All the Caravaggios You Have to See in Rome

1. Sick Bacchus at the Galleria Borghese

We begin at the Galleria Borghese, home to a painting that is essential to understanding Caravaggio’s early years in Rome: Sick Bacchus. Around 1592, a young Lombard in his early 20s arrives in Rome, penniless and unknown. He gets by working in the workshop of the Cavalier d’Arpino, painting flowers and fruit to order. It does not last long: he falls ill and ends up in the hospital of Santa Maria della Consolazione.

This Bacchus comes from that time, with its sallow skin and pale lips, a crooked wreath of leaves and grapes nobody feels like eating anymore. It is believed to be a self-portrait: a god turned into a feverish boy. It is a curious choice for someone who has spent weeks in bed. Perhaps Caravaggio saw himself in the god of wine and festivity, of drunkenness, madness, and disorder, exactly what would end up defining his own life.

2. Judith Beheading Holofernes at Palazzo Barberini

We cross the city to the Palazzo Barberini, home of the Galleria Nazionale d’Arte Antica. The boy who got by painting fruit has found a protector. His name is Francesco Maria del Monte; he is a cardinal, and he is passionate about music, science, and painting. He takes Caravaggio into his palace and opens the doors to the Rome of collectors, bankers, and prelates with money and a taste for showing it off.

Such is the case of Ottavio Costa, a Genoese banker who would become one of Caravaggio’s greatest collectors and who commissioned the painting we have come to see, Judith Beheading Holofernes. Caravaggio turns this biblical episode into a scene so bloody and realistic that it shocked the first visitors who came to see it. Holofernes, still alive, screams in agony as Judith beheads him. Caravaggio’s mastery of light and chiaroscuro turns the scene into a kind of photograph that captures the exact instant. His version would go on to inspire the ones Artemisia Gentileschi painted later.

3. Contarelli Chapel at San Luigi dei Francesi

The next stop is a few steps from Piazza Navona, in the church of San Luigi dei Francesi. Head to the Contarelli Chapel at the end of the left aisle, and bring some coins to switch on the lights. In 1599, with the support of Cardinal Francesco Maria del Monte, Caravaggio was commissioned to paint three large canvases for the chapel, his first major public commission.

The chapel is dedicated to Saint Matthew and holds three paintings from his story. The one that deserves our attention is The Calling of Saint Matthew. Christ enters a dark room where men sit around a table counting money, and points at Matthew. Look closely at his hand: doesn’t it remind you of the hand in Michelangelo’s Creation of Adam? The tax collectors wear the clothes of Caravaggio’s own time, and the room could easily be a Roman tavern. A sharp beam of light follows the direction of Christ’s gesture, turning an ordinary scene into a moment of divine revelation. And which one is Matthew? The bearded man pointing at himself, or the younger man still absorbed in the coins? Caravaggio leaves the answer open.

It was an immediate success, and the unknown boy of the Galleria Borghese was now one of the most talked-about painters in Rome.

4. The Crucifixion of Saint Peter at Santa Maria del Popolo

Our next stop is Santa Maria del Popolo, on the edge of the piazza of the same name. After the first Contarelli canvases, Caravaggio was in demand. In the Cerasi Chapel, to the left of the high altar, two paintings by Caravaggio face each other: The Conversion of Saint Paul and The Crucifixion of Saint Peter. Look at the second one.

There is no glory here. Three men struggle to raise the cross with the elderly apostle upside down because, according to tradition, Peter did not consider himself worthy of dying like Christ. We cannot see the executioners’ faces, only their backs, their bare feet, and the effort. The background almost disappears into darkness, while the light picks out the bodies and the cross. The scene is not particularly bloody, but pain is everywhere.

By now Caravaggio was the painter everyone wanted. He was also a man who could not stay out of trouble, and Rome was beginning to notice.

5. The Entombment of Christ at the Vatican Museums

Inside the Vatican Museums, in the Pinacoteca, hangs the painting that many consider the summit of Caravaggio’s Roman years: The Entombment of Christ. Nothing in this painting is shouted. A group of mourners lowers Christ’s body onto a stone slab, and the whole scene seems to slide downwards: from the old man holding his legs to the lifeless hand that almost touches the stone. Look at that hand. Look also at the faces of the Virgin, Mary Magdalene, and the other women, grieving with a restraint that is far harder to paint than any scream. The composition echoes Michelangelo’s Pietà, which you can see a short walk away in St. Peter’s.

This is Caravaggio at the height of his powers. Here there is no scandal, no rejected version, no one raising a fist. Almost two centuries later, Napoleon’s troops seemed to agree: they carried the painting off to Paris, and it came back to Rome only after his fall. For a moment, the painter of the moment was simply the best painter in Rome. But once you reach the top, there is nowhere to go but down.

6. Madonna di Loreto at Sant’Agostino

Let’s continue along our path. We head to Sant’Agostino, where the Caravaggio waiting inside is a very different one. In the first chapel on the left hangs the Madonna di Loreto, also known as the Madonna dei Pellegrini.

This Virgin is no queen. She is a woman standing barefoot in a doorway, holding a child, while two pilgrims kneel at her feet. Look at them: their backs are bent, their clothes are worn, and the soles of their feet, filthy, are the first thing you see. When the painting was unveiled, it caused an uproar. It did not help that popular rumor held the Virgin was modeled on a well-known Roman courtesan.

By now Caravaggio’s life was beginning to look like his paintings: dark, violent and dramatic. This would be his last major public commission in Rome. In May 1606, after a quarrel in the Campo Marzio, he killed a man named Ranuccio Tomassoni. With a death sentence hanging over him, Caravaggio left Rome within days.

7. David with the Head of Goliath at the Galleria Borghese

We end where we began, in the Galleria Borghese. In the same room as Sick Bacchus hangs David with the Head of Goliath. Caravaggio painted it in exile, around, after years on the run through Naples, Malta and Sicily. He sent it to Cardinal Scipione Borghese, the pope’s nephew and one of the most powerful men in Rome, hoping it would buy him a pardon.

The painting is both a confession and a plea. Caravaggio seems to have painted himself twice: as a young man and as an old one. David is a street kid, wild and reckless. Goliath is a battered man, almost destroyed, undone by his younger self. And yet David does not look triumphant. He gazes at the severed head with sadness, and something like pity. Years of hard living and run-ins with the law have worn the painter down. It’s hard to believe the two faces belong to the same man. The boy who once lay feverish in a hospital bed had become a man offering his own head.

We have seen Caravaggio’s whole Roman life: the penniless boy, the cardinal’s protégé, the painter of the moment, the man who could not stay out of trouble. He died in July 1610 and never found out whether he had been forgiven. His paintings, though, are still here-in churches, palaces and museums across the city, waiting for anyone willing to go looking for him. Are there any other Caravaggio masterpieces in Rome that you think are an absolute must-see?