European emigration towards America, along with the opportunities it offered, reached an unprecedented scale during the 19th Century. Portugueses used to emigrate since the 15th century was part of this flow. In particular, European Portuguese emigrants from Continental Portugal, the Azores and Madeira crossed the Atlantic to Brazil, a country that shared their history, language and customs. The abolition of slavery in Brazil generated the need for foreign labor to work in coffee plantations, which were booming at the time, particularly in Sao Paulo. We will be studying Madeiran emigrants, often confused with continental Portuguese or Azoreans, and their emigration to Sao Paulo at the end of the 19th Century. In the first part, we will be presenting the archipelago to understand the daily life of the insulars and the reasons for their departure, despite governmental efforts to implement an effective legislation and its determination to prevent the scattering of its population. In the second part, we will cross the Atlantic in order to understand the context of the abolition of slavery in Brazil and the difficult implementation of the politics of immigration at the national and local level, which resulted in an influx of immigrants. Amongst these emigrants are Madeirans, whose profile will be analysed in the third part. We have compiled a database from five different sources, which are rarely used together and which will allow us not only to obtain the maximum data on these insulars who left between 1886 and 1899, but, as well, to examine their role in the establishment of Brazilian society and give them a status in the history of Portuguese emigration.