Capri Town, Capri Town
Concierge.com's insider take:
Situated just below the postcard-pretty clock tower, the famous Piazzetta (officially known as Piazza Umberto I) is both the entrance to the island's main town and its open-air living room. No matter what lane you're in, you'll eventually end up at this picturesque square, with its four people-watching bars. Each has its fans, but Bar Tiberio has the most authentically local crowd, and the Piccolo Bar is the most tucked away.
Various routes lead out of the Piazzetta. If you head down the shopping street of Via Vittorio Emanuele and take a left by the celebrated Quisisana hotel, you're doing Capri's most classic passeggiata, which leads via boutique-lined Via Camerelle and luxury-hotel-lined Via Tragara to a belvedere next to Punta Tragara overlooking the Faraglioni rocks—a series of mammoth limestone formations just offshore that are home to a species of blue lizards found nowhere else. From the belvedere, a long, stepped path leads around to the Arco Naturale, a natural rock arch, in around 30 minutes.
Back in the Piazzetta, the steps by the side of the church lead up to an arched lane that is a typical example of Capri's souklike vernacular architecture. The other reason to come here is to eat at Da Gemma, one of the island's most traditional trattorias. Opposite the church, the narrow lanes of Via Longano and Via Le Botteghe soon meet up at the little chapel of San Michele, hopping-off point for the 30-minute slog up to Villa Jovis. Also worth a visit are the Certosa di San Giacomo, a medieval monastery set behind a lemon grove; the Gardens of Augustus, a charming public park laid out on a series of terraces high above the sea; and Marina Piccola, a tiny seaside resort with rows of colorful bathing huts.—Updated by Lee Marshall