Live Music at Sundowners in Key Largo

Live music in the Florida Keys is a natural fit that plays very well with the beautiful weather, frozen cocktails and fresh seafood fare. We all are aware of the live music scene in Key West and especially Duval Street and for sure that is a fun night while visiting the furthermost point of the Florida Keys. But here in the Upper Keys the live music scene is also very popular with many great venues offering an eclectic mix of genres. Country, Reggae, Rock, Folk, and Blues are all available at the many establishments of the Upper Florida Keys.

Upper Keys

There is no arguing the vibe in Key West and the walkability to see several bands is a great selling point and the reason live music fans flock to the area. But here in the Upper Keys we have something that few Key West venues can offer; Waterfront Entertainment. You see most venues, other than the waterfront locations along the Marina in Key West, are landlocked, but here in the Islamorada and Key Largo area most of our venues are located either on the Atlantic Ocean or the Florida Bay and this makes the live music experience so much more enjoyable.

Imagine seeing a great band live riffing Lynyrd Skynyrd’s Freebird and watching the sunset all at the same time. Or hearing your favorite country music ballad while dancing with your significant other under the moonlight of the Florida Keys.

The Upper Keys also offers closer proximity to Miami so venues are able to attract live acts out of the South Florida Area that is easily commutable for these traveling bands.


Sundowners in Key Largo is one of those venues that seems to have it all for a live music enthusiast. In fact Sundowners is becoming the place to go to for live music in the Upper Florida Keys and they are expanding on their live music line up coming this summer.

Located directly on the Florida Bay, the Sundowners complex, which consists of Sundowners, Senor Frijoles and Cactus Jacks has some of the best sunset views in all the Florida Keys. Their live stage is strategically located so everyone has great views of the live entertainment as well as great views of the Florida Bay and the amazing Florida Keys sunsets.

To accompany their live music entertainment, Sundowners Restaurant in Key Largo has been serving sunsets, sandwiches, steaks and seafood on Florida Bay since 1985. You can enjoy the views from their glass-walled dining room, or sit outside on their covered deck, or tropical patio right on Florida Bay. An outside tiki bar is conveniently located on their deck for easy access to drinks and table service is perfect for enjoying a snack or a meal while enjoying all the activities.


Sundowners has been making a name for itself as one of the Florida Keys premier music venues and the bands they have scheduled for the summer will only make Sundowners even more attractive to live music lovers. Here are a few of the headliners that will rock the outdoor stage at Sundowners this summer.

The Regs—The Regs have been performing for over 15 years in local clubs, bars and South Florida Music Festivals from Key West to Palm Beach. The band has BMI Credit for two Albums – “Philth” and “The Regs”. Their original music can be purchased on iTunes, CD Baby and Reverbnation. You will not find a more suitable band for Hard, Classic, Alternative and Modern Rock from one group of experienced musicians. Their brand of music can be heard live most weekends around the South Florida area where they deliver a “Rock Star” show! They typically play 5 to 8 shows per month.

Jay Valor Band— Jay Valor is a breath of fresh air in a musical climate lacking substance. Jay Valor and his band have given South Florida music a run for its money providing quality songs filled with passion and immense attention to detail. From bars to bayous Jay Valor’s songs have touched a variety of music lovers in Florida and beyond. After 4 years of persistence and commitment, Jay Valor released his first EP titled Born to Run. Take a look at Folsom Prison Blues (live studio recording) – Jay Valor – Rockabilly Arrangement – YouTube

Face2Face— Face2Face is more than a Top 40 Cover Band – it’s a local phenomenon created by Anthony Sattel of LoKee Entertainment. The name describes the many faces of the band’s personalities and the collaboration of its musicians. Members of Face2Face have worked with, or currently work with, artists such as Luis Fonsi, Pit Bull, Lauryn Hill, Ricky Martin, Otis Redding, Juanes, Alejandro Sanz, Pharrell, Flo Rida, and the list goes on and on. For over 10 years, Face2Face has been entertaining audiences and creating memories that live far beyond the last song of the evening. A carefully selected repertoire spanning Motown, Funk, R&B, Country, Pop Hits, Dance, and Latin music propel Face2Face to be one of the most captivating bands in the genre of live music entertainment. Face2Face loves playing at venues in the Florida Keys because of the beautiful open air venues and the appreciation of the live music from the crowds that are local or visiting the Keys. Check them out at Face2Face LWM – YouTube

Apache Dragon— Apache Dragon is a professional cover band playing in South Florida and covering genres that include classic rock, hard rock, blues, funk, and a drop of reggae while fusing the core of vocals, guitar, bass, keys, and drums with the pulsing earthly rhythm of the congas. Take a listen at Apache Dragon – Jamdemic 2020 Promo (Covers: Santana, Chris Stapleton, Greg Allman, Beastie Boys) – YouTube

RasPunk— Originating in South Florida, RasPunk is in the perfect place and time to create this new style of music fusion. The band member include Dario Adames (Drums), Gabriel “Militant” Benitez (Keyboard / Vocals), and Kokay (Bass / Vocals), Benji Baez (Guitar). All the members are from different parts of the world; Dario from Venezuela, Militant from Spain, Benji from Haiti and Kokay from Peru. This blend of nationalities, customs, and cultures makes RasPunk stand out in the Miami Reggae scene. This bands goal is to unify the masses by appealing to more than on musical taste, incorporating fans of multiple genres.

Memorial Day Weekend is just a few weeks away and Sundowners has a great line up of live entertainment as a huge kick off to the summer.  The Regs, RasPunks, Jay Valor and Apache Dragon are scheduled for the Memorial Day Celebration. Visit their events calendar for show times at Events at Sundowners – Sundowners Key Largo  and make Sundowners part of your Memorial Day weekend plans.

Great live music at special venues with an amazing atmosphere is what makes shows memorable and what makes live music fans always coming back for more. The live music experience may only last for a few hours, but the feelings and memories will last a lifetime, so be sure to make it a point this summer to enjoy some live entertainment wherever you may be located.