Boats among the many hundreds of Greek isles in the Aegean Sea. (Ivan Bastien/Alamy Stock Photo)

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/For The Washington Post)

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.

That night, a Saturday, we anchored in a small bay, quiet and secluded, not far from the busy port of Naoussa but on the same island of Paros. Each couple had a private sleeping berth and head. The gentle rocking of the boat and lapping of seas against the hull brought deep and blissful sleep that — after flights across the Atlantic to Athens and then battling city traffic to get to the Athens port of Piraeus for the ferry — seemed especially well earned.

As the very first rays of Homer’s “rosy-fingered” dawn filtered through the portholes, Monique was already awake, making breakfast. My job was to hoist the anchor. There was a bit of breeze, so Stuart lifted the mainsail and jib to supplement the inboard motor. Dan and Nina’s job was to winch the sails, as Stuart instructed. The rest of the crew — Elaine, Ann, Pat and John — stretched out in the cockpit or on the deck, to feel the wind and marvel at the beauty of the “wine-dark sea.” We were on our way to the sacred, uninhabited island of Delos.

The islands of the Cyclades, meaning “circle,” derive their name from the way they orbit around the figurative sun of Delos — now a UNESCO World Heritage Site and one of Greece’s most important archaeological locations, dating to the Bronze Age. Headless and limbless statues, mosaics picturing dolphins, phallic monuments in homage to Dionysus, a dried-up lake where Apollo is said to have been born . . . . When American civilization collapses, will it leave behind such enchanting and enduring ruins?

That afternoon we sailed to nearby Naxos, the largest of the Cyclades. The cove we anchored in was tiny. With a fishing village as our backdrop, it was the perfect place to take a dip in the crystal-clear waters. Stuart created a swimming platform off the stern, and we all dived in. Afterward, to dry off, you really didn’t need a towel; the hot, arid air was enough. It was then that we decided that, rather than sail to tourist meccas such as Santorini and Mykonos, we’d stick to out-of-the-way beaches and bays. To go where cruise ships don’t go, we realized, was perhaps the biggest advantage of a sailboat charter.

Thus our next stop: an island not even mentioned in the voluminous travel guide to the Greek Isles that I lugged around with me, wild and rocky Donoussa. There’s nothing like a good swim to work up a good appetite, so Monique had lunch waiting when we climbed back on board: chicken stuffed with feta, herbs, lemon, together with small potatoes boiled, then smashed and fried with garlic and rosemary. Did we nap after lunch, lulled to sleep by the gentle rocking of the boat? I don’t remember.

With the sailboat snug in the horseshoe-shaped harbor below, there’s ample time to hike and explore yet another rugged Aegean island. (Walter Nicklin/For The Washington Post)

The endlessly exquisite variations on our Mediterranean theme meant that the hours blended so seamlessly I soon would forget what day of the week it was, not to mention find it difficult now to create a retrospective catalogue of each and every separate experience while sailing among islands with magical names like Amorgos, Koufonisia and Shinoussa. Where were we on our voyage when we went ashore for a strenuous hike up a steep, rocky path to an ancient monastery? And where and when exactly did we encounter that bronzed, totally nude, very much alive — and Greek-god-like! — couple on an otherwise deserted beach?

But with the crystal clarity of the Greek seas and sky, I do remember this: my birthday, which happened to fall midway in our voyage. For dinner onboard, Monique prepared salmon with herbed crust, fresh tomatoes with mozzarella and basil, followed by a birthday cake complete with candles. Afterward we motored to shore in the inflatable dinghy to find a terraced overlook as the sun set over our sailboat at anchor down below, so small it looked like a child’s toy. Enhancing the view were after-dinner toasts with the Greek spirit ouzo — the boiled residue of grape skins from wine-pressing. I don’t think I’ve ever had a better birthday.

Nicklin is a writer based in Virginia and Maine. His website is Find him on Twitter: @RoadTripRedux.

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For a week's charter, our cost was roughly $10,000, which covered the skipper, the cook, food, cleaning, docking fees, as well as the rental of the boat itself. Submit a query at to book. A security deposit of roughly $3,000 was also required. We bought an insurance policy for about $200 to cover any dings, scratches or other possible damage to the boat.