At Calilo, there is no minimalism. No subtlety. The entire property is an eccentric and eclectic reflection of visionary investor hotelier, poet, and conservationist Angelos Michalopoulos’s mind, a walk-through canvas embodying a philosophy he and the staff want guests to experience throughout every step.

Still, a sense of naturalism remains woven into the hotel’s story. That’s because Calilo has been carved from the cradling mountains, refined, and integrated throughout the property. From the 36 uniquely different suites to the elaborate three-story spa and fitness center, and the acclaimed Ches restaurant, much of Calilo is drawn from the dirt, sculpted, and breathed life by the Michalopoulos family.

Eden Awakened: From Arid Earth to Olive Embrace

The drive to Calilo follows a winding road up a rugged mountainside that’s arid, rocky, and scenic as it overlooks the Aegean Sea. It zigzags with switchbacks, offering lovely views of the cliffs dropping into the village and then the water. The road was bumpy for the first twenty minutes from the port until we reached a stretch of smooth highway that felt freshly paved, dulling the sounds of the road and leaving only the chaparral view. “This road is private,” the driver told us, which I would later learn is one of many improvements the Michalopoulos family had invested in the island of Ios, while still keeping much of it untouched and undeveloped compared to Mykonos and Santorini. This anecdote is essential to Angelos’s philosophy of life, which is more of a practice than philosophy, as the hotelier owns 30% of the land in Ios and has only developed 1% of it.

Upon entering the Calilo property, I witnessed the landscape shift from rocky and arid to lush and green, filled with blooming red flowers, prominent green succulents, and bushy olive trees reaching out and touching each other in a lively embrace of nature. I later learned that much of this vegetation didn’t exist before. In fact, many trees, including ancient olive trees over 800 years old, had been saved from deforestation and carefully relocated to the property, transforming what was once an arid valley into a vibrant Eden-like oasis. This meticulous and noble process truly reflects the theme at Calilo, which is displayed on a beautiful mosaic sign near the main building: “Create a Life You Can Fall in Love With,” the acronym from which Calilo derives.

Every Corner a Canvas, Every Stone a Story 

Throughout the property, I saw no wasted or unused space. A waterfall tunnel at the entrance combines Angelos’s own art with a wood-planked bridge over a gleaming stream of radiant blue water, creating a welcoming atmosphere unlike any other that wows and inspires wonder. All over the property, the ceilings are etched with messages of the Michalopoulos mantra, radiating light among shadows and filling every corner with little reminders of love. Using stones from the mountain, Calilo features a bounty of hand-placed mosaic pieces along the railings, pillars, and accents throughout the rooms, creating a harmonious balance between hospitality and nature. Mosaic messages of kindness and positivity, crafted from these mountain remnants, are also hand-placed along the walls and overhangs, leaving no stone unturned to fill guests with enthusiasm during their stay at Calilo. All these elaborate elements create moments that inspire positive emotions.

The Rebel Souls Heart Suite

No two suites at Calilo are alike. There’s no uniform layout or systematic blueprint guiding one suite to the next, almost as if each was drawn freehand and carved from the cliffside in a flow state guided by none other than Michalopoulos’s theme. I can’t describe them all, but I can tell you about my suite. It was the Rebel Souls Heart Pool One Bedroom Suite, and from the moment I walked in, it was all about love.  

The room began with a tunnel leading from the door to a bright glow where daylight waited at the end. It was filled with mosaic artwork of dolphins and waves, carefully placed by hand to echo the seafaring atmosphere surrounding Calilo. A bridge floating over a stretch of calm water cooled by the shade connected to the rest of the suite, where just beyond the light at the tunnel’s end, a stunning mountain backdrop awaited. There was also a playful arrangement of bubbling pools and, in the distance, the expansive ocean feeding into a private cove nestled at Calilo’s base.

The pools were plentiful and shimmered under the sun during the day and glowed a cool blue at night. There was an outdoor marble swimming pool complemented by a floating pillow that easily supported both our weights. We spent an afternoon lounging carefree on it, flipping over from stomach to back as needed to enjoy the sun. There was also an indoor marble pool with a double swinging bed that made for perfect sunrise viewing, as well as a hanging hammock bed that crested the surface of a covered pool. However, among the pools and streams of water connecting each peaceful spot, the most picture-worthy and enjoyable pool is the heart-shaped pool, the inspiring namesake of the suite, which offered an exclusive view of the entire property of Calilo, from the private beach and cove to the central facility and the lush vegetation that painted the grounds green.

At the Rebel Souls Heart Suite, there is no shortage of spots to rest and bask in the warmth of the Mediterranean weather, as the spacious suite offers many relaxing amenities, which we thoroughly used. A cool white cave with a swinging bed over water provided privacy and views of the distant ocean. We fell asleep on an additional outdoor bed shaded naturally by dried palm leaves and awoke up to a mountainous backdrop and the ocean darkening into a rich sapphire hue as the sun set behind Calilo. Each luxurious area was equipped with a place to hold a phone, camera, or speaker and a wall socket, a design that anticipated our every need and made this stay memorable and carefree.

Inside the room, stunning views stretch across floor-to-ceiling sliding doors, allowing the golden glow of morning to seep in. I recommend raising the blinds each night during turn-down service to welcome that gentle, warm glow of daybreak to awaken you each morning. Polished granite sheets in the bathroom gleam with luxury, and the marbled soaking tub offers a relaxing escape from the outside elements. Additional amenities include a standing shower, a TV (for when you’re finished admiring the surrounding natural beauty), and even an outdoor stone shower for bathing in privacy after exiting the pool. 

A Haven of Healing and Wellness

We spent three days at Calilo, experiencing something different each morning, noon, and evening, and still felt we could do more without repeating ourselves or growing tired of Calilo’s many offerings. One of the newer amenities is the three-story spa and fitness center that impresses from the first step. The entire facility is again decorated with mosaic murals promoting peace and positivity, with blue-lined flowers etched across the marble floors and walls, extending from the entrance and can be found in the bathrooms. A collection of tech-forward exercise equipment reinforces this level of detail, encompassing everything a fitness enthusiast desires from stair machines and free weights to an indoor pool for laps.

On the top floor, overlooking the lush vegetation and walking trails that stretch across Calilo, is the newly designed spa, where a nature-inspired room creates a sense of serenity unique to Calilo. Here, the artistic interpretation of nature again reflects Angelos’s eccentric style, showcasing his personal touch with the decorative tree, whose limbs reach into the far corners of the room. It stands center stage as the same glowing hearts and messages of love cut through the shadows from the ceiling and fall onto the babbling pool beneath a footbridge leading to the massage benches. The couples’ massage is perfected by a pair of masseuses who attentively work every muscular fiber, using heat and firm hands to release all tension, further enhancing this signature serenity that is found only at Calilo.

Paths of Solitude, Peaks of Light

Many trails surround Calilo, offering peaceful Greek coast hikes or runs that engage and strengthen all the muscles in your legs and core. I spent one morning running along the north side of the property, crossing the rocky terrain overlooking Calilo’s private Papas Beach, where this vantage point from the hilltop reveals clear blue waters glowing turquoise beneath the rising sun, illuminating the seafloor with shelves that rise and fall. I found several spots to pull off the trail, sit, relax, and enjoy the most scenic beach view—calm and serene, not crowded with beachgoers shoulder to shoulder, but peaceful bliss as beaches are meant to be.

There is another trail to the south that leads to Calilo’s own helipad at a higher mountain peak. This road has a steeper incline without any switchbacks or flat sections, making the climb more challenging with each step until the top, where I could once again see Calilo in its entirety, seamlessly blending into the mountainside and bathing in the sunrise from the east. The trail continues past the helipad into rocky terrain that rises and falls, splitting into segments that lead to different secluded coves or overlooks—always offering yet another great photo opportunity.

A Cove of Calm Beneath the Aegean Sun

One of the most unique and desirable features at Calilo is access to Papas Beach, a private cove with plenty of shaded canopies that resemble a charming cabana village from a distance.

Here, a beachside menu extends from Calilo Restaurant, where we ordered and enjoyed a trio of Mediterranean dips and charcuterie with local cheese, along with cocktails and mocktails served by friendly staff. We found peace here, relaxing first under the shade of dried palm trees in the canopy and then on a lounge chair facing the sun, listening to waves gently crash against the shoreline.

Cycladic Stories on Every Plate

Wellness is not only on display at Calilo but consumed through a menu of locally sourced and home-grown ingredients that celebrate the island of Ios as well as the rest of its Cycladic neighbors. Calilo Restaurant, in the main building, hosts an elaborate breakfast buffet that includes a bounty of options adding a Greek twist to Continental classics. I found that the capers and olives grown on site from the trees seen and admired throughout the property go well with the smoked salmon. The fruit salad features a wide selection of melons, grapes, and peaches harvested from their well-cared garden.  

Ches is undoubtedly Calilo’s premier dining experience and a must during any visit. Located just a short walk from the main facility, or a quicker trip in a cart courtesy of the staff, Ches is carved from a rock formation emerging from the ground, with much of its stony façade forming part of its foundation. Ches, an acronym for Create Happiness, Explain Sadness, reflects everything that makes Calilo so special. A backdrop of the private beach and the tops of palm trees surrounds the open-air dining patio. Mosaic tiles adorn the walls here as well, depicting seafaring adventures that add life and color to the sandstone surfaces. There is less seating, providing more space between tables and a more intimate experience with the intuitive staff who leverage their local knowledge of Ios and the surrounding Cyclades. But the food—a unique nine-course, chef-driven experience—is alone worth the trip to this secluded paradise.

I enjoy wine, drink it often, and although I’m far from an enthusiast or connoisseur, I highly recommend experiencing a wine pairing with the nine-course dinner. From my experience, the knowledgeable server guided me through each story about the wine, describing its Cycladic origin, lingering notes, and how it complements the next course—removing any need for prior wine knowledge. We started with a local sparkling wine, the Karanika Brut, described as a pure gastronomic sparkling wine because it was refreshing and tasteful, cleansing the palate without overpowering notes.

I could write at length about the menu, describing each note, texture, and how it reflects its namesake island. Each tasting offers enough sophistication and execution to stand alone as a flagship dish, and it’s a challenge to choose my favorites. But I’ll do my best to highlight notable flavors and stories. The tomato tartare topped with warm soda bread and sauced with Greek broth was a complex flavor profile and an excellent start. The broth was highly enjoyed with the tartare and made for easy dipping of the warm focaccia bread served early in the tasting.

The Shrimp Saganaki, a twist on a classic Greek appetizer from Kythnos, was a cool cannelloni pasta filled with shrimp mousse that exploded with flavor. The Sanotrini, a seabass tartare bathed in a citrus fruit dressing with lemons, limes, and kumquat, topped with a twill fish figure made from cuttlefish ink, and paired with a flava beans soup flavored with Mastika and bergamot, was well balanced, truly aromatic, and paired nicely with the Mysterio wine, a Santorini Assyrtiko made using wild fermentation, resulting in a unique orange tint.

The Ios dish was made with the island’s flagship ingredient, a Myzithra cheese, which was smothered over pasta, offering a hearty and savory spoonful I didn’t want to end. The Mykonos, a tasting of onion pie featuring a collection of stewed, caramelized, and fried onions, onion gel, paired with a skirt steak cooked over a Japanese grill that cooks it close to the coals to achieve a robust smoky flavor, made for a hearty closing to the savory options. And last, one of the closing desserts was an almond parfait topped with dark chocolate mousse infused with coffee and layered with a helping of olive oil to intensify the flavor, providing a sweet finish with a never-before-seen flavor profile.

Sunrise at Calilo. Video Martin Ramirez.

Moving Forward with Nature and the Community

The future is bright at Calilo with ongoing projects. Ahead of the 2026 season, which reopens in May 2026, Calilo continues to highlight what makes Ios so special while embracing the community and environment in their practice. Connecting hospitality with local culture, guests can observe or participate in the traditional art of cheesemaking alongside local herdsmen. This event, scheduled to occur three times a week, links Ios’s two main economic drivers, hospitality and farming. Calilo will also introduce a hilltop padel court, further promoting health and wellness with stunning ocean views.

And making its 2026 debut is another concept from the Calilo group, Lito. Opening on June 1, 2026, Lito’s central location near the island’s port and main village will offer guests and visitors the Calilo experience of exceptional service, private pools, and signature artful design in a retreat that’s more accessible than Calilo’s secluded paradise.

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 Cover Photo Courtesy Calilo

 Martin Ramirez is a brisket-eating, Shiner-loving, road-tripping enthusiast of all things Texas. This Dallas-born writer / adventurer is ready to take his ‘78 El Camino to find the best in food, fun, and fitness throughout the Lone Star State.