Capri

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, and a highlight of any Southern Italy tour. In Roman times, Augustus escaped here to enjoy the island’s dramatic cliffs and sea views; later, Tiberius moved the imperial capital to Capri, indulging in famously debauched antics until he died in 37 AD.

After the Romans left, the island faded into obscurity until the early 19th century, when the discovery of the Blue Grotto and Capri’s striking natural beauty sparked a new wave of tourism. The English, in particular, were captivated: D.H. Lawrence and George Bernard Shaw were among its more famous visitors, while Graham Greene and Gracie Fields owned homes here. Even Lenin stayed for a time after the failed 1905 uprising.

Capri gets mixed reviews these days. Some say it was once a beautiful escape, now overrun by crowds and sky-high prices. And they’re not wrong. Come July, August, or any summer weekend, it’s packed to the point where you might want to skip it altogether.

But if your Italy trip includes Capri, time it right. Outside peak season, the island still has something special. Its dramatic cliffs, narrow lanes, and sweeping sea views haven’t lost their power to impress; you just have to share them with fewer people.

Villa San Michele

It’s a short walk from Piazza della Vittoria, past a line of souvenir stalls, to Villa San Michele, a light-filled house with fragrant gardens that remains one of Capri’s highlights. Built by Axel Munthe, a 19th-century Swedish writer and physician to European aristocracy, the villa is filled with his personal furnishings, Roman artefacts, and columns salvaged from a ruined villa on the site.

As part of a Rome and the Amalfi Coast tour, this stop offers a peaceful contrast to the island’s busier spots. Don’t miss the small natural history exhibit in the garden, which offers insight into the local flora and fauna.