Published online by Cambridge University Press: 15 January 2020
After the Obama administration (2009–17) began authorizing musical exchanges with Cuba in 2009, Havana's music festivals became a primary site for transnational interactions and a public face for US-Cuban engagement while politicians worked towards normalization in secret. This article uses field research from the Havana International Jazz Festival, interviews with festival participants, and media coverage to explore Cuban music festivals as politically liminal spaces where musical and political life commingled to reflect the changing US-Cuban relationship. While diverse lineups attracted international tourists, artists faced bureaucratic challenges to legally traverse the Florida Straits and create music in the context of intercultural dialogue. Despite these difficulties, Havana as a festival space encouraged musicians to defy genre conventions, explore cultural commonalities, and negotiate social differences on stage during the Havana Jazz Plaza Festival. These transnational interactions culminated in Arturo O'Farrill's album Cuba: The Conversation Continues, which was recorded by US and Cuban musicians in Havana during the 2014 jazz festival and is characteristic of festival exchanges in its representation of a more harmonious international relationship.