Crystal-clear waters, family-run tavernas and an ocean of Greek mythology: Our writer boards an intimate sailboat for a voyage far from the crowds in the Aegan Sea.
By Hester Underhill
Over there is Delos, birthplace of the goddess Artemis,” says Fotis Angelopoulos, one hand on the steering wheel of an Ocean Star 56 sailing yacht and the other motioning toward a distant landmass rising dramatically from the deep-blue waters of the Aegean. “And that’s Syros,” he says, pointing across the cloudless horizon to another island. “It’s where the god Hermes was born.”
We’re speeding across the water toward Naxos, our sails billowing in the wind as an unseasonably warm October sun beats down on the deck. Around us lie scattered Greece’s Cycladic islands, each with its own striking landscapes steeped in myth. Fotis, a skipper for Intrepid Travel, has been touring visitors across this archipelago for the last five seasons. Ours is an eight-day trip, with Fortis, a charismatic figure with a wide smile and tousled curls that have been gently bleached by the Greek sun, ferrying our group of 11 between Mykonos and Santorini. The islands we visit along the way, he tells us, could vary depending on the weather. “Here in the Cyclades, there is a strong north wind we call the Meltemi,” he says, cranking in a thick red rope to tighten the white expense of outstretched sail. “It means the waters can get quite choppy, particularly in July and August. So, you can only tell a few days in advance which islands will be safe and easy to reach.” In Greek mythology, the Meltemi was controlled by Boreas, the god of the North Wind. Known for his temperamental nature, Boreas’ capricious moods would often result in turbulent weather and rough seas. Luckily for us, Boreas seems to be in good spirits during our trip, as a calm but persistent breeze propels us between islands.
The Cyclades is a group of more than 200 islands and islets, only 33 of which are inhabited. The archipelago is named after the Greek word kyklos (circle), as they form a loop around the sacred island of Delos, the birthplace of Apollo, god of the sun, and his twin sister Artemis, goddess of the hunt. Characterized by whitewashed houses, winding streets and blue-domed churches, the Cyclades are famous for their crystal-clear waters, rugged landscapes and postcard-perfect beaches. Among the most iconic are Mykonos’ Paradise Beach, known for its golden sands and vibrant party scene, and Santorini’s Red Beach, with its crimson-colored cliffs. But it’s not just a haven for sunseekers, the Cyclades are rich in history, dotted with important archeological sites that connect visitors to the ancient civilisations that inhabited them for millennia.
In recent years, however, certain Cycladic islands, namely Santorini and Myokonos, have experienced overcrowding as tourism numbers surge during the peak summer months. In search of tranquility, some visitors are traveling in the shoulder seasons or venturing farther into the Cyclades to discover its lesser-known isles, I’m doing both. On Intrepid’s Sail Greece: Mykonos to Santorini itinerary, we moor for up to two nights on each island we visit, rocked to sleep in our snug cabins by gently lapping waters. On travel days, we set out early (after the breakfast of creamy Greek yogurt and honey), nestling on the padded benches that line the deck and gazing out at the glittering waters and craggy coastlines. When the wind dies down, we spread out across the boat’s wide bow and lazily thumb through paperbacks or take long, sun-soaked naps. We drop anchor in hard-to-reach bays, make picturesque pit stops in small coastal villages and easily nip between remote islets. And with Fotis as our guide, we have our very own insider on hand, an expert in the Cyclades’ remote beaches, off-the-beaten-track tavernas and best spots to catch the dazzling Aegean sunsets.
From Mykonos, it takes us three hours to cross the water Naxos, the largest of the Cycladic islands. Along the way, we’re joined by dolphins, who dart close to the boat. “I’m still trying to figure out when and why they approach,” says Fotis. “I think it’s about energy. If the boat has a positive energy, you’re more likely to spot them.” Fotis doesn’t come from a seafaring family, and he only stepped on a boat for the first time when he was 25. After hearing about an acquaintance’s sailing holidays, he was inspired to learn himself, and he took to it immediately. He completed training in his hometown of Patras, eventually packing up his life to move to Lefkada, an island in Greece’s Ionian Sea.
Fotis spent years proving himself as a deckhand, all while juggling other jobs, before finally graduating to his own vessel. Now, he’s part of a tight-knit community of skippers in the Cyclades. Every port we arrive in, he’s greeted with warm, familial embraces and enthusiastic waves from his fellow sailors. “Sailing is a way to wake up,” he says. “All this connection with nature and the waves, it makes me feel alive.”
Another of Fotis’ passions is Greek cuisine (one of his most cherished possessions is a collection of 15 recipes he asked his grandmother to transcribe before she passed away). Upon arrival at each island, Fotis provides an extensive rundown of where to eat, and which restaurant has the finest wine list, the crispiest fried anchovies or the most succulent oxtail stew. In Naxos, his top recommendation is Axiotissa, an idyllic taverna nestled in a large olive grove. The island is known for its cheeses, and we tuck into generous plates of arseniko, a rich variety made using goat and sheep’s milk, and salty graviera naxou. This is followed by a hearty portion of lamb, slow-baked with local herbs and served with a mound of crisp roast potatoes. We wash it all down with a carafe of semisweet red wine. Believed by some to be the birthplace of Dionysos, god of winemaking and fertility, Naxos regards wine as an important part of its ancient culture, and the island’s tradition of merrymaking is fiercely upheld with a hedonistic carnival that takes place in honor of Dionysus every year before the start of Lent.
From Naxos, we press on to the neighboring Ano Koufonisi, one of the two pint-size islands of Koufonisia, renowned for its clear waters and home to fewer than 400 year-round residents. An enticing expanse of turquoise surrounds the boat when we stop for a swim in the crescent-shaped bay of Paralia Pori. We leap from the deck, equipped with snorkel masks to better admire the small fish that dart around our toes. The next day, we reach the island of Amorgos and drop anchor in the bay of Liveros. It’s the site of the shipwreck of the Olympia, which sank here in 1980, and its vast, rusted form rises like a ghost from the shallows.
We sail along the island’s coast, reaching the port town of Katapola in time for lunch. As usual, Fotis has a suggestion for our midday meal. “Prekas is a very old a nd precious place,” he says, mentioning toward an unassuming seafront kafeneio (café). “Mrs. Zoe is the cook. She prepares two or three special dishes every day, so just go in there and ask what’s on the menu for today.” Prekas opened its doors in the 1960s, and its interiors remain frozen in time: The blue-painted walls are lined with maritime memorabilia and the floors are covered in a mosaic of patterned tiles. Mrs. Zoe is hunched over her pots and pans in the kitchen, and her thickly mustached husband comes over to take our order. The specials for the day, he informs us, are gemista (rice- and herb-stuffed to matoes) and moussaka, which we dutifully order alongside a serving of rich, buttery fava (yellow split-pea dip) and crispy saganaki (pan-fried cheese).
Pleasantly stuffed, we make our way up to the island’s old town, wandering its narrow warren of bougainvillea-strewn alleys before heading inland. The road twists its way across a mountainous terrain that rises and falls before spilling out into the shimmering waters of the Aegean. Our destination is the Holy Monastery of the Virgin Mary Hozoviotissa, a whitewashed structure dating to the 11th century that clings uncannily to stone cliffs nearly 1,000 feet above the sea. After scaling the 350-step stone pathway, we step inside the richly decorated, candle-lit chapel. On our way out, a monk dressed in long black robes offers us a small glass of psimeni raki, a traditional spirit flavored with honey, cinnamon and cloves that’s been produced on Amorgos since antiquity.
This reverence for time-honored rituals, and the enduring presence of Greek mythology, make the Cyclades feel like a place apart. Sailing among its quieter islands is like an odyssey into a past and present so deeply intertwined, it’s easy to lose all sense of time. The only things dictating the days are the gentle rythmes of the sea and the technicolor rise and setting of the sun, an experience so soothing that it lingers long after we disembark in Santorini and say farewell to Fotis.