COMPARED WITH THE MARQUEE islands of the Cyclades—Santorini, Ios, Mykonos—Sifnos doesn't have much of a reputation. According to Herodotus, the gold and silver mines on this 30-square-mile island made it the richest in the Aegean in the sixth century b.c. Two hundred years later, with its wealth exhausted, it collapsed into insignificance. Since then, Sifnos (pop. 2,500) has existed as a nondescript outpost, known more for its poets and pottery than politics or geography.

Despite the island's lack of distinction, however, the Assos (as my boatmates and I have taken to calling one another) immediately fall in love with Sifnos. The tourist crowds have left with high season, and we have the island mostly to ourselves. Renting motorcycles, we cruise up intricately terraced valleys to the central plateau,

The more time I spend aboard the Assos, the more I appreciate the way sailing connects me to the rhythms of the weather and the water. Away from land, life is less of an abstraction, and the sea gradually reveals itself as an intricate and powerful wilderness.

where the houses of Apollonia lie scattered like big white dice among blue-domed churches and olive groves. We wander out to the far coast and swim off empty beaches under ridges dotted with almond trees and clumps of wild juniper. We explore the mazelike alleyways in the hilltop fortress of Kastro, with its bright-pink bougainvillea creeping over shuttered windows and stray cats blinking in the sunlight. In the evening, we sit outside at wooden restaurant tables and dine on tzatziki, olives, stuffed peppers, lamb, and local white wine. After dark, we hike up to the empty monasteries overlooking the harbor, where we listen to the wind and the tinkling of goat bells. One day on Sifnos stretches into two, two days stretch into three.

Photographs by Max Kim-Bee