Sheering out of the sea just off the far end of the Sorrentine peninsula, the island of Capri has long been the most sought-after part of the Bay of Naples. During Roman times Augustus retreated to the island’s gorgeous cliffbound scenery to escape the cares of office; later Tiberius moved the imperial capital here, indulging himself in legendarily debauched antics until his death in 37 AD. After the Romans left, Capri was rather neglected until the early nineteenth century, when the discovery of the Blue Grotto and the island’s remarkable natural landscape coincided nicely with the rise of tourism. The English especially have always flocked here: D.H. Lawrence and George Bernard Shaw were among its more illustrious visitors; Graham Greene and Gracie Fields had houses here; and even Lenin visited for a time after the failure of the 1905 uprising.
Capri tends to get a mixed press these days, the consensus being that while it might have been an attractive place once, it’s been pretty much ruined by the crowds and the prices. And Capri is crowded, to the degree that in July and August, and on all summer weekends, it’s sensible to give it a miss, though the island does still have a unique charm, and it would be hard to find a place with more inspiring views. It is expensive, although prices aren’t really any higher than at other major Italian resorts, and you can find very reasonably priced and attractive accommodation in Anacapri. Alternatively, just visit on a day-trip, which should give you time enough to see the major sights of the island.