Recent archival research has confirmed that Santi, son of Tito di Santi di Bartolomeo dal Borgo a Sansepolcro (enrolled in the Arte dei Linaioli in 1535) was in fact born in the Florentine neighbourhood of San Michel Visdomini on 5 December 1536, and not in Sansepolcro, as was previously thought (A. Belluzzi, G. Belli, La villa dei Collazzi, Florence 2016, p. 46). In addition to his birth, as studies on the artist progress, it becomes apparent that Santi was one of the major figures in Florentine artistic circles from the mid-sixteenth century. From his collaboration on the Studiolo of Francesco I de' Medici, for which he painted three works: Hercules and Iole, Phaeton's Sisters and The Crossing of the Red Sea, he revealed himself to be one of the principal exponents of the new climate of expression dear to the young duke, focused on the study of nature, and on the ideas of the Counter reformation. In fact, from the 1560s, artists were increasingly required to adhere to the scriptures and an explicit representation of the passions, but above all to a language that was naturalistic, anti-allegorical, which in Florence too became the principal orientation of the arts. Starting from the Resurrection painted for the Medici chapel in Santa Croce in 1574, Santi di Tito was able to create his own interpretation on the Florentine tradition of disegno, blending it with the new naturalism, ahead of other artistic centres throughout Italy. In this significant painting, the heads of the sleeping soldiers taken from life, or the recumbent bodies in the foreground, displaying their bare and dusty feet to the viewer are examples of these preferences: elements of naturalism developed in an environment that was moving away from Vasari's Maniera moderna and the influence of Michelangelo. These developments were taken further by Santi di Tito in a vocabulary capable of reconciling the tradition of Andrea del Sarto, Raphael's Roman achievements, and also the naturalistic innovations of Zuccari, which he must have encountered on an early visit to the Eternal City. However, his interest in naturalism derived above all from Bronzino, champion of an unambiguous ability to reproduce the tactile qualities of fabrics and animals, of faces and expressions, an ability that Santi di Tito embraced and continued to develop right up to his final works, painted at the beginning of the Seicento.
These features of the artist's style were immediately recognised by the critics of the time, starting with Raffaello Borghini, who, in Il Riposo (1584), identified him as one of the great innovators in Florentine painting, and this was also fundamentally acknowledged by Bocchi in his Le bellezze della città di Fiorenza (1591) and then by Baldinucci in Notizie dei professori del disengo da Cimbaue in qua (1681-1728) which considered him to be the leading exponent of the reformed painting in Florence in his ability to turn a natural and everyday occurrence into an event of supernatural significance, such as the Resurrection, or in this case, the Annunciation.
The present work fits perfectly into the cultural climate described so far, and can be attributed with certainty to Santi di Tito, whose style is evident in the oval faces, with their rose-coloured flesh and sweet, serene features. Also typical is the physiognomy of the Virgin, with her rosy cheeks and face inclined in acceptance of the divine will expressed by the angel. The scene takes place in a domestic interior enveloped in shadow, although the bed and canopy are visible in the background, and also the low chair next to the workbasket: an extremely simple wicker basket, on which the light plays creating chiaroscuro effects entirely in keeping with the innovations of the late Cinquecento. And light is also given the task of unifying the space and the scene, a light that from supernatural - a halo around the angel and the Holy Spirit - becomes natural and allows the paint to record naturalistic effects on the bodies and clothing, or to create dazzling contrasts in tone, patches of light and deep shadow, like the gleam that renders the wall behind the Virgin tangible, or illuminates the golden straw of the chair that acts as a kneeling-stool. And it is light, once again, that regulates and makes plausible the spatiality of the scene with expedients of naturalistic illusionism that now suggest a space that only a few years earlier would have been regulated by rigid perspective. The episode of the Annunciation is thus brought into an everyday environment, domestic and serene, imbued with the change of style that towards the end of the century was to result in painting more sombre in tone, while nevertheless remaining faithful to the simplicity "senza errori" of Andrea del Sarto.
As far as the date of execution of the present work is concerned, comparisons can be made with works representing the same subject, such as the Annunciation in the church of the Compagnia di San Salvatore in Sinalunga, in which a more solid modelling of the faces and bodies seems consistent with other works dating to the end of the 1570s. Closer to the stylistic characteristics of the present painting are the compositional simplicity and luminosity of the Annunciation in the Museo Civico di Sansepolcro, signed and dated 1589. In this altarpiece the kneeling angel surprises the Virgin in the darkened room of a palazzo looking out over a landscape, a work already infused with a stronger light effects than the present Annunciation, which is probably datable to the mid 1590s, just a little earlier than the Annunciation for the Vecchietti chapel in Santa Maria Novella. In that monumental altarpiece executed by Santi di Tito at the very beginning of the Seicento, shortly before his death in 1603, strong and vivid beams of light create deep shadows that barely hint at the space of the room in which the angel encounters Mary, beams of light that pick out the objects with greater intensity compared to the present painting and achieve lighting effects that reveal an awareness of Caravaggesque innovations, and displaying the painterly skills of an artist who was a protagonist on the Florentine and Italian artistic stage during the late Cinquecento.