TWO DAYS OUT OF SIFNOS, the rain clears and we sail into the caldera of Santorini under brilliant blue skies. Often associated with the lost city of Atlantis, this caldera dates back to around 1500 b.c., when one of the biggest volcanic eruptions in recorded history collapsed the middle of the island and sent deadly tidal waves surging out across the eastern Mediterranean. More than 3,500 years later, the dramatic, red-veined cliffs that rim the caldera are studded with elegant churches, flagstone paths, and pastel-hued houses. It's a singularly gorgeous sight, and we trim in our sails and drift around the 32-square-mile caldera to take it all in.

Later, when my boatmates and I dinghy in to the Santorini shore, we discover an island snarled with rental-car traffic jams, high-tension power lines, and billboards for places like Señor Zorba's Mexican Restaurant. After the sleepy anonymity we enjoyed on Sifnos, this comes as a letdown.

We make our way to the clifftop village of Oia, which proves more authentic, with its twisting alleyways, cave houses, and grand Orthodox churches, though visitors from places like Houston, Helsinki, and Hong Kong easily outnumber the 500 or so locals. The time-honored tradition here is to photograph the sunset as it glitters over the waters of the caldera below, and the crew of the Assos is not to be left out. Brandishing our digital cameras, we position ourselves among hundreds of fellow tourists at cliffside, each of us trying to catch the perfect angle of sunlight on the whitewashed mansions and church domes—without getting one another's arms and heads and cameras in the frame.

Of course, Santorini isn't the goal of our flotilla as much as a pivot point. After two nights anchored off the volcanic crescent, we begin our journey back to Athens.

As we follow the winds home, each new island yields humble discoveries. On Sikinos, I dine on wild rabbit and hike at night under the stars; in the marble-studded mountains of Naxos, I talk politics and drink Nescafé with Greek shepherds; on Paros, I eat ice cream along the harbor while a film crew shoots scenes for a Greek soap opera. Not the stuff of Odysseus, perhaps, but I find charm in the buzz of each little adventure.

On our final day at sea—the 39-mile leg from Kea to Marina Alimos, outside Athens—a pod of dolphins begins to flirt off our port bow. We fire up the engine and weave along with the gray creatures for the good part of an hour before running out of fuel. In an instant, the dolphins are gone and the Assos is left bobbing off the Greek coast.

We have only a hint of wind for our sails—and the port is still more than ten miles away—so Captain Max has us haul out a colorful spinnaker. With two weeks of experience behind us, we rig the downwind sail with cheerful efficiency.

For a moment, we roll with the waves as the spinnaker hangs limp at the bow. Then a slight breeze billows the sail, and we witness a phenomenon as elemental and bewitching as a bolt of lightning or a spark of fire: Wind and boat connect, lines go tight, and we surge forward.

As we slowly float toward Athens, I again think back to Pavlo the Sailor. Nearly 100 years ago, the Greek poet Constantine Cavafy also used the example of Odysseus to downplay the importance of one's final destination. To paraphrase his poem "Ithaca": Don't expect Ithaca to give you riches. It has already given you this journey.