Explore Santorini: Experience the Joy of Sailing the Caldera on Your Adventure

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By Car Brand Experts


Before my toddler started seeing Dr. Finkleman, I had little knowledge about Santorini. While he was a fantastic pediatrician passionate about his work, his conversations consistently revolved around Santorini—mainly its striking blues, both in the sea and the sky. Through Dr. Finkleman, I discovered snippets of its intriguing history, or rather, its mysteries.

It turns out Santorini might have been the site of the fabled lost city of Atlantis, which Plato referenced in his writings, claiming it vanished 9,000 years ago. However, many experts believe that Plato may have mistakenly added an extra zero, suggesting that the correction to 900 years ago aligns with a volcanic eruption that shaped the island’s dramatic crater and cliffs.

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Our catamaran served as a temporary home while exploring Santorini’s caldera/Shutterstock

Normally, I’m not attracted to volcanoes as much as I am to Caribbean beaches or Parisian cafés, and swimming in a volcanic crater wasn’t on my list of things to do. However, my love for adventure and storytelling drew me in. While reviewing excursion options for Windstar’s “Treasures of the Greek Isles” cruise, the “Sailing the Caldera” tour piqued my interest. The description—immersing in green sulfur waters and enjoying a Greek lunch on board—sounded enticing. The mysterious tales of Atlantis made me think that perhaps more stories were waiting to surface from the caldera’s depths.

On a June morning, I joined a small group of fellow adventurers aboard a catamaran named the Odyssey (of course!). As we set sail, our delightful guide, Vaso, a young Greek woman, explained what a caldera is. Essentially, it is the crater of an extinct, or at least dormant, volcano that has filled with water—an important distinction. We recalled our recent visit to Italy, where we learned about a caldera in the Bay of Naples called Campi Flegrei. Scientists reported that if it were to erupt, it could produce enough magma to fill 80 million Olympic-size swimming pools, and the area has been in the news due to recent seismic activity, making locals nervous and prompting tourists to cancel their reservations.

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Exploring the enchanting caldera of Santorini during our Wind Spirit cruise/Shutterstock

Returning to Santorini, I learned that the caldera formed 3,600 years ago in 1600 B.C. when the volcano at the heart of a massive island erupted, effectively obliterating the Minoan civilization. The Minoans had arrived at Santorini from Crete around 3000 B.C. but disappeared after the eruption. Vaso captivated us with tales of the ancient site of Akrotiri, which remains an archaeological enigma, as no human remains have been discovered there. Listening to her, I was reminded of Dr. Finkleman’s Atlantis stories. Did the people of Akrotiri leave beforehand or receive a warning to escape? The true answer might forever remain a mystery, adding to its enchanting charm.

As we sailed along the vast cliffs of the caldera, we passed Nea Kaimeni (New Burnt Island), one of the still smoldering volcanic cones—inactive, but not extinct. We paused for a swim in the thermal springs near Palea Kaimeni (Old Burnt Island) before anchoring. Those who wanted to swim jumped into the warm waters, and I eagerly joined them.

Strangely, the water fluctuated from warm to cool, and we all joked about it. The bubbling underwater thermal springs created these warm patches, akin to a Swedish shower transitioning between hot and cold. The thermal springs were a reminder of the geological activity present below.

Time seemed to melt away as I floated on my back, gazing at the pristine blue sky Dr. Finkleman had often described.

After swimming, we enjoyed glasses of chilled Greek wine—both white and rosé—while resuming our leisurely sail. I felt engulfed by the tranquility of the day and the grace of our journey, almost as if the caldera was cradling us.

About 20 minutes later, we arrived at a cove with a home and a few makeshift structures, including two bright yellow boats. One resembled a covered dinghy, likely for transporting people to the mainland, while the other was a beautifully crafted gondola with red accents and a white canopy. Vaso introduced us to the story of Sostis, who lived there.

Years ago, Sostis fell in love with an Italian woman visiting Santorini, and they planned to marry. However, when she returned to Italy, he was heartbroken and settled in this cove, waiting for her return. The yellow gondola was the vessel he built for her. For many years, Sostis lived as a hermit until he turned 75 and fell ill, prompting his family to urge him to relocate to the mainland. Now, it’s uncertain if he will return or what will happen to his yellow boats.

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Our explorations around Santorini’s caldera included some of the finest Greek cuisine and delicious wine/Shutterstock

We took another swim here, though the water was cooler this time with no warm springs. Upon returning to the boat, we were served lunch, accompanied by more flowing Greek wine. Enjoying a spread of yogurt, tomatoes, refreshing Greek salad, and chicken kebabs freshly prepared on board, we perched at different spots on deck or around the shaded dining table. We joined a family of four at the bow, sharing the delectable meal, with juicy kebabs, crisp salad, and the delightful chilled wine.

Before we docked, Vaso shared one last surprise. We passed a small inlet harboring a tiny church. “This,” she explained, “is the Church of the Seven Holy Young Men,” dedicated to seven Christian youths from Ephesus, who defied the Roman conquests requiring the abandonment of their faith. Seeking refuge in a cave, they were discovered by the Romans, who sealed them within to perish. Legend suggests they did not starve, but instead slumbered for 200 years, awakening only when Christianity was revived in the 19th century.

As we made our way back to the dock, I found myself wishing the journey would last longer. If we could sail all day—or even as in the Odyssey, for a decade—I’d have welcomed it. I could understand how this land of mystery and beauty could inspire tales of unfulfilled love, heroes, and martyrs. I could easily envision Dr. Finkleman, now retired in this picturesque locale, soaking in all this stunning blue each morning.

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