23 Artworks Not to Miss at the Uffizi Gallery

Simone Martini, Annunciation (1333)

With its ornate carved top, gold leaf, and tempera paint, this large-scale panel painting is considered one of the masterpieces of pre-Renaissance art. Commissioned for a side altar in the Siena cathedral, it features textbook Annunciation iconography: The Archangel Gabriel appears to the Virgin Mary to tell her of the forthcoming birth of Jesus; he holds an olive branch, representing peace; a dove at the top represents the Holy Spirit; white lilies symbolize Mary’s purity. The raised inscription passing from Gabriel’s mouth to Mary’s ear—Ave gratia plena dominus tecum—roughly translates as “Hail, full of grace. The Lord is with you.” Gabriel’s fluttering cloak and spread wings suggest that he has just landed, startling Mary, who shies away, clutching her garment and half-closed book. The prophets Jeremiah, Ezekiel, Isiah, and Daniel are depicted in the tondos set across the top of the altarpiece, and two patron saints flank the Annunciation scene.

Second Floor, A5

Paolo Uccello, Battle of San Romano: Niccolò Mauruzi da Tolentino unseats Bernardino della Carda (c. 1435–40)

One of three panels depicting the 1432 Battle of San Romano (Pisa)—the others are at the Louvre and London’s National Gallery—this scene portrays the unhorsing of Bernardino Ubaldini della Carda, a soldier of fortune who fought for the Sienese against the victorious Florentines. With an earthy palette, the painting is most notable for its innovative use of perspective, in which the battle scene in the foreground is filled with foreshortened figures, a confusion of legs and limbs, and angular thrusts of lances, one of which is toppling Ubaldini from his horse. The background dramatically retreats to an inexact vanishing point and unseen horizon.

Second Floor, A9

Piero della Francesca, The Duke and Duchess of Urbino (1473–75)

Among the most famous portraits of the Italian Renaissance, The Duke and Duchess of Urbino depicts Federico da Montefeltro, a mercenary Duke, and his wife, Battista Sforza, who died following childbirth at age 26. (Actually, she never held the title of Duchess since Montefeltro became Duke two years after her death.) It is likely that the artist worked from Sforza’s death mask, and her pallor is thought to allude to her death more than to her status.

At the time, it was considered beautiful to have a high forehead, so women used to pluck their hairlines. The profile position is a reference to the design of ancient coins, which were popular collectors’ items among the wealthy. Atypically, however, the duke faces left, a design decision that symbolically binds him to his wife but more practically hides wounds from a jousting tournament in which he lost an eye and part of his nose (according to one account, he cut out a chunk of his nose so that he could better see with his remaining eye).

Now in a freestanding frame, the diptych panels were originally joined by hinges so that the whole could close like a book. On the back of the panels, the duke and duchess are portrayed being carried triumphantly on ancient wagons, accompanied by Christian virtues and Latin inscriptions that speak to their moral values.

Second Floor, A9

Piero del Pollaiolo and Sandro Botticelli, The Seven Virtues (1469–72)

Like a virtual Supreme Court, this imposing cycle of paintings depicts the seven Virtues, each bearing symbols of her attribute: a sword, a calyx of the Eucharist, a breastfeeding infant, and so on. All are resplendent in their richly detailed garments and jewels atop their thrones. Six panels were painted by Pollaiolo and one by Botticelli (much to Pollaiolo’s chagrin). Pollaiolo was commissioned by the Tribunale di Mercanzia in Piazza della Signoria, a court that heard disputes between Florentine merchants and administered justice among the guilds. Ironically, Botticelli got in on the commission because of his ties to the Medicis, creating both a business dispute and a guild injustice.

Second Floor, A10

Sandro Botticelli, The Birth of Venus (1485)

You’ve seen her on tote bags, T-shirts, umbrellas, and sundry gift shop items. She has sold Reebok sneakers and inspired artists and designers such as Andy Warho and Jean Paul Gaultier. In early 2023, her head was slapped on the bodies of various female sightseers in a much-derided ad campaign promoting Italian tourism.

Why exactly is Botticelli’s depiction of the goddess of love and beauty so alluring, so symbolic of the Renaissance? The work has an ethereal quality created by the soft, pastel palette; Venus’s luminous skin and long, flowing hair; and the effortlessness with which Venus, blown by the winds of Zephyr and Aura, floats toward the shores of Cyprus. At the same time, the painting’s mythological subject matter reflects the growing interest in humanism during period it was made, and with it an interest in ancient nudes, a marked departure from the prevailing Christian art.

The creation of The Birth of Venus’s sister work, La Primavera, overlapped with Botticelli’s commission to paint three scenes on the walls of the Sistine Chapel, with The Birth of Venus coming shortly after. Botticelli borrowed Venus’s demure pose from ancient sculptures of a “modest Venus” attempting to hide her nudity (see the Uffizi’s own Medici Venus). Later in his career, as Botticelli became more religious, his works declined in popularity. As a follower of Savonarola, he participated in the 1497 Bonfire of the Vanities, in which Christians burned “vanities”—such as art, jewelry, mirrors, and other baubles—that distracted them from religious devotion.

Second Floor, A12

Boar (2nd–1st century BCE)

A popular and widely copied statue, this lifelike marble sculpture by an unknown Roman artist was probably inspired by an earlier Hellenistic bronze. In the entangled tradition of classical statuary, it has subsequently spawned many iterations. Tucked in a corner behind Laocoön (see below) in an area roped off to visitors, it was found in Rome in 1556 on a slope of the Esquiline Hill and brought to Florence in 1568, where Cosimo I de’ Medici had it placed at the Pitti Palace.

Likely part of a group of statues with a hunting theme, the animal depicted is captured in a pose as if awakening to the sound of approaching hunters. Its famous and more accessible descendant is the 17th-century bronze fountain (the “Porcellino”) at the loggia of the Mercato Nuovo near the Ponte Vecchio, replete with a shiny snout from visitors feeding it coins for good luck.

Second Floor, West Corridor (A24)

Baccio Bandinelli, Laocoön (1520–25)

As told by Virgil in the Aeneid, Laocoön was a Trojan priest who tried to warn his fellow citizens that the Trojan Horse was a trick sent by the Greek army. To prevent the exposure, Poseidon or Athena—sources vary—dispatched sea serpents to stop him and to kill his sons as punishment. The original Greek work depicting this scene was found on the Esquiline Hill in Rome in 1506 and has been an inspiration to artists ever since. (It lives at the Vatican Palaces in Rome.) In 1520, Pope Leo X (né Medici) commissioned Baccio Bandinelli to make a copy, and the artist took it upon himself to “fix” the original, replacing the lost upper limbs of each figure and parts of a serpent. But the work’s real power lies in the dynamic movement of the figures, the straining muscles, the entangling serpents, and Laocoön’s agonized expression.

Second Floor, West Corridor (A24)

Piero di Cosimo, Perseus Frees Andromeda (1510–15)

A man flying in the sky with wings on his feet, a giant sea monster with a curlicue tail—this painting stands out for its unusual subject matter and its use of continuous narrative, in which several scenes are depicted in the same work. According to Ovid’s Metamorphoses, the legend of Perseus goes like this: Andromeda is being sacrificed to appease a monster sent by Poseidon, who was angry at Andromeda’s mother, Cassiopeia, for her arrogance. After it swoops in, we see Perseus atop the beast, sword poised to strike, and we see him again in the lower right celebrating his success with his future bride, Andromeda. In the lower left, Andromeda’s family flinches away from the imminent attack, and on the right they are celebrating Andromeda’s rescue.

In The Lives of Artists, Vasari described Cosimo as an eccentric who was a bit of a slob, afraid of thunderstorms, and who subsisted on hard-boiled eggs prepared in large batches because of his fear of fire. Like Botticelli, he returned to religious art after coming under the sway of Dominican friar Girolamo Savonarola, who advocated the destruction of secular art. Historical records reveal that Cosimo died of the plague in 1522.

Second Floor, A28

Leonardo da Vinci, Adoration of the Magi (1482)

This rare unfinished painting by Leonardo allows viewers to get a sense of his working process. It was commissioned in 1481 by Augustinian monks for the church of San Donato, just outside Florence. The painting, which Leonardo was to complete within 30 months, is a complex composition featuring architecture, battle scenes, and numerous figures crowded around the central ones: the Virgin and Child and the three magi. Leonardo wound up leaving Florence prematurely for the court of Ludovico Sforza in Milan. When he failed to return and finish the job, the Augustinian friars commissioned the same scene from Filippino Lippi, who completed his similarly crowded panel painting in 1496.

Second Floor, A35

Raphael, Madonna of the Goldfinch (Before February 1506)

Raphael’s Madonna of the Goldfinch is hung near Michelangelo’s Holy Family, an apt association since they were painted concurrently, when both artists were living in Florence. The painting was a gift for the 1506 marriage of Lorenzo Nasi, whose home was later destroyed in an earthquake in 1547, breaking the painting into 17 pieces. It was hastily put together with obvious seams and other alterations that remained until a six-year restoration was completed in 2008. Similar to Michelangelo’s composition, the figures form a triangle and are in a natural setting. The young John holds a goldfinch, which Jesus reaches out to touch it. The bird was often used in the Renaissance to symbolize the crucifixion because it was said that its red spot appeared when it tried to pluck a thorn from Jesus’s crown and a drop of blood landed on its head.

Second Floor, A38

Michelangelo, Holy Family, the “Doni Tondo” (1505–06)

This relatable arrangement of figures—one parent handing off their child to the other—depicts Mary, Joseph, and the infant Jesus in a pastoral setting. Instead of a stiffly posed Mary and a baby Jesus raising his hand in a gesture of blessing, this child clambers over his parents, grabbing his mother’s hair. The only finished panel painting by Michelangelo to survive, the tondo (a religious painting intended for the home) was made for the Florentine merchant Agnolo Doni on the occasion of his marriage to Maddalena, a member of the powerful Strozzi family.

Like most artists of the time, Michelangelo was awed by Hellenic Greek statues that were being excavated from Roman villas in the early 16th century, as evidenced by the twisting bodies and expressiveness of the figures. Two prominent discoveries, the Belvedere Apollo and Laocoön, had just been excavated as Michelangelo worked on this painting, and the poses of two nude figures in the background are direct references to them.

Second Floor, A38

Hermaphroditus (2nd century AD)

Perhaps it’s a sign of the times that on my last visit, the room containing Hermaphroditus was roped off, keeping would-be vandals a safe distance away. The sleeping figure is contorted, lying on their stomach with head turned to the right and legs twisting to the left to reveal a penis on the otherwise feminine form. This Roman copy of a 2nd-century BC Greek bronze is carved from marble from the Greek isle of Paros. It is one of a number of replicas, the famous “original” being the Borghese Hermaphroditus at the Louvre. As described by Ovid in Metamorphoses (ca. 3–8 AD), the male child of Hermes and Aphrodite escaped at the age of 15 from Crete to Caria (present-day Turkey), where he was seduced by a naiad who prayed to the gods to never separate their bodies again. Other versions have Hermaphroditus bi-gendered from birth.

Second Floor, A40

Élisabeth Louise Vigée Le Brun, Self-Portrait (1790)

Daughter of the painter Louis Vigée and wife of the well-known art dealer Jean-Baptiste-Pierre Le Brun, Elisabeth was a successful portrait painter of royals (including Marie Antoinette), aristocrats, actors, writers, and herself. She painted this self-portrait in Rome after narrowly escaping Paris and the French Revolution. On her way south, she stopped in Florence and visited the Pitti Palace and the Uffizi, where she was particularly impressed by the self-portrait of Swiss painter Angelica Kauffman.

The Uffizi director of the time invited Vigée Le Brun to add her own work to the museum’s growing collection of self-portraits. Hers arrived soon after, in 1791, with a letter explaining it as a tribute to Marie Antoinette and the ancien régime: “I have portrayed myself with palette in hand, before a canvas on which I am drawing the queen in white chalk.” Vigée Le Brun spent a decade in exile, living in Italy, Austria, and Russia before returning to France in 1802. She was among few women to be accepted as a member of the Royal Academy of Painting and Sculpture.

First Floor, C14

Parmigianino, Madonna with the Long Neck (1534–40)

In this painting, the Virgin’s elongated neck and fingers and her gauzy garment revealing nipple and navel create a sensuality not typically associated with imagery of the Virgin and Child. The infant Jesus, also preternaturally elongated, seems to slide off her lap, the pose a foreshadowing of his death as seen in numerous pietàs. More eerily, in an urn held by the leggy angel, a faintly rendered crucifixion appears where the infant’s reflection should be.

In 1534, Parmigianino was commissioned to paint this work for a church in Parma within five months, but it was still unfinished upon his death in 1540. Two years later, it was placed on the designated altar with an inscription added to the base of the column on the right that reads: “Adverse destiny prevented Francesco Mazzola from Parma from completing this work.” St. Jerome is seen in the background unrolling a scroll, his head turned to converse with what would have been St. Francis, but Parmigianino managed to complete only one foot.

The painting is a prime example of Mannerism (from the Italian maniera, meaning “style”), which can be understood as a “stylized style.” According to Vasari, it emphasizes the artists’ intellect and mental conception over naturalism. Mannerist works are often characterized by heightened color, illogical compression of space, and elongated bodies that create a sense of unease. Appropriately, the style arose during a period of social upheaval that coincided with the Reformation, the bubonic plague, and the 1527 sack of Rome by Holy Roman Emperor Charles V.

First Floor, D4

Pontormo, Supper at Emmaus (1525)

Pontormo depicts the story of the resurrected Jesus dressed as a traveler with two of his disciples, who did not recognize him until he made the gesture of blessing and broke bread at dinner, just as he had done at the Last Supper. The work was painted for the monastery where Pontormo took shelter from the plague raging through Florence and where, during his stay, he painted frescoes of the Passion in the main cloister. The monks then commissioned him to make this painting for its guest quarters, the theme resonating with the monastery’s role as a way station for travelers.

Supper at Emmaus is an example of Mannerism, the late-Renaissance style that features asymmetrical compositions and unnatural features (see Madonna with the Long Neck) that, according to Vasari, were intended to create a sense of restlessness and psychological tension, especially when compared with the balance and ideal beauty of the High Renaissance. Inspired by Dürer’s engraving of the same subject, Pontormo added such hallmarks of Mannerism as twisting figures, ambiguous space, and touches of realism such as the disciples’ bare feet and cats and a dog under the table. The divine eye at the top, a symbol of God, was painted after the artist’s death to conceal the original three-sided face representing the Trinity, which was prohibited by the Counter-Reformation.

Another of Pontormo’s works, Deposition From the Cross, can be seen in situ at the Church of Santa Felicita, just across the Ponte Vecchio from the Uffizi.

First Floor, D12

Rosso Fiorentino, Moses Defends the Daughters of Jethro (1523–27)

Pushed to the foreground, the buff male bodies in this raucous scene nearly leap off the canvas, which depicts the biblical story of Moses as a badass. After killing an Egyptian who beat an Israelite woman, he flees to the desert and stops to rest at a well. The seven daughters of Jethro, a priest in the land of Midian, also stop to draw water for their flock. Some shepherds arrive and bully the women, so Moses leaps to their defense and single-handedly dispatches each one. The in-your-face triangular composition has Moses at the apex, whaling away on the shepherds, who lie at his feet in a heap. In the background, Moses is seen racing—awkwardly, his left arm making little anatomical sense—toward Jethro’s daughter Zipporah, whom he would soon marry, as the other daughters run away.

First Floor, D12

Titian, Venus of Urbino (1538)

Reclining nudes were all the rage in 16th-century Venice, and who better to paint one than the renowned Venetian artist Titian, who was known for his ability to render the softness and luminosity of skin. Titian was an artistic prodigy, apprenticing with Bellini at the age of nine. One of his most famous paintings, Venus of Urbino depicts a young bride about to take part in the ritual of il toccamano, in which she would touch the hand of the groom to express consent to marriage. She holds a bunch of roses, the symbol of Venus and love, while the sleeping dog at the foot of the bed symbolizes fidelity in marriage. The maidservants in the background have removed a gold and blue wedding dress from the bridal trunk. The reclining nude is a theme that dates back to antiquity and continues today, though usually with a knowing wink.

First Floor, D23

Caravaggio, Bacchus (1598)

Caravaggio was known for brawling as well as more serious crimes (including murder), but he’s one of art history’s darlings whose name is synonymous with his dramatic style (Caravaggesque) and his followers (the Caravaggisti), He died at age 38 under suspicious circumstances while on the lam, and the theories range from assassination by the Knights of Malta to lead poisoning from his sloppy use of paints.

Caravaggio’s groundbreaking paintings were notable for their dramatic use of chiaroscuro, strong contrasts in light and shadow that made scenes appear theatrical and figures and objects more volumetric. In this painting, he renders the god of wine as a sensuous, tipsy-looking young man wearing a crown of grape leaves and a loosened robe falling from his torso. He offers a brimming glass of wine to the viewer. An arrangement of ripe and rotting fruit below are thought to symbolize either fermentation (wine), debauchery, or a reminder of fleeting youth and inevitable death.

This work was painted in Rome and commissioned by Cardinal Francesco Maria del Monte. Some scholars and contemporaries of Caravaggio variously believe that the figure is a self-portrait, or that it depicts one of the artist’s pupils whom he was involved with and who appears in other paintings, or that the work alludes to the cardinal’s own sexuality and his relationships with the boys under his care. This painting and Caravaggio’s Medusa were given by the cardinal to Ferdinando I de’ Medici on the occasion of the wedding of his son Cosimo II in 1608.

In the same gallery, don’t miss two decadent still-lifes by Empoli of foods that seem destined for a feast and, in nearby galleries, Caravaggio’s Sacrifice of Isaac and Medusa.

First Floor, E5

Gerrit van Honthorst, Supper Party With Lute Player (c. 1619)

This leader of the Dutch Caravaggisti took chiaroscuro to the extreme. In many of his works, light seems to emanate from the figures themselves. In religious scenes, such as the nearby Adoration of the Child, the effect is supernatural. In this painting of a dinner party, it’s more like mood lighting. Everyone at the table is seen having a good time, apparently amused by the action on the right, where a woman holds a candle as she inserts an unidentified object into a man’s mouth. (According to some sources, it’s a piece of meat.)

Honthorst, who combined Caravaggio’s style with Dutch genre painting—depictions of ordinary scenes—encountered Caravaggio’s works while living in Rome from 1616 (possibly earlier) to 1620. After returning to Utrecht, his paintings became more subdued and shed the dramatic lighting. He went on to enjoy great success as a court painter and, with painter Hendrik Terbrugghen, disseminated Caravaggio’s techniques throughout Holland; this would later influence Rembrandt and other Dutch artists. Honthorst’s canvas Adoration of the Shepherds was one of the works destroyed in the 1993 Mafia bombing of the Uffizi Gallery that killed five people and damaged numerous other pieces.

First Floor, E6

Artemisia Gentileschi, Judith Beheading Holofernes (1620)

Perhaps it’s no coincidence that one of the best depictions of this well-known scene was created not only by a woman, but by one who had been raped. The story describes how Judith used her feminine wiles to gain access to the tent of Holofernes, a general in Nebuchadnezzar’s army, which had laid siege to the Jewish town of Bethulia. After a lavish feast featuring plenty of wine, Judith is seen decapitating a drunk Holofernes as her maid holds him down.

Artists have often illustrated this story as a fait accompli, with Judith holding the general’s head, or with sword poised, about to strike. But Gentileschi doesn’t hold back; here, Judith has a tight grip on Holofernes’s hair, the sword is midway through his neck, and blood is spurting. Caravaggio had a great influence on Gentileschi, putting her among the Caravaggisti. (In fact, her earlier version of the same scene (in the Naples Museum) was sold in 1827 as a work of Caravaggio.) But while her composition and figure modeling are direct references to Caravaggio’s painting of the same scene, the expression on Judith’s face seems more tentative in Caravaggio’s and more determined in Gentileschi’s.

Gentileschi was fascinated with this subject and created two versions of this composition and four others of Judith and her maid after the deed. Upon its arrival in Florence, the “virile” work was denied the honor of exhibition. It was only with the help of Gentileschi’s friend Galileo Galilei (the Uffizi owns this nice portrait of him by Justus Suttermans) that she was able to extract payment for the work from Grand Duke Cosimo II de’ Medici, who died shortly after. Among other accolades, Gentileschi became the first woman to enter the Academy of Art and Design in Florence.

First Floor, E2

Justus Suttermans, Madonna “Domenica delle Cascine,” la Cecca di Pratolino, e Pietro Moro (1634)

The Flemish artist Justus Suttermans (aka Sustermans) was a renowned portraitist who served as the court painter for the Medici family and painted other European nobility as well. In contrast, this rare scene depicts three people who served the Medicis: a duck and chicken seller, a peasant woman, and a household servant. Unlike wealthier sitters, the two elderly women here are seen in all their glorious wrinkles. They’re caught interacting, as if photographed in mid-action. The young Black man on the right is seen reaching into the vegetable basket with his left hand and making a vulgar (for the time) gesture with his right hand, which rests on Cecca’s shoulder. Another version of this painting is owned by the Saint Louis Art Museum.

First Floor, E8

Rembrandt, Portrait of an Old Man (The Old Rabbi) (1665)

In the midst of so much Christian art, this portrait of a rabbi stands out for its subject as much as for its dark palette and loose brushstrokes. Rembrandt lived in the Jewish quarter of Amsterdam, which was also an artists’ quarter, and often used people in the community as models. The rabbi’s expression and interlocking hands, suggesting a contemplative demeanor and world-weariness, are exemplary of Rembrandt’s much-admired ability to capture the psychological essence of his subjects.

First Floor, E7