The group was put together by investment manager Peter A. Scott, who in his own words "decided to create an alternative history in which Cuban ska had emerged". He travelled to Santiago de Cuba with Top Cats singer Natty Bo (Nathan Lerner) in 2001 and there they rehearsed and recorded the Ska Cubano album over a two-year period mainly with local musicians including singer Beny Billy (Juan Manuel Villy Carbonell). In late 2004, Scott and Bo decided to go for a less Cuban sound and formed a line-up in London mainly using UK-based Cuban and other Caribbean musicians (three of whom were/are also members of Top Cats, Natty Bo's traditional ska band ). After some experimentation, with Natty Bo as leader and vocalist, the permanent core of Ska Cubano became : Cubans (from Havana) Rey Crespo and Ernesto Estruch, Jesus (Las Tunas), Oreste Noda (Matanzas) and Kico Cowan (Camaguey), together with, from Montserrat, Dr Sleepy (Reuben White), from Spanish Town, Jamaica, Eddie "Tan Tan" Thornton, from Chiba City, Japan, Miss Megoo (Megumi Mesaku) and Londoner Trevor Edwards, with Beny Billy commuting from Santiago for recordings and performances.

In 2006 Venezuelan Carlos Pena gradually took over as co-lead singer, although Beny continued to record and occasionally tour with Ska Cubano. More recently trumpeter Jay Phelps began to perform and record with the band. The second Ska Cubano album, ¬°Ay Caramba!, was nominated for a BBC World Music Award in the "Culture Crossing" category. The album was described as "imaginatively crafted, brimming with melody, wit and a joyous fusion of rhythms, this album's about as much fun as you can have with your clothes on". According to the website all.about.jazz their third album, Mambo Ska, released in May 2010, is "A blast - a raucous, riotous, irresistible blast...high octane party and festival music of the first order".

Ska Cubano have performed at major festivals worldwide including Glastonbury, Big Day Out, and WOMAD, and toured to date, in 30 countries.

In late 2010, their song Soy Campesino was used for the Christmas season adverts for electrical store Comet in the UK.