Covering urban courtyards allows for the creation of interesting public or semi-public spaces, sheltered from bad weather and possibly with a controlled climate. In addition, the use of a transparent or semi-transparent roof allows the advantage of natural lighting. The use of this type of roof is a common solution in the countries of central and northern Europe, but difficult to apply in Mediterranean temperate climates because it would cause overheating for a good part of the year unless appropriate solar control strategies are applied. In this work, a case study of the courtyard of a former Venetian convent was considered. A number of types of partially transparent roofing and some solar control strategies were compared by means of computer simulations. The various solutions were compared from the point of view of visual and thermal comfort, as well as from that of primary energy demand for supplementary artificial lighting and possible energy demand for heating, ventilation and air conditioning if the relative system was present. Given the profusion of this type of courtyard in the Italian territory, its thermal and luminous behaviour was also simulated in the warmer climate of Palermo. The simulation results showed that the better solutions were those based on the use of dynamic solar control devices.