Key West Live Music

Many Key West Bars promise Live Music but the fact of the matter is they have one or two house bands that play the same old Caribbean/Jimmy Buffett/ Bob Marley style music and cater to the tourists who will come once and leave forever. The Rum Barrel offers a different take on Key West Live Music. We import quality musicians with original music from all over the world to perform on the outdoor Quarterdeck Stage. Artists like Bo Bice (American Idol Runner-Up) and the legendary Larry Baeder have graced our stage and created lasting musical memories for all our local Conchs and vacationing patrons.

Rum Barrel specializes in providing original musicians that transcend genres, generations, and stereotypes of what a typical “bar band” should be. We cordially invite to visit our Quarterdeck on almost any night of the week to experience incredible vibes and musical culture while sipping on an Original Mojito and sampling some fresh Key West Seafood.

In addition to our nightly musical offerings, the Rum Barrel is also a major partner with the Key West Songwriters Festival. During the spring each year, legendary musicians gather in Key West to perform for an entire week. Every year, Rum Barrel hosts some of the best acts in the Songwriters Festival on our outdoor stage. For more events and nightly performances check out the Key West Live Music Calendar to see who’s up next…


Thursday, May 2, 2013 the Rum Barrel will host Key West Songwriter’s Festival! Free event – join us! 8:00p – The Shuggah Pies 9:00p – Brian Davis & Bri Bagwell 10:00p – Joey Hyde, Ryan Hurd, Aaron Eshuis & Matt McGinn … READ MORE

Photo of Key West Bars with Live Music
November 21, 2012 Featured Artists Live Music

Mixing the roots of rock n roll, blues, and alternative music, Shaun Peace has a uniquely blended sound of acoustic and electric music that has been cultivating since his days as a young boy. Born in Texas, but moving several … READ MORE

It’s a HUGE weekend at The Rum Barrel! Check out our stellar line-up! Jimmy and the Parrots – November 2, 2012, at 7 p.m. Jimmy and the Parrots From the West Indies and Jamaica to cities all over the U.S., … READ MORE

October 11, 2012 Featured Artists Live Music

KEY WEST, Fla. (October 10, 2012) — Reggae band Chillakaya brings its rich blend of reggae culture and creative vibes from Jacksonville by way of Antigua to Key West. Chillakaya The band will perform on the Rum Barrel Quarterdeck on … READ MORE

September 27, 2012 Featured Artists Live Music

The Personal Legend Made up of Brazilian guitarist, songwriter and vocalist Luciano Souza Menezes and singer, songwriter, and acoustic guitar player singer, son writer, and acoustic guitar player Ibere Maravalha Fortes, The Personal Legend is a blend of Menezes’ classical … READ MORE

August 20, 2012 Featured Artists Live Music

Take one slightly insane cult-icon folk singer, mix in a zany old school saxophone player, simmer nine months, season to taste, let stand three more months, then come up with a cool name and you have Rock Solomon. He performs … READ MORE

LoFi’s with Anthony Picone Anthony Picone is the lead vocals and guitar bass for the LoFi’s, a 3-piece rock band that performs throughout Key West and the Keys. With Tony “Baltimore” Durante on lead vocals and guitar and Dave Baron … READ MORE

KEY WEST, Fla. (April 23, 2012) – The Key West Songwriters Festival is the largest festival of its kind in the world, featuring five days of over 20 free shows and 100 top songwriters performing at the most popular Key … READ MORE

Photo from GIBlythe Guitarist/producer/songwriter Larry Baeder is a seasoned contemporary guitarist with such an impressive musical past that it’s difficult to do justice with words to his multi-faceted talents and accomplishments. A quick glance his most recent endeavors reflect startling … READ MORE

March 23, 2012 Featured Artists Live Music

Bahama Boyz Also known as Ricks ‘n’ Case, this World Beat/R&B/Rock duo of Keith Ricks and Chris Case are co-creators of the ultimate Key West jam wherever they are. Follow Bahama Boyz on Facebook Hailing from the Bermuda Islands, Keith … READ MORE