The arcaded façade of the Basilica of Santissima Annunziata, which mirrors the other façades on the piazza

One of Florence's most highly venerated Marian shrines, the Santissima Annunziata was founded in 1250 as the Oratory of Cafaggio by the Seven Holy Founders of the Servite Order. These noble Florentines, following a vision of the Virgin, retired from the city to a hermitage at Monte Senario, north of Florence. The sanctuary's history is intimately connected to a miraculous painting of the Annunciation, still preserved in a chapel at the entrance to the basilica (3). According to tradition, when a fourteenth-century artist, Friar Bartolomeo, struggled to paint the Virgin's face, he fell asleep; upon waking, he discovered the fresco had been miraculously completed by angelic hands. The religious fervor inspired by this miracle ensured the church's inclusion within Florence's fourteenth-century city walls.

The present structure took shape between 1444 and 1477, when Michelozzo began the tribune with its radiating chapels, later completed by Leon Battista Alberti. Toward the end of the 15th century, the height of the nave was increased, and the church was consecrated in 1516.
The exterior features a portico (1) built in 1601 by architect Giovanni Battista Caccini. Above its central arch are traces of frescoes executed between 1513 and 1514 by Pontormo, while the central doorway is crowned by a mosaic Annunciation by Davide Ghirlandaio (1509).

From the portico, visitors enter the cloister (2), known as the Cloister of the Votes ("Voti"), so named because it once housed votive pictures and wax statues adorned with precious ornaments. The cloister is renowned for its magnificent frescoes: Alesso Baldovinetti's work from 1460, Cosimo Rosselli's Calling of St. Philip Benizzi from 1476, and additional episodes from the saint's life painted by the young Andrea del Sarto in 1510. The Life of the Virgin cycle, created in the second decade of the sixteenth century, features works by the era's most promising young artists: Rosso Fiorentino's Assumption, Pontormo's Visitation, and Franciabigio's Betrothal of the Virgin. Between 1511 and 1514, Andrea del Sarto contributed the Nativity of the Virgin and the Arrival of the Magi.

The breathtaking interior features arches and piers sheathed in colored marble (16th and 17th century) and a golden ceiling decorated between 1664 and 1670 to Baldassarre Franceschini's (Il Volterrano) design, who also painted the Assumption canvas. Between the windows, panels and medallions depict Miracles of the Annunciate by various artists.

To the left of the entrance lies the Chapel of the Most Holy Annunciate (3), housing the venerated image of the Virgin. The elegant tempietto enclosing it was designed by Michelozzo and built by Pagno Portigiani in 1448. The adjacent small oratory contains Andrea del Sarto's panel of the Holy Face (4).

The nave's numerous side chapels primarily date from the 17th and 18th centuries, with the Feroni Chapel (5) by Giovan Battista Foggini standing as a jewel of Florentine Baroque. The Tribune (7) features nine chapels, all transformed during the Baroque period. Andrea del Castagno's important contributions include two frescoes: St. Julian in the Feroni Chapel and the Holy Trinity with St. Jerome in the adjacent chapel (6).

Exiting through the door at the nave's left end leads to the Cloister of the Dead (8), constructed around 1453. Above the door is Andrea del Sarto's celebrated Madonna del Sacco fresco (1525) (9). The other lunettes contain an interesting but heavily damaged fresco cycle of the Servites of Mary, painted in the early seventeenth century by Bernardino Poccetti and contemporaries.

The cloister houses the Chapel of the Company of St. Luke (10), which served as the Painters' Confraternity headquarters until 1563, when Cosimo I transferred it to the Academy of the Arts of Design. The chapel's ceiling features Luca Giordano's Assumption fresco, while the high altar displays Giorgio Vasari's canvas of St. Luke Painting the Virgin. Works by Bronzino, Pontormo, and Santi di Tito adorn the other walls.