THREE DAYS later I find myself in eight-foot seas off the coast of Serifos Island, trying not to vomit as I wrap the mainsheet onto the winch of a 55-foot sailboat. The boat's skipper, an unflappable 34-year-old Californian named Max Fancher, comes over to assess my work. "You almost got it," he says diplomatically. "Only you should probably wrap it clockwise instead of counterclockwise, since the winch only goes in one direction."

Nodding at my own mistake—a blatant flub, akin to putting on underwear over the outside of my pants—I unwrap the winch and start over.

In spite of my seasickness and nautical ineptitude, I'm happy to be sailing into the heart of the Cyclades—a stunningly beautiful archipelago of some 30 major islands southeast of the Greek mainland in the Aegean. Indeed, when most people envision the Greek islands,

The atmosphere on board the Assos is fun and relaxed. Most of my boatmates share an insouciant intelligence and a predilection for wearing bikinis. I have a crush on every one of them, despite the fact that most of them have thrown up at least once this afternoon.

the Cyclades are what they see: dramatic cliffs and golden beaches; ridges crowned with blue-domed churches; harbors clustered with whitewashed cubical houses. To glimpse these islands from the seat of a plane or the deck of a commercial ferry is no doubt a thrill, but I've resolved to explore them in the purest sense. Just as the Sahara is best seen by camel and Machu Picchu is ideally approached on foot, I'm wagering that the Cyclades are best experienced from the deck of a sailboat.

The only problem is that I know very little about sailing—which is why I've joined an eight-boat flotilla organized by Berkeley-based OCSC Sailing. Our goal for the next two weeks is to island-hop through the Cyclades to the gorgeous volcanic crescent of Santorini, then loop our way back to Athens—a journey of 300 nautical miles. Some of the 46 sailors in our flotilla are folks who've trained for months on San Francisco Bay specifically for this kind of experience; others, like Gar Duke and Nicole Friend, at the helm of the Dafne, are sharpening their skills in anticipation of buying their own boat and sailing it around the world.

Photographs by Max Kim-Bee