The splendid Isle of Capri rises from the Tyrrhenian Sea and greets the Sorrentine Peninsula. Having become famous with the discovery of its Blue Grotto or Grotta Azzurra in 1826, Capri is a place of legend that continues to be a main destination for travelers, stars and intellectuals. 

Among the first to be captivated by it was the Roman Emperor Tiberius, who went into self-imposed exile in his own magnificent Villa Iovis, known as “Tiberius’s Palace.” One can reach it via a 45-minute walk from the tiny Church of San Michele.

To the right of its ruins, one can admire the so-called Salto di Tiberio or “Tiberian Drop:” it is recounted that from this viewpoint the Emperor made his enemies “walk the plank," as it were. The Emperor Augustus was also a regular on the Island and in fact, Capri was already highly-favored by the Romans, so much so that this magnificent place became the location of 12 Imperial villas. 

In the 1950s, Capri was the official home to la dolce vita, especially during the summer season, when the jet-set and world-famous personalities populated it. Above all, it was Jacqueline Kennedy who stamped Capri with her own style: although rope sandals already were the epitome of Capri fashion, Jackie O took things a step further and instead went barefoot! This gorgeous paradise, besides being the stomping ground for illustrious personages, is internationally-known for its natural beauties, its millenary history, temperate climate, and luminous landscapes. 

A sea of cobalt blue hosts grotto after grotto – 65 in total – and sea-stacks or faraglioni. Of the latter, the three best-known are “Stella” at 109 m (358 ft) high, “Faraglione di mezzo” (81 m or 266 ft), and “Scopolo” at 104 m (341 ft).

Be sure not to miss a visit by motor boat or smaller watercraft to the Blue Grotto; 25 meters wide, its name derives from the marvelous color of the seabeds reflecting inside the grotto. 

Gaze at the panorama along the ample harbor of Marina Grande, both the port and departure point for the Island’s funicular that, in 12 minutes, makes its way up to Capri’s top.
Small houses made of tufo lava stone, roof terraces, arches, trellises, winding and climbing streets that pop out on Piazza Umberto I; the “Piazzetta,” the city’s open-air living room surrounded by cafes and perfect for enjoying the amazing view on Marina Grande; the Church of Santo Stefano (reconstructed in 1600 and fusing together Baroque forms with cupolas that seemingly create arabesques); and Palazzo Cerio, at one point the Castle of Giovanna I d’Angiò (Joan I of Naples) and today the seat dedicated to the history of the Island - these are the things that personify Capri.

Afterward, take the staircase to arrive at level ground with the Chapel of Santa Maria del Soccorso: the sight of the Gulfs of Naples and Salerno is, in a word, breathtaking. The panoramic view of Tragara also offers a vision that enchants, comprising the sea-stacks and Marina Piccola. 
Not to be left out, and just as spectacular, is the Natural Arch, the remains of an enormous cavity standing out on the coastline. 
Anacapri is the Island’s second center, immersed in olive trees and vineyards. While on Capri, make the effort to visit Piazza San Nicola; the Church of San Michele, which features a beautiful majolica floor; and Villa San Michele, with an arbored garden that entices visitors to stop and relax in its tranquility. 

Other must-sees include: Capo Massullo, in a spectacular panoramic position, is the base of the Pompeiian Red house belonging to writer Curzio Malaparte. This rather particular work of architecture represents a masterpiece of Italian rationalism. 

Finally, nature lovers would do well to ascend Monte Solare (589 m or 1,932 ft), either on foot or via the chair lift; those who do so will be rewarded, for it is where they can see the ruins of Fortino di Bruto, a castle from the early 1800s.

Be sure to see: The Islands of Naples Bay: Procida, Capri and Ischia