Diego Pinera left Uruguay at the age of 18, he went to the Universidad de arte y musica de la Havana, Cuba. There he got the opportunity to deepen his afrocuban influences on the drums and the timbales. He also got the chance to learn and play with famous Cuban musicians like Enrique Pla (drummer of Irakere) and with newcomer Joaquin Pozo (conga player).
After his time in Cuba, Pinera got hired for one year in a salsa orchestra in Seattle, called Orquesta Cambalache featuring Melcochita on vocals. Back in Uruguay he formed his own trio 'Diego Pinera trio' and recorded the CD 'Buscando' on the Perro Andaluz label.
Later on he received a scholarship to study at the Berklee College of Music in Boston and was teached by Danilo Peréz. There he recorded with Edu Tancredi the album 'Ongoing Dream', featuring Antonio Sanchez, Jerry Bergonzi and Miguel Zenon. In Boston Pinera also recorded 'Schades' from Shimon Ben Shir, produced by Oscar Stagnaro. During this time he also fulfils an engagement for the SHAKIRA Tourband. Unfortuanetly he needed to abort his contract ahead of time because of bad health conditions. Since 2003 he has lived in Berlin (Germany). He has been working continuously with musicians such as Wilson DeOliveira, Andreas Schmidt, Martin Auer, Christian Grabandt, Pepe Berns, Tino Derado, Sebastian Schunke, Daniel Stawinski, Robbie Gerken, Dan Freeman and many more. Pinera also directs two ensembles in the music school Berlin-Mitte along with teaching master classes in various different German institutions. Further more he won first price in the Jazz and Blues Award 2005 with Latin Jazz band 'Clave Azul'.