As the boat approaches the dusty port of Karavostasi, bare, sun-scoured rocks offer little suggestion of the glory to come. After a steep 3-mile climb, cliff-top Chora comes into view. Its sky-kissing perch out of view of the harbor was no accident, as for centuries the southern Aegean was plagued by marauding pirate raiders. Nowadays, Chora is a cozy huddle of whitewashed houses, flower-filled alleys, and brightly painted woodwork that has been lovingly preserved by the islanders. Five squares, closed to vehicles, host restaurants and cafés shaded by bougainvillea and hibiscus. Some of the buildings are set into the walls of the Venetian fort, or Kastro, built by the Duke of Naxos in the 13th century. A street circles the Kastro and the precipice on which the town stands and is strikingly lined with two-story cube houses that form a wall atop the towering cliff. The glory days of Venice came to an end in 1715, when the ruling Turks sacked Folegandros and sold the captives as slaves. Folegandros joined the Greek state in 1828 and in the mid-20th century the island was used as a place of political exile due to its remoteness.
The spectacularly photogenic Church of Komisis tis Theotkou (or Dormition of the Mother of God) dominates the town and stands on the foundations of the ancient settlement near the top of the cliff. At Easter, an icon from the church passes through every house on the island in a three-day festival. The path that zig-zags its way to the church is quite a climb but the rewards are the enchanting views over the town and the island.