If you’re a fan of jazz, the Little Room Jazz Club is a hidden gem you’ll want to discover. This cozy club offers live jazz performances in an intimate setting, providing a unique alternative to the more boisterous venues on Duval Street. The Little Room Jazz Club is perfect for a sophisticated night out, where you can sip cocktails and enjoy the smooth sounds of talented jazz musicians.

Unique Experiences for the Best Live Music in Key West

● Sunset Celebration at Mallory Square: No visit to Key West is complete without experiencing this grand party around watching the sun disappear, ending another fabulous day in paradise. Every evening, as the sun sets over the Gulf of Mexico, the Mallory Square comes alive with street performers, artists and musicians. The live music ranges from solo guitarists to full bands, creating a festive atmosphere that captures the spirit of Key West. This daily event is free and open to everyone, making it a popular spot for both tourists and locals.

● Key West Songwriters Festival: One of the biggest music events of the year, the Key West Songwriters Festival brings together more than 200 performers for five days of live music. Held every May, this festival showcases some of the best songwriters from around the country, performing at various venues throughout the island. The Key West Songwriters Festival is a unique opportunity to hear the stories behind the songs!

● Fantasy Fest: While primarily known as a wild costume festival, Fantasy Fest also features a plethora of live music events. Held annually in October, this 10-day celebration includes street parties, parades, and numerous live music performances. From local bands to well-known acts, Fantasy Fest offers a diverse lineup of live music that caters to all tastes.

Whether you’re exploring iconic bars, enjoying sunset performances, or attending one of the many music festivals, there’s always something happening in our vibrant island city. If you dream of enjoying a stay in paradise, living the island life like a local, peruse Historic Key West Vacation Rentals’ diverse inventory here.

Once you’ve booked your home away from home, tap into our Concierge Services to pull it all together. Our team is a group of experienced, friendly and knowledgeable specialists who can elevate your Key West experiences!