As one of Santorini’s leading names in luxury yachting, Caldera Yachting has become synonymous with discovering the island from a different perspective — away from the crowds and from the familiar paths of land. But behind the yachts and unforgettable Aegean views lies a story of ambition, dedication and a distinctly Greek approach to hospitality.
This August, Chic Icon met with Yiannis Matthaios, the CEO of Caldera Yachting, for an exclusive conversation in Santorini. In our interview, Matthaios reflects on the journey that has shaped Caldera Yachting, the philosophy behind its success and the changing definition of luxury at sea. He also shares his perspective on the future of Santorini, the evolving expectations of today’s discerning travelers and the importance of preserving the authenticity of the destination that remains at the heart of the company’s identity.
Caldera Yachting has become one of Santorini’s most recognized names on the water. Looking back at your journey, what was the original vision behind the company, and how has that vision evolved as you have grown?
When we launched Caldera Yachting in 2009, the yachting scene in Santorini was very different. Our original vision was simple yet ambitious: to bridge traditional Greek seamanship with high-end hospitality. Travelers were not simply looking for transportation across the water; they wanted an immersive experience where every detail, from the itinerary to the cuisine and service, was thoughtfully curated.
Our founding motto was “The Experience of a Lifetime.” From our initial two vessels, we have grown into a diverse fleet of more than 25 catamarans, motor yachts, sailing yachts, speedboats and traditional boats. We later expanded to Athens, bringing the same philosophy to the Athenian Riviera and Saronic Gulf. Today, our vision remains rooted in uncompromising quality, safety and authentic service. Our awards and guest ratings remind us that excellence must be earned with every voyage.
The Santorini’s caldera is one of the world’s most photographed destinations, yet every guest hopes for a unique experience. How do you ensure that each voyage feels personal and memorable rather than simply another sightseeing cruise?
In an iconic destination like Santorini, personalization is essential. Guests should feel they are creating their own experience on the water.
Our crew is at the heart of this philosophy. They are highly trained mariners and local insiders who know hidden coves, swimming spots, and the changing Aegean. They adapt the experience to each guest.
Food is central to the journey. Fresh local Greek cuisine and regional Santorini wines transform dining against the caldera into a complete sensory experience. Ultimately, we are not simply offering a boat trip; we are creating an environment where guests feel cared for, unhurried, and deeply connected to the sea.
Is there a core value or guiding principle that has influenced every major decision you have made since founding Caldera Yachting?
If I had to reduce our philosophy to one principle, it would be operational integrity built on uncompromised respect: for our guests, the sea and our team.
For our guests, luxury is ultimately about how you make someone feel. Every decision is guided by our responsibility to protect the trust people place in us. Respect for the sea means safety can never be compromised, so rigorous maintenance, crew training and international certifications remain priorities. Finally, our people are fundamental. We invest in their development and well-being because authentic service begins with the team.
In a destination with many yacht operators, what truly sets Caldera Yachting apart?
It is not one single element, but the way everything comes together. We combine a diverse fleet, highly trained crews, operational reliability, and a deeply rooted Greek hospitality culture.
Our fleet ranges from semi-private catamaran cruises to exclusive private experiences aboard motor yachts, sailing yachts and speedboats, as well as multi-day crewed charters. Regardless of the vessel, our standards remain the same: safety, fresh dining and attentive service.
The heart is our people. You can purchase a beautiful yacht, but not genuine warmth or philoxenia. Our crews anticipate needs and make guests feel welcome. Behind the scenes, dedicated maintenance facilities, international certifications, and continuous training provide the reliability and peace of mind luxury travelers expect.
Luxury travel today is increasingly defined by authentic experiences rather than extravagance alone. How has Caldera Yachting adapted to changing expectations?
Modern luxury has changed dramatically. Travelers today are less interested in ostentatious displays and more interested in authenticity, privacy, connection, and meaningful experiences. We adapted by redefining luxury on the water as something immersive rather than purely material.
What guests value most is often the simplest thing: authentic human warmth. They remember the crew, the secluded cove, the meal prepared onboard, or the sunset experienced without feeling rushed. Privacy and space have also become some of the greatest luxuries.
Above all, guests seek emotional memories. A proposal, family celebration or swim in the Aegean can stay with people long after they leave Greece.
Is there a particular guest story that perfectly captures what Caldera Yachting is all about?
Over the years, we have welcomed celebrities and royalty, but some of the most meaningful stories are deeply personal. One that remains particularly memorable involved a guest who booked a private sunset cruise in memory of his late father, who had spent his life at sea but had never visited Greece.
The crew sensed how emotional the journey was for the family and, without making the moment overly formal, our captain navigated to a quiet, secluded cove away from the crowds. As the sun disappeared behind the caldera, the crew raised a heartfelt toast with the family in his father’s memory.
Afterwards, the guest told us that it was not the scenery or yacht that made the experience unforgettable, but the empathy and intuition of the crew. For us, that story captures the essence of Caldera Yachting. We are creating moments that become part of people’s lives.
How have guest expectations changed over the past decade, and what defines luxury yachting in Santorini today?
Guests have moved from passive sightseeing towards purposeful, highly personalized and increasingly conscious travel. They want privacy, secluded locations, authentic cuisine, professional crews and a deeper connection with the destination.
They are also more informed about safety, sustainability and vessel quality. True luxury is not simply about appearance, but responsible and professional operation.
In Santorini, luxury today means having a private space away from the crowds, enjoying exceptional local food prepared onboard and experiencing the caldera at your own pace. It is about slowing down and allowing the beauty of the Aegean to become the focus.
Looking ahead, what is your vision for the future of Caldera Yachting?
Our future is about controlled and meaningful expansion, while deepening our commitment to sustainability, innovation and bespoke experiences. Following our expansion into Athens, we are developing multi-day crewed charters from both Santorini and Athens, giving guests the opportunity to explore Greece beyond a single destination.
We are exploring greener fleet operations, including more eco-efficient propulsion, reducing single-use plastics and supporting marine conservation. At the same time, we are developing new experiences, from private sea-to-table culinary journeys to wellness-focused morning cruises incorporating yoga, quiet bays and organic local gastronomy.
Technology also plays an important role. Digitizing bookings, payments and communications improves efficiency while reducing paper waste.
When you imagine the future of Santorini as a luxury destination, what role do you hope Caldera Yachting will play?
We want Caldera Yachting to become a benchmark for sustainable maritime hospitality, showing that luxury and responsibility can coexist.
Santorini needs a more considered model of tourism that respects the island’s capacity and protects its marine environment. We hope to contribute by embracing greener technologies, reducing waste, supporting local partnerships and encouraging more private and small-group experiences rather than high-density tourism.
Most importantly, we want luxury to remain connected to Greece: its sea, cuisine, traditions, people and legendary hospitality. If we can help guests discover Santorini not simply as a beautiful destination, but as a place they genuinely connect with, then we will have achieved what we set out to do in 2009.
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