Calilo i Grekland

Greece’s Palatial Calilo Resort

Angelos Michalopoulos has transformed the island of Ios with six hotels and restaurants, none more impressive than the over-the-top Calilo, a seaside resort with unapologetically maximalist leanings envisioned entirely by himself.

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.