The paper studies the medieval tradition of the 9th century al-Khwarizmi’s handbook on algebra compared with its Latin translation by Gerard of Cremona (made in Spain, around 1170), later translated in Italian vernacular by an anonymous Florentine abacus master, during the 14th century. This long journey along five centuries and three countries deals accurately with the mathematical contents; by means of analysis of explicit and implied elements in the three works, we also focus on the different historical backgrounds, the social condition of the authors, the cultural, mindset-related and religious obstacles they had to take into consideration, while disseminating these calculation techniques, and, finally, their teaching style.