Superyacht A happens to be sailing by at close quarters as I start interviewing owner Jason Pilalas during the St Barths Bucket. “It’s a pretty cool yacht, even though it looks like an office block on a raft!” he laughs, as we both gaze out to sea. I quickly learn that this is typical Pilalas. Despite a hugely successful (and serious) career in shipping and finance, he’s always ready with a joke and is clearly relishing hosting an official ‘committee boat’ at the St Barths Bucket. “My wife and I are people persons and we found out they needed a support vessel for the committee. It comes with perks; you get a spot in the harbour and you get to meet nice people, so we decided to do it every year.”

It’s not too far a trip across from North Palm Beach, Florida where Jason lives with Rena, his wife of 48 years, in a house “filled with maritime artefacts.” An avid marine art and history collector, Pilalas tells me that the National Maritime Museum in Greenwich is currently working with him on an exhibition – and, as if that wasn’t enough, their summer home in Connecticut is actually a renovated 19th-century lighthouse. Such is the force of his passion for the sea that, remarkably, he ran away from school aged 17, lied about his age and enlisted in the Navy, eventually becoming an officer. “I really enjoyed it despite the fact I had three combat tours in Vietnam,” he recalls, “but I saw lots of my friends get killed and it put me off making it my career.”

Instead, he pursued a career in shipping, quickly realising he was extremely good at it. “Shipping is a leaking bucket business; you load it, charter it, unload it and return it as fast as you can – any water left in the bucket is profit. It’s like chess, you have to think ahead three or four moves to make sure your ships are in position to take advantage of demand. I set some tanker chartering records which I am told still stand.”

When the company was ‘sold out from under him,’ it was time for a change. “I said to myself ‘everything I’ve done so far narrows me down, I need something to open me up again.’ So I got into business school, went to Harvard and got a Masters degree, which is fortunate as I’d never graduated from high school!” Pilalas went on to join The Capital Group Companies, a small investment company on the west coast and ended up working there for 36 years. By the time it was sold in 2009 they had grown it in terms of assets 800 times – and Pilalas, being a good sized shareholder, found himself in excellent financial shape for retirement.

Boating had always been part of Pilalas’ life and he’d previously dabbled with racing in an Etchells 22 –– but after retirement, an upgrade was on the cards. “I wanted to have some fun and travel, so I said ‘let’s get a boat, and we might as well get a big one.’” Of course, ‘big’ is a relative term – but for Pilalas, it meant 44m and M/Y Rena certainly feels spacious as we sit here chatting in the airy main saloon. There’s space for 12 guests across five cabins (each with a private Jacuzzi) and an impressive variety of outdoor living spaces to boot. For Pilalas, well-versed in all things shipping, the buying process was straightforward. “You never met a Greek that didn’t own a ship or a restaurant – commerce and negotiation are in our gene pool,” he jokes. “I knew what I wanted and what I was willing to pay.” Pilalas bought the boat during the financial crisis which he believes gave him a better deal and an interior refit followed in 2010 as “the previous owners had matched it to their private jet which wasn’t to our taste.”

Eight years on and the boat is still serving him and his wife well, although he admits that his better half did not originally share his passion. “My wife likes solid ground but we got the deal done by naming the boat after her! Now she seems to enjoy it quite a lot.” So does this mean another upgrade is on the cards? It seems there might be. Pilalas tells me he has ‘half an eye’ on some options, but as far as size goes, it couldn’t be too much bigger than S/Y Rena. “I want our boat to lie in front of our house when we’re in Florida, so if I do find another boat it can’t be too much larger as coming up Lake Worth by Palm Beach there are a couple of shallow spots.” Upgrade or not, the happy couple are planning to be back in St Barths for the Bucket next year. And I, for one, hope to be on board with these fun and friendly hosts once more.