Meet the “Artsy Aristotle” Behind Greece’s Palatial Calilo Resort

White stone facades, domed roofs of cobalt blue, influencers in billowing dresses, blocking the view: this is Greece in the popular imagination. A place to see a sunset, eat a salad, snap a pic… and, if you happen to be on the island of Mykonos, pay 40 Euro for a vodka soda.  

One man is trying to change that: Angelos Michalopoulos, an Athens native who owns one-third of the island of Ios, the peak-season tomato in the Santorini-Mykonos sandwich. Along with his wife, Vassiliki Petridou, and four of their five children, Michalopoulos has created a reason for discerning travelers to come to a splotch of land previously reserved for hippies and students: six hotels and restaurants, as well as a soon-to-come residential community, that cater to maximalists of all stripes. “We’re building something totally original, for people who appreciate beauty and nature but also want to have a good time and enjoy life,” he says, “which has been the Greek motto for like, 4,000 years—feasts, dancing, getting drunk, whatever else comes with it. That’s part of our DNA.” 

The Patek of his portfolio: Calilo, a resort on the southeastern edge of the island, a world away from the 18-and-up clubs that populate the island’s Chora, or main town. Over the summer, Calilo unveiled a palatial spa that includes a fitness center with mosaic walls and couple’s suites with words like “love” and “hope” stenciled in the ceiling. Corny? Not according to Michalopoulos, who designed every element of the property—“no interior designer, no architect, I do everything”—in accordance with his personal philosophies, which are detailed in 21 self-published books. His sculptures and Pop Art–style paintings (a highway sign announcing “happiness, next exit”) are scattered throughout his properties. His studio, he says, is “everywhere.” 

It’s quite the turn for a self-taught trader who spent two decades on Wall Street before carving out pieces of paradise. On a recent spin around Calilo, Michalopoulos explains how his two identities—wolf of Wall Street, artsy Aristotle—built a budding empire. Our conversation has been condensed and edited. 

When did you get interested in art and design?

About 20 years ago, I started writing and painting. It was really about opening paths into an audience to create beautiful feelings. I was interested when I was younger, of course, especially in what the ancient Greek philosophers had to say, but then I was in New York and working. New York is a very hard place to do anything but work.

Truly. What drew you to finance? 

The intellectual challenge of understanding where the investing crowd would go next, the immediacy of being right and wrong, and the excitement of living every day in a completely different set of parameters. I started trading when I was at Cornell University, and my first job is still the job that I have today—running the family office in Manhattan. We specialize in trading stocks, bonds, commodities, and foreign exchange. 

Are there similarities between your day job and what you’re doing in Ios?

Absolutely. Simply deciding to invest in Ios and develop it in a sustainable, unique way—we could’ve done something in Mykonos. But if we had done anything in Mykonos, it would have been a very boring exercise. I would’ve been yawning all day long. For me, what’s interesting is the fight. In Mykonos, it’s almost impossible to have a losing proposition. 

As an architect, what informs the layout of your properties? 

I want people to be surprised, and not just once—say you see a watch, for example. Any watch. It’s a surprise one time. When people go into a room at Calilo or Agalia—our boutique hotel by the port, we just finished renovations on it this year—it will keep on surprising them. The room will not be revealed in one shot. You’ll go from a tunnel to a bridge over a pool to a staircase to another pool, and so on. After five minutes, you’re so emotionally overwhelmed that you say, “you know what, okay, this is a vacation.” 

I was surprised by an inscription on a wall at Agalia: “Love is not wanting to defeat the one you love.” 

Most relationships are basically one person trying to defeat the other. People on vacation fight. Why? The expectation is high. I paid for these five days, I need these five days to relax. They suddenly mean more than any other time of year. But you have to choose your battles. 

What materials do you use?

Everything is locally sourced: the marble is excavated from this island, the swings are made of wood from olive trees. We use a lot of water, because water has freedom. It can assume any shape, which means lack of routine, which means unpredictability. It has a playfulness that can gently push somebody to feel playful without them understanding what’s happening.

Who are your properties for? 

We want to be an organization that can offer two not only distinctive, but almost opposing lifestyles: nature, slow pace, non-party at Calilo, and then at Agalia or at Pathos, our sunset club on the cliff, a much more vibrant, fun, energetic experience. 

For the latter, you’ve got to achieve the right mix. The older people, the rich people, the crazy painter with a crazy girlfriend. The 17-year-old that wants to show off her body, the guy that wants to show off his watch and his six pack. All of that has to be in the picture. If it’s only one thing, then it becomes geriatric, boring, artificial. You wouldn’t want to be part of it. 

What do you hope your guests leave with?

A sense that their problems are not as heavy or as negative as they were when they arrived. Ideally, they can reconnect to the truth of who they are versus the people that they are forced to be in their professional lives, which, in most cases, involves a lot of lying, a lot of faking.

How do you deal with that, personally? How do you balance being a trader versus an artist-philosopher-hotelier? 

Strong are the people who can face their weaknesses and weak are the people that hide them. I don’t hide mine. I’m heavily inspired by my defeats. You make money, you lose money. I embrace it.

(Images courtesy of Angelos Michalopoulos.)