Villa il Castiglione, Capri

Set high on Capri’s cliffs, Villa il Castiglione-often shortened to Il Castiglione and literally “little castle”-combines the look of a medieval stronghold with the comfort of a refined retreat. From its terraces you can see the Faraglioni sea stacks, Marina Piccola Bay, the Gulf of Naples, and the Sorrento Coast-an expansive panorama that few spots on the island match.

Mediterranean gardens and stepped terraces lead to a dramatic pool set right on the cliff edge, frequently noted as one of Capri’s most striking swimming spots. Inside, the villa offers about 1,000 square meters of elegant interiors. The centerpiece is a large living room with antique rugs, a majolica-tiled fireplace, and broad picture windows that make the Faraglioni feel close enough to touch.

There are five bedrooms in total, four of which look directly toward Capri’s coastline and the open sea. The master suite includes a spacious private terrace for quiet downtime, with additional bedrooms completing the sleeping area. Although it’s well placed for reaching the island’s highlights, the property remains surprisingly calm and secluded. Sitting roughly 200–370 meters above sea level, it was recognized as “Europe House of the Year” by The Wall Street Journal in 2013.