On the Greek Island of Ios, Calilo Offers a Sweet, Surreal Dream

This beachside island resort is equal parts elevated getaway and ambitious conservation project.

ONE OF THE few things that can disabuse people of the dream of going to Greece from the United States is simply getting there. After two flights, a long cab ride, and one overstuffed high-speed ferry from Santorini, my husband and I arrived on the island of Ios feeling excited but unquestionably worse for wear. From the small town of Chora, we embarked on yet another 40-minute drive to the far side of the island, during which we passed groups of roaming goats and hillside churches. “There are 365 churches on this island,” our driver told us. “One for every day of the year.” By the time we passed through the gates of the resort and started our winding descent to the hotel, it truly felt as if we had crossed over to the other side of the planet.

Upon entering Calilo, you must first walk through what is essentially a tunnel of love — a long, curving walkway suspended above a shallow pool that leads you past stone walls weeping with trickles of water, an enormous red elephant statue covered in mosaic tile, and huge kinetic sculptures of human figures playing tug-of-war with an oversized bejeweled heart.

Aesthetically, the resort and surrounding grounds landed somewhere between Salvador Dalí’s iconic “Dream of Venus” and a more adult version of the set from “Pee-wee’s Playhouse.” Large, humanlike sculptures abounded — reaching out to one another, grasping for the sky. There was a curved stone staircase winding ever skyward and a tiny secluded chapel surrounded by a small reflecting pool. Every imaginable surface was tiled, including the various curved handrails that twisted throughout the property, looking like enormous strands of stone pasta. Given the austere surroundings — over 1,000 acres of stony hillsides traversed only by the occasional errant goat — Calilo felt like a surreal oasis.

Because we were on our honeymoon, my husband and I were tucked into the Passage to Love suite, which is situated near the top of the property. The 30 unique suites at Calilo are carved into a small mountainside, and a winding path leads you through the maze of private suites and villas before depositing you on a private stretch of beach. Our room overlooked the entire resort and had not one but three separate outdoor pools — one with a chaise suspended over it — as well as an entirely marble interior.

The visual fever dream on offer at Calilo is a fascinating contrast to what one might expect from a five-star Greek island experience: staid, whitewashed stucco, square infinity pools, and cool Mediterranean hues. While the resort is offering a remarkable high-end experience with gourmet dining, beautiful room amenities, and your own personal concierge, there is a sense of playfulness. While much of Greece feels chaotic and overly crowded, particularly in the high season, Calilo is designed for sublime privacy, which might be the greatest luxury of all.

The resort and its satellite properties are the brainchild of Angelos Michalopoulos, a Greek businessman and world traveler who sought to create a place that would reflect not only his creative sensibilities but also his commitment to sparing Ios from the fate that has befallen so many other Greek islands, which have been touristed to the very brink of ecological destruction. His wife and five children are all involved in some aspect of the resort, and Michalopoulos hopes the project will span generations.

In 2003, the Michalopouloses purchased more than 1,000 acres (essentially one-third) of the land on the 42-square-mile island, and made a pledge that the family would develop no more than 1% of the total acreage, leaving the rest in its natural state. In doing so, the family guaranteed that vast stretches of land and beach will remain untouched by hotels or cruise ships and that the 1% being developed will be done so in the most sustainable way possible.

As a part of his plan, nearly 70,000 trees have been planted across the island, including 550 ancient olive trees, some more than 300 years old, which were transferred from the mainland by boat. Michalopoulos’ wife, Vassiliki Petridou, maintains a donkey sanctuary near their home on Ios, where more than 20 unwanted, abandoned, or abused donkeys can live out their lives in opulent surroundings. Upon seeing them, I wanted to cry.

A few days into our stay, Michalopoulos invited us to the family’s private home, which is perched on a rocky outcrop at the very tip of the island. The home is like Calilo turned up to 11 — a sprawling mansion, multiple pools, an indoor fireplace as tall as I am, manicured rock gardens, and even more of the mammoth sculptures, all of which are created by Michalopoulos.

As we sat outside for breakfast, he shared his hopes for what people will take away from a visit. “It’s such a great experience to invoke beautiful emotions for people, whether that’s with a book or a poem or with a stay in a hotel. And if you can also preserve something at the same time, while really showing people the true beauty of this place and inspiring in them some feeling of joy or escape? That’s an amazing thing. That’s why I love this work.” He added in parting, “We just want to show people there is a new model for how they might do things.”

In addition to having built and designed essentially every aspect of Calilo, he’s also written several books of poems, essays, and plays, all of which espouse his philosophies on life, love, and the transformative power of joy. Before we leave the hotel, I spent time poolside with one of his books, “I Am the Child of My Soul,” which earnestly seeks to unpack what it means to live a fulfilled life, asking questions such as: “How much does it matter how old we are, since we do not know when our lives will end anyway? ... The more we enjoy life, the less we are stressed about when it will end.”

On our last day in Ios, the staff arranged a small boat to take us around the island. Our captain, who had packed a picnic lunch for us, brought us into tiny coves and sea caves, giving us a view of the island that is inaccessible to many people and remains remarkably untouched. At each stop, our boat went still, and we took a few minutes to jump into the crystal blue, albeit still somewhat frigid, water. I had almost forgotten what it was like to swim in water so amazingly clear, how much it feels like floating in the air. Soon enough we sped back, the boat hopping over the waves. In the distance, other Greek islands were misty, formless shapes on the horizon. Ahead of us, as if by magic, Calilo came back into view.