10 Ultimate Things to Do in Capri, Italy

Between 1876 and 1899, American historian and archeologist Colonel J.C. MacKowen built Casa Rosa, with its striking Pompeian red exterior and eccentric 15th-century Aragonese tower. Today the villa is home to The Painted Island, a permanent exhibition of artwork depicting Capri from the 19th and 20th centuries by Brancaccio, Carelli, and more recently, Milano landscape artist Carlo Perindani.

You haven’t fully experienced Capri until you’ve explored its rocky shoreline, a veritable Swiss cheese of mysterious grottoes tucked into its myriad inlets and bays. As you’ll learn, the Blue Grotto may be world-famous, but there’s also a Green

Grotto, a Yellow Grotto, a Pink, and a White. Unless you possess fins, the only way to penetrate many of these secret recesses is to book yourself on one of the island’s giro (tour) cruises—they have been an iconic Caprese experience since the 19th century. Be warned: during summer months, is the coast is a log jam of tourist boats and small private yachts.

Built atop a rocky outcropping on the eastern side of the island, Villa Malaparte (meaning House Like Myself), is a wonderful example of Modern Italian architecture. Built in 1938 by Rationalist architect Adalberto Libera, the low-built, red-hued villa is almost an organic extension of the island’s natural landscape. It was commissioned by Italian author Murzio Malaparte, whose novel La Pelle recounts scenes from Naples during World War II. Had Malaparte not been a devoted fascist and received the blessing of Mussolini, construction of the villa would not have been allowed on this exceptionally beautiful and pristine coastline. Villa Malaparte is not open to the public.

Capri’s Via Camarelle is a shopper’s paradise, and the high-end boutiques here are a veritable who’s who of Italy’s most celebrated designers. Browse the latest creations by Fendi, Versace, Gucci, Valentino, Balenciaga, Armanie, or Prada. Take a break at any number of old-school cafes and ice cream parlors like Le Camarelle or Buonocore Gelateria.

Down in the lowest reaches of Monte Truoro is the legendary Grotto di Matermania. The cave is dedicated to Cybele, the mother of gods, who was not a part of the Greek or Roman pantheon, but rather of Eastern origins. Each day at dawn, the rising sun illuminates the cave, leading scholars to believe that this was an important shrine for worshippers of the mysterious cult Mithraism, which celebrated the Indo-Iranian deity Mithras. Little remains of the ancient structure, which the Romans later adapted into an opulent nymphaeum, or small shrine.

A 10-minute walk from the city center, this Le Corbusier-designed hotel is lauded as one of the most beautiful in Capri. Tragara’s Michelin-starred rooftop restaurant, Mammà, is the culinary envy of the island, as are their sumptuous suites with enormous half-moon windows that frame the land and sea of Capri.

Taking its name from the ancient Roman god Jupiter, or Jove, Villa Jovis was most impressive (and well-preserved) of all of Emperor Tiberius’ 12 island residences. An architectural wonder in its day, the villa was constructed on the Rocca di Capri that delineates Capri from the tip of the Sorrentine peninsula, Punta Campanella. The views are breathtaking, and the story of ancient Rome comes alive here when you think of its natural fortifications that proved helpful to alerting Rome of any attacks.

Join local sun worshippers on this charming little slice of beach, which is lined with elegant, (often) air-conditioned cabanas. A small natural promontory, Scoglio delle Sirene (Sirens’ Rock), juts out into the bay and divides the beaches of Pennaulo and Marina di Mulo. The Sirens’ Rock is believed to be the spot where mythical temptresses in Homer’s The Odyssey seduced Odysseus, preventing him from returning home to his wife, Penelope.

Located between the Castiglione and Tuoro hills is one of the true highlights of historic Capri: the palatial complex of Certosa di San Giacomo. Founded between 1371 and 1364, it was given as a gift by Queen Giovanna I of Naples to Count Giacomo Arcucci, a devoutly religious man who lived here until his death. The complex was sacked by pirates in the 16th century and later rebuilt and restored on the back of heavy public taxes. Baroque frescos decorate the church, which also contains the Biblioteca Comunale Popolare Luigi Bladier, a public library and the only free internet spot on Capri. Signs will direct you to the complex’s magnificent monastery gardens where there are benches with exceptional views of the island.

Capri is hiking heaven with idyllic pathways running beside cactus-covered cliffs and whitewashed houses overlooking some of the bluest water on Earth. The Giro dell’ Arco Naturale is a stunning hike that takes you past the Arco Naturale, the Grotta di Matermaia, Villa Malaparte, and I Faraglioni in less than two hours.