There’s nothing like starting at the top. While some come to superyacht ownership in gradual steps up the size range, the stunning 49.5-metre schooner Eleonora is Zbynek Zak’s first yacht. And it started – as a purchase often does – with a charter. “I wanted to charter a classic with my wife, having retired from the business we were involved with at that time. We both like classic things, but this was our first large-yacht charter, so it had to be special,” he says. They were introduced to then-owner Ed Kastelein, who’d built Eleonora in 2000. “We signed up for a charter and few days later, Ed contacted me to say that the boat was available to buy,” says Zbynek.

It wasn’t quite job done – there was careful negotiation and due diligence, “and securing the experienced Ed as skipper for a six-month transition period”, says Zbynek. With Ed guiding them along the learning curve, they got to understand their new purchase, and it was proving a perfect match between yacht and owners. “In a world where everything is touchscreen and hi-tech with carbon-fibre spars, we wanted to experience sailing in the way it was done 100 years ago. The feel of real wood, holding the lines and sheets securing huge sails, and a classic-looking interior are hugely important,” says Zbynek.

He sees his role as custodian as much as owner: the yacht is a faithful replica of the famous schooner Westward, launched at the Herreshoff yard in the US in 1910. “The great history was one of the key considerations when we purchased Eleonora,” Zbynek says. One of the best-performing racing schooners in the world, Westward saw off the likes of Britannia, Lulworth and Meteor II in racing events. The modern yacht, steel hulled and wooden masted like the original, was built at the Van der Graaf shipyard in Holland. “The interior is made using old-fashioned carpentry skills, and wood, lots of wood!” he says.

But as a custodian he is not an owner who treats his yacht as a museum piece – she has covered a lot of sea miles. “We have taken Eleonora all over the Western Mediterranean, to Scotland, Ireland, southern England and to the Caribbean on a couple of occasions,” he says. “In 2008 we spent the summer on the east coast of America, starting in Florida and spending a month sailing off Newport, RI. We came into New York harbour under full sail, sailing downwind towards the Statue of Liberty, where the US Coast Guard informed us we were too close to the historic landmark, but they also wanted to board us out of curiosity and interest!”

One of the highlights last summer was a cruise down the west coast of Italy. “Sicily is a spectacular place – the wine, the food, the history. Syracuse is a great place to stay and Stromboli erupting at night-time is simply breathtaking from the deck of the yacht,” he says. A visit to Venice the previous year also provided a highlight. “We were allowed to moor right in front of St Mark’s Square. It’s a spectacular place to visit. We left under a full set of sails down the main canal,” he says.

For all their great cruising adventures, he and his wife are equally happy with their local cruising grounds. “We live for part of the year in the South of France near Marseille and we like to visit the old port with Eleonora. It is always a special experience sailing in and out of this historical location,” he says.

Racing or cruising, Eleonora has proven an excellent choice. “She’s a fast racing machine, but is equally as comfortable cruising during holiday voyages. Some smaller classic boats are dayboats, but with Eleonora you can spend weeks cruising in great comfort. All the amenities are on board, including heating for Scotland and air-conditioning for warmer climates!”

With a full-width master, two doubles and a twin, the yacht sleeps eight and never feels crowded in cruising mode, and there are plenty of spaces on deck for guests to enjoy. “One of our favourite spaces on the boat is just in front of the wheel – an ideal spot for reading a good book. In the morning and evening we like to stay between the two masts. We set up a dining table and the atmosphere is just magical. We also occasionally lie on deck chairs just looking out to sea,” says Zbynek.

He ensures the yacht is an occasional participant in racing events, including last year’s Round the Island Race in the Solent. Although he calls himself “an absolute amateur” he clearly enjoys a turn at the helm. “Fortunately, we have a very experienced captain, tactician and navigator always on board for racing. The Corinthian spirit of these Big Class classics is very different to, say, racing J-Class. We do not pay salaries for rock star helmsmen and crew. Much of our race crew is made up of enthusiastic and skilled volunteers, typically our friends. The permanent crew is nine people. Add 30 or more race crew, and let’s go racing! I enjoy the logistical challenge of bringing it all together for the regattas,” he says.

Last summer on the Solent for the Westward Cup proved particularly memorable. “To have your boat on moorings just outside the Royal Yacht Squadron is a magical sight,” he says. For last year’s Round the Island Race, Sir Ben Ainslie joined Eleonora. “At one point we were both holding on to the wheel. We had great fun and he is a very nice English gentleman. We were by far the largest of the 1,600 yachts, which made the start challenging, but eventually with a good breeze we made good time. As we were running through the Eastern Solent towards the finish line, the Isle of Wight car ferry slowed to let us pass. The locals on board told me this had never happened before! That left us with one tack to the finish line. We had the time of our lives.”

Retirement means that Zbynek and his wife spend three to four months on board every year, with racing limited to a few regattas. “We select well-organised regattas that include comparable-size classic boats, like Elena and Mariette. The owners of some of these are good friends and, of course, also well-respected competitors. In the past we have invited young members of the New York Yacht Club and the Royal Yacht Squadron to race on board with us. It’s a great opportunity to introduce young sailors to classic sailing – these are future hard-working crew members,” he says. Otherwise, it’s just a case of choosing to be on board when the yacht isn’t on charter. “We love to entertain friends and share good food and wine,” says Zbynek. “Our French chef Patrick, who is also available with the charter, is exceptionally talented. My wife spends time in the galley picking his brains about different recipes, and we love to visit the local markets to help buy the fresh produce.”

This is certainly a yacht that’s appreciated in every aspect. When Zbynek Zak says “by owning a yacht like Eleonora you are keeping history alive for new generations, preserving the legacy of being able to race a classic”, you sense the eye of someone who can appreciate the beguiling effect of the past in today’s furious modern world. But in the same breath he says: “Size does not matter in yachting. It is all about the fun and excitement of being on the water. You can have as much fun on a sail-board – it’s just that Eleonora allows for a greater number of people to be present and to have fun at one time. For me, owning Eleonora is a passion, not an expensive show-off hobby.” Never, in other words, has history been so much fun.

Eleonora charters through Yachting Partners International (YPI) from €65,000pw. She is available on brokerage through Edmiston, asking €7.95 million. For more images click here: