Markos Chaidemenos on Growing Sunset Oia from One Catamaran to a Fleet of 25

In 2009, Markos Chaidemenos took a single Lagoon 500 out onto the Santorini caldera. Today Sunset Oia runs a fleet of 25 catamarans and yachts. In this edition of The Operators, he talks about hospitality, reviews, technology and why every new boat started with a guest request.

From hospitality to the sea

Before Sunset Oia and your other businesses, what was the first achievement that made you think, “I can build something significant”? Looking back, do you see a quality in yourself then that predicted what came next?

I think it began with being hoteliers. We grew up in hospitality, learning what makes a guest feel truly looked after, and that became the foundation for everything that followed. When we started Sunset Oia in 2009 with one Lagoon 500, the idea was to take that understanding of hospitality out onto the water. Sailing was what we loved. Hospitality was what we knew. Bringing the two together felt natural.

If there is a quality that connects it all, it is attention to the guest. That has not changed in seventeen years.

How did Sunset Oia begin, and when did you realise it could become much bigger than you first imagined?

Sunset Oia did not begin as a business plan. It began with a love for the sea. I have always been happiest on a boat, and yachting and sailing were part of my life long before they were part of my work.

That first Lagoon 500 was bought to share the caldera the way I saw it, with the island behind you and the sun going down. We were not thinking about market share. We were thinking about how that evening should feel.

It grew because guests felt the difference. They came for a sunset and asked for more: a full day, the hot springs, a swim at the Red and White beaches, a proper meal on deck, a crossing to Ios or Folegandros. Each new boat followed a guest request, not a spreadsheet.

The moment I understood it could be much bigger was when demand arrived before we had the boats to meet it. Today we have 25 catamarans and yachts. But every one of them still starts from that first Lagoon 500 and the same reason we bought it.

Building a position in Santorini

According to figures shared by some marketplaces, Sunset Oia represents 65% of the Santorini market on those channels. What did it take to build that position, and what is hardest about maintaining it?

Investment, above all. In our people first, because the crew is the experience. And in better catamarans and yachts, year after year. We also built real variety. Today our fleet of 25 covers a wide range, from more accessible shared cruises to the ultimate Ferretti yachts. Whatever a guest is looking for, there is a boat that fits, and it is run to the same standard.

The hardest part of maintaining it is that the investment never stops. A position like this is earned again every season.

Santorini has faced changes in demand. How does your strategy change when the market becomes less predictable?

For us the answer is always the guest. When demand becomes less predictable, we pay even closer attention to our reviews.

Reviews tell you honestly how you are doing, and they are what future guests read before they choose. If we keep the experience right and keep listening, the reviews follow, and so does demand. That is the one thing we never compromise on, whatever the market is doing.

Hotels, yachts and people

You have also invested in high-end hospitality. What have your hotels taught you about creating an experience, and what has the experiences business taught you about hotels?

They have taught me the same thing from two sides: the team and the guests are everything.

In a hotel or on a yacht, the guest remembers how they were made to feel, and that always comes from people. If you look after your team, they look after your guests. Everything else, the boats, the suites, the views, is the setting. The people are the experience.

Technology, data and instinct

You invested in technology early, while many tourism businesses still relied on familiar manual processes. What made you trust it, and which decision made the biggest difference?

For me technology was never the goal. It was a way to give guests a better experience and to make our team’s work easier.

Guests want to book quickly, get an instant confirmation and know exactly what to expect. Our team wants fewer manual tasks and more time with the guests. When a technology served both of those, the decision was easy. That is the test we still use today.

When you make decisions about pricing, distribution and capacity today, where do you rely on data and where do you trust your instinct?

Entrepreneurship has always been a balance between data and instinct.

Data guides our everyday decisions on pricing, distribution and capacity. Instinct is what tells me where to invest next, and what our guests and our people will want before they ask for it. The numbers show you where you are. Instinct shows you where to go.

Looking ahead

What do you think will change most in tours and activities over the next few years?

What will change most is the way people book experiences. It is becoming faster, more mobile and more digital, and it will keep moving in that direction.

The experience itself will not change much, and I think that is a good thing. A day at sea is still about the moments, the personal touch, the feeling of being looked after. Technology can make booking easier, but it cannot replace that.

If you were starting Sunset Oia again today, what would you do differently?

I would keep the reason exactly the same. Starting from love for the sea, not from a financial model, is the best decision we made. It shaped everything that followed.

What I would change is timing. I would invest in technology and data even earlier, and build the team structure before the growth, not during it. In the busy years our people carried the business on goodwill. Today we are much more organised, but I would have started sooner.

And I would think about our own brand from the first day, not only the marketplaces. They are essential, but guests should remember who took them out on the water.

What still excites you enough to start something new after everything you have built?

Honestly, the way I do business has always been turning a hobby into a business. Sunset Oia started from a love for the sea and sailing.

So what excites me is the same thing as always: finding something I genuinely love and building it properly, with the same care for guests and team. When you start from passion, the work never really feels like work.