What to Do in Capri

Capri can be a bewildering place for first-time visitors. In summer, throngs of day-trippers arrive by ferry at the Marina Grande and flood Capri town, getting lost in the maze of crooked lanes that were once designed to confound marauding pirates.

The most famous lookouts over the Fariglioni, the trio of giant rock spires jutting out of the Mediterranean, can feel as crowded as Shanghai train station. If at all possible, stay overnight on the island. Even better, remain several days. The extra time allows you to explore the remoter recesses of the island, revealing why Capri has bewitched writers throughout history, from the ancient Roman poet Statius to the Chilean Pablo Neruda.

THE CELEBRITY HUB
After 5 p.m., when the crowds leave, even Capri town becomes blissfully quiet, and you can wander the cobbled lanes flanked by elaborate iron fences and glazed tiles, feeling as if you’re in a glamorous Italian film shoot, circa 1950. Head for the Piazzetta, or small plaza, settle into the Bar Tiberio for a glass of prosecco and watch the evening unfold. The Piazzetta is possibly Italy’s most beloved public stage, where silver-haired waiters in cream tuxedos serve suntanned celebrities on hiatus from their modeling jobs or TV series. Afterward, repair for dinner to Da Gemma, a historic restaurant once frequented by the British novelist Graham Greene, a resident for long stretches of the 1950s and ’60s (according to Shirley Hazard in Greene in Capri, he favored the corner table). The arched entrance, carved into an ancient rampart, is covered with faded photographs of Shirley MacLaine, Sophia Loren and a mysterious blonde woman from the postwar era nicknamed “Million-lira,” because, a maitre d’ once told me imperiously, “she was the first to charge a million lira a night!”

Greene’s novels, as well as rare reprint editions of the works of the many writers, artists and photographers who have made Capri their home over the centuries, can be found at the bookstore La Conchiglia Libri e Arte, at 12 via le Botteghe. Owned by Ausilia and Riccardo Esposito, it’s also the best place to find out about the latest cultural events on the island.

THE HEIGHTS OF PLEASURE
From the main town, take one of the white Mercedes convertible taxis ($20) up vertiginous hairpin bends to the revered Hotel Caesar Augustus in the village of Anacapri (“Upper Capri”). For the past six decades, this has been the most sought-after place to stay on the island, partly because of it is perched on the knife edge of a 1,000-foot cliff. Today, the terrace still offers one of the best views in the Mediterranean—a jaw-dropping panorama across the Bay of Naples to Vesuvius, the volcano that buried Pompeii and Herculaneum in A.D. 79. A gleaming statue of Augustus, the first Roman Emperor, gestures grandly toward the vista. If you can’t stay, be sure to have an aperitivo at dusk; the sun sinking into the sparkling sea bathes the whole Neapolitan coast in a dream-like, golden glow.

As it hovers aloof above the rest of the island, Anacapri still proceeds at a 19th-century pace. Schoolchildren in white uniforms play soccer in the cobbled streets, while elderly residents tend their backyard lemon groves. On the piazza, the Church of Santa Sofia has a magnificent ceramic floor depicting the Garden of Eden, and you can peer through a grille at Graham Greene’s former home, the villa Il Rosaio, now a private residence whose entrance is framed by peach-colored roses.

The Villa San Michele, an art-filled refuge created by Swedish physician, author and amateur archaeologist Axel Munthe, is Anacapri’s most popular attraction. Few visitors realize that the villa’s current owner, the Swedish Culture Institute, hosts tours every Thursday afternoon to a unique nature preserve. Visitors climb a steep trail to the spectacular ruins of Castle Barbarossa, a 10th-century fortress on Monte Solaro that now operates as the Capri Bird Observatory. Muthe was an outspoken animal lover, and he bought the mountain above his home to protect its birdlife. Ornithologists today using a system of nets capture and study birds migrating from Africa to Europe – a simple technique that was pioneered by peasants centuries ago so that Caprese quails could end up on European dinner tables. Today, up in the windswept belfry of the castle, local naturalists in pince-nez glasses tag golden orioles, then cast them back to the wind.

INTO THE WILD 
Thanks to Capri’s tortuous topography, three-quarters of the island is virtual wilderness, some of it so precarious that a few hikers disappear off the cliffs every year. But those with the leisure and energy to follow solitary backcountry trails can discover a landscape that has barely evolved since the ancient Romans holidayed here.

Many paths begin in town, right under everybody’s noses. The Belvedere de Tragara is the most popular lookout over Capri’s natural phenomenon, the Faraglioni. (“Those famous Gothic cathedrals,” said the irrepressible Italian futurist poet Marinetti of the stone fingers, “with their spires and their ramparts rising fiercely out of the sea.”) In one corner of the lookout, overlooked by most visitors, there is a narrow path called the Via Pizzolungo, which was carved in pagan times. Ten minutes into the pine forest, a stairway plunges down to sea level, where a café – Da Luigi – sits at the very base of the stone pillars, like the Clashing Rocks in Jason and the Argonauts. While the water laps at your feet, the owners will show off photographs of the winter storm of 1986, when Poseidon-size waves tried to pull their little café into the sea.

In the northwest of the island, a steep path from the Villa Lysis provides the back route to the emperor Tiberius’ palace, the Villa Jovis (Villa of Jupiter). Ascending the mountainside covered in wildflowers of purple and gold, one can easily imagine this to be the same path a young islander once climbed, according to the ancient author Seutonius, to offer Tiberius a mullet. The reclusive emperor was so enraged that an intruder had penetrated his lair that he ordered his guards to rub the fish in the peasant’s face. Apparently, when the enterprising youth joked (rather wittily) that it was lucky he had not brought Tiberius a lobster, the humorless emperor had his face torn to shreds with crustaceans. At the summit lie the ruins of the notorious palace, including the sheer Salto Tiberio from which the emperor is said to have thrown unlucky senators to their deaths. The excavations give only a hint of the precinct’s former glory, but the view is unsurpassed. Say what you like about Tiberius, he had a fine eye for real estate.

For me, the ultimate Capri hike is the Sentiero dei Fortini, the Trail of the Forts, on the forgotten west coast of the island. It starts amongst garden terraces but soon leads to a series of wild headlands crowned by a string of medieval towers. On this remote, cactus-strewn shoreline, the sea is a dazzling shade of green. Lizards are poised motionlessly along the trail like nature’s gargoyles. At irregular intervals, carved stone steps lead down to the water. There are no sand beaches on the route, just dark rocks from which you can leap into the crystalline water. Gazing up at the brooding cliff faces, you can imagine history’s many visitors to Capri—the parade of ancient aristocrats, rebellious Victorians and troubled writers—swimming in the same spot. As the Roman poet Statius wrote of Capri in the second century A.D., “Peace untroubled reigns there, and life is leisurely and calm, with quiet undisturbed and sleep unbroken.”

Tony Perrottet’s forthcoming book, The Sinner’s Grand Tour: A Journey Through the Historical Underbelly of Europe, recounts a trip from London to Capri.

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Tony Perrottet is a contributing writer for Smithsonian magazine, a regular contributor to the New York Times and WSJ Magazine, and the author of six books including ¡Cuba Libre!: Che, Fidel and the Improbable Revolution that Changed World History,The Naked Olympics: The True Story of the Ancient Games and Napoleon's Privates: 2500 Years of History Unzipped. Follow him on Instagram @TonyPerrottet.