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Few places in the Mediterranean carry the weight of myth quite like Capri. Rising from the Tyrrhenian Sea off the tip of the Sorrentine Peninsula, this limestone island has drawn emperors, poets, and painters for two millennia. Tiberius ruled the Roman Empire from here for the last decade of his life, retreating to Villa Jovis on the island's eastern heights, and the ruins still stand above a sheer drop to the sea. That combination of natural drama and layered history gives Capri a quality that outlasts any season.

The island divides itself between two settlements. Capri town, perched on a saddle between the island's two peaks, is a place of narrow whitewashed lanes, bougainvillea spilling over garden walls, and the famous Piazzetta, officially the Piazza Umberto I, which functions as an open-air drawing room from morning coffee to late evening. Anacapri sits higher on Monte Solaro and has a quieter, more residential character; the chairlift to the summit rewards the ascent with views that take in the entire Gulf of Naples, Vesuvius, and on clear days the distant outline of the Amalfi Coast.