Like vagabonds, the seven of us, duffels in tow, loitered leisurely along the bustling quays, tavernas and kafenia of Naoussa harbor on the Greek island of Paros. (Perhaps only in the Mediterranean do “leisurely” and “bustling” not seem contradictory.) We were killing time, on the lookout for Stuart and Monique, neither of whom we’d ever met. They were, respectively, the skipper and the cook for the sailboat we had chartered.

The sailboat should have been easy to find: a 54-foot Jeanneau monohull (as opposed to catamaran), so new it didn’t yet have a name emblazoned on its stern. We apparently would be its very first paying guests. But other than that description of the boat, among the hundreds of others at anchorage in the harbor, we had no firm idea of what we were looking for, much less what exactly to expect during the coming week of island-hopping in the Cyclades.

All of us had some experience sailing, but only two, Dan and Elaine, had ever chartered a sailboat in Greece. My wife, Pat, and I had never even been to Greece, but it was always a dream destination. Originally, I had wanted what’s called a “bareboat charter” — meaning I would be the skipper. Although they politely used other excuses, none of my friends wished to risk their lives serving as my crew.

After prudently deciding on a crewed charter, the next choice had been which of the Greek isles to explore. Each of the island groups offers a different experience, from the olive groves and resorts of the Ionian islands (including Corfu and Odysseus’s Ithaca) to the fine beaches and Ottoman architecture of Rhodes and the other Dodecanese, scattered along the Turkish coast.

The rich mixture of quaint villages, stunning beaches and 5,000 years of history made our choice the Cyclades. Which of the seemingly countless arid islands we would actually visit would be determined by winds and whimsy. There would be no fixed itinerary. What was known was our starting point: the island of Paros, which we reached via a four-hour ferry ride from Athens.

Attesting to its popularity, the Naoussa boat slip on the island of Paros is crowded, as the solitude of the open sea beckons. (Walter Nicklin/FTWP)
When we finally found our chartered sloop-rigged yacht in its slip, there was Monique, an expat American, with bags of provisions in her arms. Besides the requisite wine, beer and olive oil for the next several days, she had all the ingredients for our very first meal on the boat: roasted small tomatoes with garlic and oregano, tossed with tuna and capers and penne pasta. No matter what Poseidon had in store for us, Monique would ensure that we would be well fed with a healthy Mediterranean diet.

Soon Stuart the skipper appeared, with his own duffel from his home base in England, and we prepared to cast off. Those of us with the most sailing experience — Nina, Dan and I — volunteered to serve as his crew. He would turn out to be a solicitous captain — never barking orders but simply suggesting and instructing . I think Pat, always a nervous sailor, was expecting a Captain-Ahab-like authoritarian. “Princess Panics-a-Lot” is the teasing moniker that Stuart would gently bestow upon Pat whenever she would get anxious that, beating to windward, we were heeling too much and might tip over.

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