There are several reasons why you absolutely must visit the Basilica della Santissima Annunziata. First of all, because it is the most important Marian sanctuary in Florence. It can be said that the church was built around a 13th-century fresco, the Annunciation, which was considered miraculous: legend has it that the painter who was assigned the work wasn't able to paint Mary's face. He suddenly fell asleep, and the fresco was miraculously completed by an angel.
But this basilica is also the Mother House of the Servite Order, a Florentine Order born from the will of seven Florentine nobles who after having distributed their possessions to the poor, devoted themselves entirely to the cult of the Virgin. The church took on the form you see now thanks to subsequent interventions, first in the 15th and then in the 17th century. If you go along the right side, you'll notice the robust octagonal body from the fifteenth century, preceded by and next to chapels from different ages.
Once you pass through the door that opens under the elegant sixteenth-century portico of the façade, you don't enter the church but unexpectedly enter the Chiostrino dei Voti, or Cloister of Vows, so called because of the many ex-voti that were once left here as an offering to Filippo Benizi, one of the Order's founders and a highly venerated saint in the city. The cloister is a light and elegant structure that was designed in the mid-1400s by Michelozzo and presently covered by a large window.
If you look up at the lunettes you can follow the initial stages of the artistic period known as Florentine Mannerism: here you can admire the cycle of frescoes of the Stories of the Life of Mary and San Filippo Benizi painted around 1520 by Andrea del Sarto and his two most famous students, Pontormo and Rosso Fiorentino. This work of art is so important that it marked the advent of a new era of Florentine painting.
I'd especially like to point out the fresco that depicts The Assumption of the Virgin by Rosso Fiorentino, where you can sense the influence of the printed works of the Nordic masters. If you look closely, you'll notice a small illusionist touch in the scene, with the mantle of one of the apostles going beyond the bottom margin of the painting.
FUN FACT: the lamps of the miraculous Annunciation Chapel needed a lot of oil. On the morning of the second Sunday of Easter, a very picturesque procession would take place: a parish priest would lead a donkey carrying two barrels of oil and a small baby dressed as an angel on its rump. It was called "La Cerimonia dell'Angiolino", or The Ceremony of the Little Angel.
