Most hotels in the Cyclades are run by a group with a logo. Calilo is run by a family with a sheep. Arriving guests tell stories of being greeted by co-owner Vassiliki Petridou herself, accompanied by her own sheep, which wears a glittering teal collar. It sets the tone for everything that follows.

Petridou and her husband, Angelos Michalopoulos, first crossed paths as Cornell students in 1983. Years later, they spent the better part of a decade of summers island-hopping by sailboat with their young kids, looking for somewhere to put down roots, and settled on Ios in 2003. These days their holdings cover close to a third of Ios, and they’ve vowed to put buildings on no more than a hundredth of that ground. The rest stays wild.

Michalopoulos, who made his money trading in New York before any of this, doubles as the hotel’s in-house artist. Nearly everything you see here, from the buildings to the oversized sculptures, came from his imagination, and he writes books too: plays, essays, verse. All five of the couple’s children now play a part in the business. Even the name is a family motto: Calilo is an acronym that spells out “Create A Life You Can Fall In Love With.” Petridou, meanwhile, keeps a sanctuary near the family home for more than twenty donkeys rescued from neglect, and this year the family opened a retirement home for elderly rescue dogs, too.

The hotel sits on Papas Beach, a private cove on the island’s quiet southeastern edge, about half an hour’s drive from where the boats dock, with some 1,000 wild acres all around it. Masons from the island built it largely by hand, using rock and marble quarried right there on the plot.

But the real reason to come is the rooms. There are roughly thirty suites terraced up the slope, no two alike, most with a pool of their own, and nearly all of them turned toward the Aegean. The floor plans are where the family’s imagination runs furthest. Sea of Smiles, a three-bedroom suite, has a pool pieced together from some 65,000 bits of marble; outside you’ll also find a cascade of water, daybeds that swing, a pond, and a shower cut straight into the rock. Higher up the hill, the all-marble Passage to Love suite gives you not one pool but a trio of them, and above one hangs a daybed you can lie on over the water. Other suites are built around heart-shaped pools, and one around a grotto-like pond. Whichever one you land in, the layout does the same thing: it pulls you outside, onto a terrace, into the water, and out toward that impossible blue.

This season brought new ways to spend the days. This year you can try your hand at cheesemaking alongside the island’s goat farmers, and a little flock of hens supplies eggs to the kitchen. Down on the sand there are twice as many loungers as before, while the spa now offers compression boots, a hammam, and red light sessions. In early September, it hosted a five-night padel retreat with New York’s Padel Haus, mixing day trips around Ios and spa time with lessons on court.

The family’s ambitions for Ios go well past hospitality. A share of every euro the group earns (4% of revenue) flows to its foundation, which is putting €2.5 million toward a tourism academy and community college so young islanders can train at home, €500,000 so that Ios, which has never had a fire station, finally gets one, planting 2,000 more olive trees, and backing research into the island’s water supply by a University of Athens team. That last project has history: years earlier, the family shipped some 550 centuries-old olive trees across from mainland Greece by boat, saving them from being chopped up for firewood.

And they’re still building, carefully. Over at the port, the family’s newest hotel, LIBU (shorthand for “Life Is Too Beautiful to be Made Ugly”), opened its first thirty rooms in August, most with private pools. Every one of its two-million-plus stones was laid by hand, and not a single building material was brought in from off the island. The family’s other addresses on Ios include Pathos, Agalia Luxury Suites, and Erego, their beach club. Which is to say: if you love Calilo, the family has plenty more for you to fall for.