If I had to be honest, I would say our trip to Greece was the direct result of an early mid-life crisis. After years of climbing the ranks in the chaotic world of advertising, I was ready to do something meaningful and lasting with my life. So when the agency’s owner asked me to choose 20 people from the staff to let go in an upcoming re-org, I jumped at the chance. After discussing the matter with Marcus, I submitted a list with one name on it: mine. We sold our house, furniture and all, to a bachelor looking for a “pre-loaded” second home. Then we packed our bags and flew to Athens, where we met up with friends who had inspired the trip.

Giddy with newfound freedom, Marcus and I toured the ancient Acropolis, marveled at the Parthenon, explored the Agora, shopped the local market, and pursued a Mediterranean diet. All the while, long forgotten humanities studies came rushing back in vivid detail. Yes, there were crowds, but we hardly saw them through our Hellenic daze so lost in mythology, The Iliad, and The Odyssey were we. Later that evening, en route to our Poseidon-themed hotel, we noticed locals streaming from their homes. This was the first hint at what our skipper later referred to as “Greek Mean Time.” As in many places where the days are hot, Greeks come out at night.

The next morning, we boarded a small plane for Leros, an island in the Aegean archipelago known as the Dodecanese. Although Dodecanese translates as “twelve islands,” there are more than 163 in the arrangement, 26 of which are inhabited. The larger islands, such as Rhodes and Kos, are popular stops for cruise ships. Thanks to the deft designs of our travel planner, we were scheduled to sail mostly among the small wonders of the region. Our itinerary included: Leros, Arki, Patmos, Marathi, Lipsos, Agathonissi, and Kalymnos.

A common theme among the Dodecanese is that they have changed hands repeatedly since ancient times. Each of the battles left scars and each of the occupiers left architectural and cultural influences that have melded into the islands’ lore. On Leros, for example, you can hike to the remains of a temple to Artemis, erected by the Spartans. A medieval castle built by the Knights of St. John, is believed to sit atop an ancient Byzantine fortress. And the town of Lakki, an oft-targeted WWII naval base, surprises many with its Italian Rationalist architecture. The port at Lakki is where we boarded a lithe, Atlantic sailing yacht that was named for an exquisite film star and skippered by an amiable Englishman.

Our first destination was Arki (or Arkoi), home to a population of 50, a herd of goats that roams the hills with their little bells clunk-clunking, and a couple of tavernas, which were shaded by pergolas festooned with bright fuchsia bougainvillea. That evening, we dined on braised goat, lush salads, creamy cheeses, and fresh-from-the-sea calamari. As became our routine, Marcus and I rose early the next morning, ordered coffee at the taverna, and watched weathered fishermen mend their nets. Here, “American” coffee meant freeze-dried instant, so we always opted for Greek coffee – a thick, meaningful espresso that leaves woody grounds in the bottom of your cup. Around noon we set sail for Patmos, where we joined religious pilgrims on tours of the Monastery of St. John the Theologian and the Cave of the Apocalypse. In a study of opposites, a few of us then hiked to a “naturalist” beach, which spurred lively conversation about modesty back home in the land of the free and the brave.

Most evenings we dined as a group on the cool stone patio of a local restaurant or at a long table set on the beach beneath the stars. Each taverna offered its own twist on late summer Aegean cuisine. Everything was made fresh from local ingredients: grilled meat and fish, salads and grape leaf dolmades, tasty souvlaki, flaky spanakopita, hearty moussaka. In each port, we mingled with other sailors from Greece, Turkey, the U.K., Italy, France, Sweden, Germany, and Norway. Away from the large crowds on the “poster” islands, we were free to rent scooters and explore the white-washed towns and surrounding hillsides. To linger in outdoor cafés with expansive sea views. Climb to little white chapels with hand-painted blue domes. Go for a swim or lounge on an ancient beach.

With a seasoned skipper and crew, and only 3 - 5 hours of sailing each day, life was pretty grand. We spent each night in port, drank coffee with the sunrise, then hoisted the anchor and sailed off into the late morning sun. At sea, we took turns furling and unfurling the sails, manning the helm, and lounging on the teak deck. In the afternoon, we’d stop for lunch and a swimming, snorkeling, or cliff diving (!) adventure. At one such stop we swam through an underwater cave to an interior lagoon that was out of this world. At another, the boys took turns free diving to test their dive watch altimeters. At some point, an impromptu cocktail party usually broke out. It was these lazy days that embedded in us a deep and abiding love of full sails, cool white linen shirts, and gin and tonics with lime.

On the island of Marathi, the taverna’s waitress – a black-haired beauty named Tula – brought us fresh fruit and homemade yogurt that put American “Greek” yogurt to shame. Reinvigorated, we spent the day swimming, snorkeling, and exploring the ruins of crusader castles, classical churches, and hidden gun stations. On board that night, sipping boat drinks after a boisterous dinner ashore, we saw a strange glow in the water. Our skipper, a career chemist, launched into the concept of bioluminescence. Gesticulating wildly to bring his explanation to life, he knocked his prescription glasses ‘ka-plunk’ into the water. Thinking they were gone forever, we half-heartedly marked the spot with a buoy and turned in for the night. The next day, he and Marcus dove down and retrieved the wayward spectacles to everyone’s delight. Then we pulled up the anchor and sailed for Leros and a bitter-sweet finale at the popular Savana Bar.

The next morning, coffees in hand, Marcus and I waved a sad goodbye to our yacht as she set sail without us ... then decided to find a hotel and stay on the island a few more days. We had tasted real freedom – the wind in our hair, the feel of the keel slicing through the sea, the casual comfort of ubiquitous tavernas. It’s no small wonder we wanted more.

ENSEMBLE TRAVEL GROUP is an international consortium of travel agencies. This article was written for the organization’s Ensemble Lifestyles magazine.