João Gonçalves Zarco (re)discovers the island of Madeira officially on July 1, 1419 or 1420. Around Ponta de São Lourenço, anchor in Machico bay, as this constitutes a protection, where they spent the night and only disembarked in the following day. The island was covered with dense trees, from which the toponym named by the captain comes from. After the first reconnaissance of the Machico valley seafront, a meeting was held to plan the best way to identify the rest of the south to west coast, opting for the use of boats, leaving the caravel anchored in the bay, with fear of probable shallows and currents.When the discoverer passed through a “valley of beautiful groves” on July 3rd, he found old cedars that had fallen by the time, with which he had a cross made, which he had placed on top of a tree, naming the place Santa Cruz. Currently, in the middle of Praça Manuelina (Praça Dr. João Abel de Freitas) there is a cross. Apparently, the column is a reuse of the shaft of the column in marble, from the 18th century. XVI, which once stood beside the axial façade of the Igreja Matriz, recalling the place where the tree that served as support for the standard cross of Zarco stood up, and which was knocked down by a typhoon in 1889. The cross must date back to from the 19th century.

It was only at the beginning of the 16th century that the first houses with tile roofs and two-storey houses appeared in the locality, belonging to wealthy people, and the current Town Hall is one of the first two-storey buildings to appear in the recently created town of Santa Cruz (1515). Today this building, in late Gothic / Manueline language, is a national monument, as it is one of the rare buildings where, since its foundation, the city has continued to function.

A person who stood out in the social and economic life of Santa Cruz was João de Freitas, a nobleman from the house of Duque D. Diogo (brother of D. Manuel I) married to D. Guiomar de Lordello. Returned in 1511 from North Africa, where he fought valiantly against the Moors, he was a trusted man of King Manuel I and for that reason he will be the recipient of the Santa Cruz area Farm, of the lucrative sugar trade, and even the town to possess a customs office for the collection and export of “white gold”. It is he, in effect, who is going to persuade the monarch to give the status of municipality to that locality and it is even in his own houses, where the first councilor of the town is held. It is thanks to this personality that the locality is elevated to a town on 25 June 1515, dismembering from the Captaincy of Machico. The following year, he buys a building, on the ground floor, which he orders for a manor house, a property that has come to our days and where the Paços do Concelho continues to function today.

The Royal Charter of the creation of the town dates from 25th June 1515 and its charter, which effectively constituted the locality in an authentic municipality, dates from 15th December 1515. This separation from Vila de Machico will not, of course, please the Captain-Donate and the councilors of the respective municipality who are going to oppose such claim, and the Captain even refused to receive the presentation of the Letter to the City Council of Machico. The area of this new municipality of Santa Cruz was separated from Machico from Porto do Seixo to the end of Caniço, also covering a small territory of the Captaincy of Funchal - the lands of Caniço located west of Ponta da Oliveira.

It is also due to this prominent personality, João de Freitas, the construction of the Igreja Matriz de Santa Cruz, being responsible for the progress of the works, and he is also at the origin of the founding of the local Santa Casa da MisericórdiaHospital, which it has come to our days. His slab tomb in Flemish taste, with bronze blades bordering the lid, can still be seen today in the main chapel of the Igreja Matriz. His son Jordão de Freitas, who was Captain-Major of the Armed Forces of the Kingdom and Lord of the Moluccas Archipelago, offered a peace holder, in gilded silver with precious stones, to the Igreja Matriz, which is now located in the Quinta das Cruzes Museum , already presenting a Renaissance grammar.

Thanks to the successful planting of sugar cane at the end of the century. XV, also in the Santa Cruz area, the foreign middle nobility, mainly Italian (to put the names in Portuguese) who come in search of the flourishing production and lucrative trade of sugar. An example of this is the opulent Urbano Lomelino who settled in Porto de Seixo with a house and mill, later founding, by pious testamentary disposition, the Convent of Nossa Senhora da Piedade de Santa Cruz. Urbano Lomelinowas married to Joana Lopes but died childless, which is why his nephew, Jorge Lomelino, married Maria Adão, who will effectively build the monastery. Among other artefacts, a precious Flemish painting, dedicated to Nossa Senhora da Piedade, which can be found in the Museum of Sacred Art in Funchal, after having been through some rocky vicissitudes, remains today from the convent's estate. In the painting, on the steering wheels, its donors are represented. Other pious legacies that this merchant and sugar producer left was the obligation to send out, every year, to say mass in a church in Genoa, his birthplace, and where his mother rested. His tomb, in Manueline style, is found today in the Chapel of NossaSenhora da Piedade of the Quinta das Cruzes Museum.

Another example is the no less opulent, Nuno Fernandes Cardoso who is going to settle in Gaula, building a Solar and chapel of S. João Latrão, which has reached our times. Married to Leonor Dias, he will even send his children to Italy to study and to be intermediaries in the Madeiran sugar trade. Among other liturgical objects, this chapel has a precious and interesting Flemish altarpiece, dedicated to Nossa Senhora da Misericórdia, and which is now found in the Museum of Ancient Art, in Lisbon. On the central panel, kneeling in adoration, the donors are also represented.

Or, still, the sisters Isabel and Leonor Álvares, who established the Chapel of the Mother of God, in Caniço, initially built with the purpose of constituting itself as the chapel of a small convent. The original Mannerist altarpiece, which incorporates precious paintings by Diogo Contreiras, one of the most interesting Portuguese painters of the Mannerist period, stands out in this hermitage with Manueline grammar.