With a family sailing history that goes back to the days of the original Nantucket Bucket, Robert Flaxman is the accomplished owner of Sunleigh, a 32.5-metre Jongert sailing yacht, competing in this year's St Barths Bucket regatta. A passionate sailor and expert of the event, Flaxman traces his own racing history and tells Elaine Bunting of BOAT exactly how to get the best out of the rarefied St Barths Bucket...
If you want to know the simple secret of the St Barths Bucket, this rarefied regatta with its humblebrag title, ask Robert Flaxman. “It’s all about having a good time,” he says. “It’s about sailing with some of the nicest sail boats on the planet and competing with the very best sailors in the world.”
Flaxman is the owner of Sunleigh, a 32.5-metre Castro-designed aluminium Jongert launched in 2002 and built for comfortable world cruising. Beyond its transoceanic capabilities, Sunleigh is a versatile performer, as the streamlined coachroof and unswerving sheer line suggest.
He has competed in the regatta six times in the last 10 years, and in 2024 was awarded the Wolter Huisman Memorial Spirit of the Bucket Trophy for his and his crew’s contribution to the regatta in aspects from sportsmanship and safety to hospitality and camaraderie.
Few owners enjoy their yachts more than Flaxman does or go back as far in superyacht racing, and that is an essential part of his unique perspective. His experience dates to the mid-1980s, when he raced with his father in the original Bucket, the Nantucket Bucket. A handful of big-boat owners had come to the little island next to Martha’s Vineyard to vie on a friendly basis and enjoy the parties and barbecues.
The event had been the idea of Nelson Doubleday, owner of the 38-metre schooner Mandalay, who put up a silver champagne pitcher as a trophy – the Bucket, because it rhymed with the place. The regatta had a purposely informal vibe, with crews made up of family and friends.
“We did everything ourselves; we didn’t have professional race crews – owners sailed their boats for the most part and it was my father, myself, my brothers and a skipper,” he says. “Everyone came out to have a good time. It gave the sailors something to look forward to.”
The Bucket was competitive, but the results were conspicuously rigged, and no one was allowed to win twice. “Nelson and some other guys would stand around at the barbecue, and they would say who wasn’t going to win. It was quite comical,” Flaxman remembers. “That was the beginning of it, but the difference between then and now is night and day.”
Four decades on, Flaxman steers his own yacht at the St Barths Bucket, the regatta that replaced its New England originator. He is an avid sailor, and lives on board for much of the year. “I love the boat very much, and I use it very heavily,” he says.
“My wife and I are on board every weekend from mid-May until October, Thursday to Sunday. During the summer months we sail on Long Island Sound and up to Newport, and in July and August we sail to Maine. During the winter we are in the Caribbean, going back and forth to New York.”
Most years, Sunleigh races in the Safe Harbor Race Weekend (formerly the Candy Store Cup) around Narragansett Bay, and she will be back at the St Barths Bucket again in 2026.
In Flaxman’s first regatta at St Barths in 2015, Sunleigh was entered in the Corinthian Spirit class, the white sails-only division that steers around the complexities and crew requirements that spinnaker handling dictates. “I had my parents, my captain, my mate and myself, and we did it on our own. We got crushed, of course, but I do it for enjoyment knowing full well I’m not going to win, and I enjoy the sailing,” he says.
But after that first year, he and his crew plunged into the full-fat racing divisions, where the zeal for victory can be intense.
Most owners are, by nature, ultra-competitive and driven, so striking the right balance between desire to finish first, sail safely and have fun whatever the outcome can be tricky for the organisers. The greater the will to win, the higher the stakes and the greater the need for more professionals on board.
“A lot has changed,” Flaxman notes. “My boat is almost 25 years old and by today’s standards is slow; the designs of today are so much more advanced. There are 130-foot [40-metre] boats with carbon hulls, masts and rigging that weigh less than mine, and that is a different ball game altogether. They are sailing at 13 to 14 knots all day and some of them are pushing 17 to 20 knots. That is amazing at those sizes.
“The price tag that goes along with it has changed,” he continues. “You’re looking at $30 to 40 million or more for the yacht; that’s another level. The professional crew get paid big dollars. You have to have the right crew, get airline tickets for 20 people, accommodation for them, feed them. You’ve got to have the right sails on the boat, ensure that it is set up to go racing.
"The preparation to go down there is huge. The rock star sailors of the world are showing up on these boats, they are getting paid well to do it – and then they get to party in St Barths for the weekend,” he laughs.
Flaxman pitches his ambitions somewhat differently. “I’m doing two races a year. The rest of the time I’m cruising with my boat and I have all captive winches, so if you have to sail my boat with two people you can do that. With these other boats you can’t.
"That becomes a question of give and take: do you really want to give up the cruising aspect of it for these races, or do you want to take your cruising yacht to go racing? It’s two different types of philosophy.
“I have got a group of people I sail with, with only one or two professionals. [The pro sailor] Diego Fructuoso is good friends with my captain and has come over the last couple of years and sailed with us. He is from Spain and has been involved with Spanish Olympic teams and SailGP. And I have Tom Webb from North Sails Europe. But mostly they are people I know from Newport who have recent experience.”
In 2025 Flaxman had Sunleigh re-rated to gain a more accurate handicap. “We’ve had the hull scanned and they did a righting test. So now that the boat has been rated properly, I hope to be competitive as opposed to going into the race with the goal not to finish last,” he says. “Now the goal is to place.”
The level of competition and the roll call of elite sailors imbue Bucket racing with an added glister and glamour that everyone appreciates. It showcases new design ideas and serious levels of commitment and skill. But the secret to getting the best from it all, Flaxman insists, is to keep in mind that trophy winning is a bonus, and there is as much to be gained from the entertainment and fellowship ashore.
“You know what the spirit of the Bucket is? I show up and I race the boat to the best of our abilities, but at the end of the day we are there to have a good time, to be safe. My captain will do his speech to the crew before the start, and I finish up by saying to everyone: Come back with 10 fingers and 10 toes. Safety is a big thing for me. It’s only a trophy. The main thing for me is to bring everyone together that I like to sail with and have fun.
“I really enjoy all of it, from the minute I land in St Maarten. The practice days, the breaking each other’s chops on the boat, the going out, having a crew dinner on the Saturday night – all of it. I sail in the classes that they put me in, and I try not to take ourselves too seriously.
“Am I happy with the results all the time? No. Sometimes if it doesn’t go well, I wonder why we bother doing it, but you suck it up, and you do it with a smile on your face.” The day’s races and crew teamwork, followed by a party, a casual dinner among friends or other sailors, the famous owners’ party at Nikki Beach: these are the ingredients that make it a fiesta at
the tail end of the New York winter, set in an environment with no sales activity, no promotion, no commercial hustle.
“Competing in St Barths with the best sailors in the world? It doesn’t suck – it just doesn’t. The restaurants and bars are great; it’s a nice island to be on,” says Flaxman. “And when you look around at the boats you’re sailing against, you just think ‘Wow, I’m here, I’m doing this.’”
Read More/All the yachts competing in the 2026 St Barths Bucket