There’s just something about the unique energy of hearing live music that really re-energizes the soul. For many, the cancellation or postponement of live concerts during pandemic lockdowns was one of the toughest things to take. But thanks to the continued success of immunization efforts, live music in St. Augustine is back, and better than ever. Ready to rock out again? Read on for the lowdown on when and where you’ll be able to see amazing artists in and around the city. 

Tradewinds Tropical Lounge

Having first opened in 1945, Tradewinds Lounge is one of the longest-running entertainment venues in America’s oldest city. Countless famous artists have graced the stage over the years, including The Platters, The Byrds, and even Jimmy Buffett — who was infamously told by the then-owner not to quit his day job. Today, the venue maintains a robust calendar of live entertainment of every genre, so there’s always something playing.  

124 Charlotte St, St. Augustine, Florida 32084

Milltop Tavern

Originally built in the 1880s, this former gristmill has operated as a bar and restaurant since the first term of the Eisenhower administration. Somewhere along the way, the owners began hosting the occasional live music performance, and never looked back. Today, Milltop offers a local-favorite menu of house-made food and specialty drinks, as well as performances by local and regional musicians seven nights a week. 

19½ St. George St, St. Augustine, FL 32084  

Prohibition Kitchen

The post Great Depression-era ambience of Prohibition Kitchen is a must-see when visiting the city. It’s a particularly inviting place to check out some great live music while you tuck into a plate of satisfying gastropub fare, and enjoy speakeasy-style drinks at the longest bar in town. The balcony-level seating area is an especially cool place to relax, as you’ll have a peach view of both the stage below and the 400-year-old pine ceiling. 

119 St George St, St. Augustine, FL 32084

Stogies Jazz Club & Listening Room

Jazz is America’s most celebrated native art form, and there’s no better place in town to experience it than Stogies. Subdued lighting, an outdoor patio and leather sofas give it an exclusive club feel, and seven-days-a-week live jazz and blues means there’s never a bad time to visit. Order a vintage port from the fully-stocked bar, and be sure to ask your server which of the ever-rotating cigar selections from their humidor would pair best with the tunes. 

36 Charlotte St, Saint Augustine, FL 32084

Colonial Oak Music Park

Tucked away beneath a huge tree in the Colonial Quarter, the aptly-named Colonial Oak Stage is an off-the-beaten-path 175-seat outdoor amphitheater that’s worth seeking out. It hosts year-round live music beneath the outstretched branches of the eponymous botanical behemoth, which is charmingly strung with lantern lighting. In addition to local and regional artists of note, the stage also features regular new-talent open mic events. 

21 St. George St, St. Augustine, FL 32084 

Arnold’s Lounge

Arnold’s is a St. Augustine institution — one with a ‘50s style reminiscent of the “Happy Days” hangout that shares its name. It’s a locals’ favorite thanks to its welcoming atmosphere, and the fact that it consistently delivers the “live music, food, fun & spirits” promised on the vintage neon sign out front. Dance to live bands every Saturday, become a rock star yourself during karaoke nights, and don’t miss Ladies’ Night on Fridays.   

3912 N Ponce de Leon Blvd, St. Augustine, FL 32084