BORN VOULA, ATHENS, 1977
LIVES BY THE SEA IN VOULA, ATHENS
CHILDREN TWO (13 AND 11 YEARS OLD)
OCCUPATION SHIPOWNER AND SHIP OPERATOR
BUSINESS DRYDEL SHIPPING
FLEET SIZE 12 IN WATER; 11 ON ORDER; 45 OPERATING

It would be easy to imagine that the life of a second-generation shipping magnate had been mapped out well in advance. That, destined to take over the reins of the family business, actual love of the job was never part of the equation. Nothing could be further from the truth in the case of Costas Delaportas, who runs a fleet of bulk carriers as well as a 41-metre Mondomarine yacht.

“As a teenager, during the summers, while others were out enjoying holidays, I would spend more than two months in the office,” he says. “Not because I was told to, but because I admired my father and I wanted to be there. I was genuinely interested. It never felt like work – it still doesn’t – it felt like a passion already taking shape.”

It wasn’t all work, though. When he was about 10 years old, the family started to spend part of the summer holidays on a small 12-metre motor yacht, exploring the Greek Islands. “I remember leaving the marina for the first time, feeling the wind on my face and seeing the coastline slowly fade behind us; it was exciting and completely new,” he says. “Those early days were all about learning. I started to understand the weather, how to navigate and how to anchor safely.

“But what I remember most is simply being on the water with family and friends. Even ordinary tasks, like preparing meals on deck or dropping the anchor, felt special. Sailing in the Aegean at that age made me realise that yachting isn’t just about the boats – it’s about spending time together and creating lasting memories.”

Yachting cemented Delaportas’s dawning fascination with ships and the sea, and his next steps came quite naturally. After studying commercial shipping operation at London Guildhall, he began working under his father Dionysios at Meadway Shipping & Trading in 2002.

The heart of the operation was in so-called dry bulk – shifting cargoes such as coal, iron ore and grain. He brought brimming energy and a ready smile to the business, and by his early thirties he was pushing to expand with a network of operating centres, which now stretches from Singapore to Houston. These days he runs the business under his own DryDel brand.

“For me, Greece is the perfect place to be with Maestro in the summer. It has everything I want from yachting”

“The commercial side of the business has always excited me and still does today. I love making deals, and the day-to-day of chartering and fixing gives me that satisfaction,” he says. Delaportas has certainly been busy with deals recently. In July 2025, he “flipped” a five-year-old bulk carrier for $34 million (£25m), generating a tidy $3.5 million profit in the process. A year earlier, he sold several ships rather well, including a 61,000DWT bulk carrier for $21 million, reportedly doubling his money in just 18 months.

But it isn’t just speculation – he is also going long on new building, betting that his young fleet will be well positioned to hoover up growing demand for tonnage between Africa and China.

Just before Christmas, DryDel signed a fourth contract for a so-called Capesize bulk carrier – a monster vessel of 290 metres LOA and a 45-metre beam capable of shipping 182,000 tonnes of cargo. Due for delivery in 2029, it is one of 11 new ships currently on order for DryDel – all naturally IMO Tier III compliant. Since 2019, the business has invested more than $800 million in new builds.

“The business has gone through significant transformation and growth,” he explains. “We moved from being a solid family shipping company to a more modern, globally diversified ship-owning and operating group with a strategic commercial focus.”

Part of that transformation came after the passing of his father, a time at which he matured quickly and deeply, and which led him to pursue his own path. With the company entrusted to the next generation, Costas decided to create his own shipping Company, DryDel Shipping, and to follow a distinct, growth-led vision focusing on modern tonnage, new builds from top Japanese yards and the expansion of operating offices worldwide.

Far from commissioning new boats, he has consistently scouted out second-hand talent and added value through refitting. This was the case with his first-ever yacht, a 21-metre Uniesse motor yacht called Legend, which he only acquired when he turned 38.

“I found her in Croatia and brought her to Greece,” he says. “She was particularly successful in charter thanks to her layout, offering four guest cabins with en-suite bathrooms – something quite rare for a yacht of that size at the time.”

Next came a 34-metre Canados, called Mamma Mia (ex-Ermitage), purchased in Monaco in 2020 and then relocated to Athens. “This was a significant step up in both size and profile, and she performed very well commercially. From the outset, I was interested in yachts that could combine personal use with strong charter potential,” says Delaportas. “I kept her for around two years before selling her to buyers in Turkey.”

He took another step up in 2021 to buy a 40-metre Maiora, also named Mamma Mia (ex-Melina C), which also remained with him for two years and would be the largest yacht/project he focused on for chartering before the Mondomarine Maestro, (ex-The Shadow), purchased in 2023.

“I have always paid attention to choosing distinctive, memorable names and to selecting yachts that work well, both emotionally and commercially,” he says. “Over the past decade it has very much become a passion business for me. It began with a personal love for the sea and time on board but gradually evolved into something more structured and professional.”

The parallels with the trading side of DryDel are obvious. “In many cases I have been able to make a profit when buying and selling yachts,” he admits. “But it is not trading-for-profit in isolation. Like with my commercial fleet, it comes down to discipline and timing: buying at the right level, choosing yachts that remain commercially attractive, investing in the right upgrades and keeping the asset in top condition, so it is always sellable.”

He enjoys the full process – from identifying the right yacht at the right moment to upgrading, managing and positioning her correctly in the charter market. This was the case for his latest yacht Maestro, a muscular 41-metre with a top speed of 18 knots. “I bought her in 2023, the timing largely driven by opportunity. The price was very attractive for a yacht built in 2013, so from a value perspective it made a lot of sense.

“What really appealed to me was the overall balance she offers. The triple-deck configuration creates excellent flow and generous guest spaces, which works extremely well both for private use and charter. Her size is also ideal for the Greek Islands: she’s large enough to feel substantial and comfortable, yet she is still perfectly suited to island cruising, anchorages and typical itineraries.”

Maestro is Delaportas’s first aluminium yacht, and he likes the performance and speed that the lighter metal offers. But there was still plenty of work required to get the yacht up to charter standard. After a trial season of private use,the yacht was dry docked in Perama, Athens, where Delaportas could closely oversee an ambitious €4 million (£3.5m) refit programme that ran from a new interior to Starlink and a technical overhaul.

“We gave her a full exterior repaint,” he says. “The original colour scheme was very dark, in black and grey, which is why the previous owners called her Shadow. For the Mediterranean, I felt the yacht needed a lighter and fresher look, so we repainted her entirely in white – a very Greek colour that matches perfectly with the blue of the Greek sea and the natural light. We also reconfigured the guest accommodation from five cabins to six and upgraded the jacuzzi on the top deck.”

Not one to miss an opportunity, Delaportas also had his favourite architect, Apostolos Molindris, rework the interior styling. “Before the refit, the yacht felt heavy and dated, with older furniture and finishes such as yellow marble that no longer suited the style or experience I wanted to create,” says Delaportas. “The main objective was to give the yacht a more minimal and modern look, while also improving the layout and functionality.”

He hand-picked pieces from top Italian brands – an armchair from Maxalto, a coffee table from Paola Lenti, lighting by Flos. From Burgess’s glossy charter brochure, it is clear that Maestro has been given a new lease on life. Pale woods, cream leathers and mocha-veined white marble seem to catch and amplify the Greek sunlight. And as he recounts the tale, Delaportas exudes an equally sunny sense of relishing the process.

He has also been scrupulous in curating a wellequipped toy store. Besides a four-metre Williams tender there’s an Axopar 37 chase boat, which serves to put waterskis, wakeboards and towables to good use, then an array that includes jet skis, sea scooters, an e-foil, jet surfboard and various inflatable boats and platforms.

He’s clearly a man who enjoys a turn of pace. “They each give a different kind of fun – e-foil for something new and smooth, waterskiing for speed and challenge and jet skis for pure freedom.”

And while some owners dream of setting off to explore distant shores and cultures, Delaportas is already exactly where he wants to be. “Honestly, I don’t really have a bucket list,” he says. “For me, Greece is the perfect place to be with Maestro in the summer. It has everything I want from yachting: stunning islands, crystal clear waters, variety in short distances and the perfect setting to spend quality time with family and friends. When you have that combination at home, you don’t feel like you are missing out!”

His perfect day aboard begins with an hour pounding the yacht’s treadmill. “There’s something special about training in complete privacy while the yacht is under way, watching the water and the horizon.” Then it’s a simple breakfast on the upper deck and the rest of the day spent engaging with the sea and surroundings. “In the evening, we usually go into port and keep it simple in the best way: a Greek taverna, good local food and a long dinner with the people I care about.”

That said, there is one dream he would indulge if possible. “I would invite Aristotle Onassis,” he says, referring to perhaps the greatest Greek shipping magnate of all time. “I’d love to have him aboard Maestro, sit on deck with a cigar, and talk about shipping – how he built his vision, how he read markets and people, and how he would approach the industry today. For me, that would be a unique, unforgettable conversation in the perfect setting.”

First published in the April 2026 issue of BOAT International. Get this magazine sent straight to your door, or subscribe and never miss an issue.