The festival started in 1980 at Mayport and was held in the fall at various venues in its early years. It switched to the Memorial Day weekend slot and was staged in the streets of downtown starting in 2009.
The 2020 festival, which was to have featured Jeffrey Osborne, the Ron Carter Quartet, Mindi Abair and the Kurt Elling Quartet featuring Danilo Pérez, was canceled in mid-April due to the coronavirus pandemic. The 2019 fest featured Gladys Knight, Brian Culbertson and Kirk Whalum.
The festival has drawn some of the biggest names in jazz over the years. Dizzy Gillespie played at the first one, and Tony Bennett, Diana Krall, George Benson, Miles Davis, Al Jarreau, Diane Schuur and Mavis Staples are among the stars who have played at the festival.