The desire of the Republican state to regulate the production and sale of food led to the establishment, during the twelfth century, of the Giustizia Vecchia, a magistracy which later developed an authority over the majority of the city’s guilds. The further decision to set a public register of contracts of apprenticeship reflects the ambition of Venetian authorities to regulate and control both vocational training and access to the urban job market, acting as a guarantor between masters and young apprentices. This chapter presents an historical overview of apprenticeship in early modern Venice, examining the development of the city’s legislation on the matter, and analysing a new sample of contracts recorded in the city’s apprenticeship registers during the sixteenth and seventeenth centuries. In particular, we discuss the complex relationship between the general legal framework established by Venetian public authorities and the particular set of norms detailed in guilds statutes. Our analysis reveals that apprenticeship contracts were used to accommodate a variety of situations, including paying for intense training to masked working contracts, while following the general framework provided by state and guild regulations. We then present an in-depth study of apprenticeship contracts from three crafts (goldsmiths, carpenters and printers), chosen for their economic importance, and because they possibly represented different realities in terms of technological specialization, capital (or labour) intensiveness and typology of market. This highlights yet another aspect of apprenticeship in Venice: the influence of guilds. Some guilds such as the Goldsmiths, were more closed to foreigners, favouring Venetians instead. Apprenticeship in early modern Venice is an institution which, despite appearing as highly regulated and formalized, accommodated a variety of realities with remarkable flexibility.