Known for its limestone cliffs and waterfront villas, this 4-square-mile speck in the Tyrrhenian Sea fully embraces the concept of la dolce vita. (For proof, look to the afternoon crowds stretched out on the rocks and sipping Prosecco at the glamorous La Fontelina beach club.)
A funicular railway whisks visitors from the main port to the boutique-lined streets of Capri town; privacy-seekers keep heading upward by foot or bus to the quieter village of Anacapri. There, stroll through the gardens of the 19th-century Villa San Michele with only ivy-covered statues for company.
Room to Book: No. 2 at J. K. Place Capri for a roomy terrace and dreamlike water views.
Table for Two: Sign up for a cooking lesson at the agriturismo TerraMMare, where you’ll make, and then dine on, traditional island recipes.
Don’t Miss: The nightly passeggiata, when well-heeled Italians glide through the streets at sunset before settling in at a bar on the piazza to watch the action unfold.