A Swan owner on helming at the Bucket and round-the-world plans

As a teenager in the mid 1980s, Hillery Head watched the boats sailing from the Port de Gustavia from the front deck of her family’s holiday home in awe. The island was different back in the day. “The electricity went off at eight o’clock and didn’t come back on until the next morning,” she recalls. “ There were no telephones, either. If you wanted to call someone, you had to stand in line at the post office.”

In March, Head ticked off a long-awaited goal by attending the St Barths Bucket for the first time, where she helmed the races herself aboard her 30.2-metre Nautor Swan, Onyx II, which she took delivery of in November 2025. Though much has changed since her younger years spent viewing the sailing boats from afar, the event was something of a full-circle moment for the American yachtswoman. “

This was my first Bucket, and our first regatta with Onyx II, so winning our class was fantastic,” says Head, who was joined on board by a handful of seasoned sailors. “It was the Corinthian Spirit class, so we had quite a light race crew, but they were a fabulous team who had all worked together before. All I had to do was steer.”

Already pleasantly surprised by the yacht’s competitive edge, Head also kept a watchful eye on her competitor’s tactics during practice to help sharpen her approach. “I observed what the other boats were doing and applied some of their methods,” she says. “Suddenly everything clicked.”

The crew stood out for their vibrant tie-dye T-shirts designed by her broker’s daughter, which quickly made Onyx II the fleet’s most recognisable entry – “We were a burst of colour and a boat full of smiles.” Head also drew attention as the sole helmswoman in the fleet.

“It was interesting to be the only woman,” she muses. “I know there are others, it’s a shame we missed each other this time, but coming from the construction supply industry, that’s not a new feeling for me.”

Born and raised in Birmingham, Alabama, Head spent her summers at her family lake house sailing aboard her father ’s 16-metre Hank Hinckley. “My dad was a keen sailor, and I grew up sailing on that boat. We’d cruise up the north-eastern coast, head south to the Caribbean and on to Europe, even Scotland and Scandinavia, on occasion,” she says.

She studied at Yale University beforegraduating from Washington and Lee law school in Virginia where she met her first husband. “He was a lawyer, and we moved back to Birmingham where I joined my family ’s construction supply company, RAM Tool, and developed a strategy for expansion.”

Under Head’s leadership, RAM Tool grew from five local branches to 43 locations nationwide, significantly expanding the company footprint. “Somehow, in the middle of all of that, my husband and I were blessed with three children,” she adds.

“We were a burst of colour and a boat full of smiles”

When her husband passed away from pancreatic cancer, Head was approached by a competitor with a buy-out offer for the business. “It was just after Covid-19, and I realised there was still so much life out there that I could choose to live,” she says. “It was the right time to step away.”

With the company sold and time on her hands, days were spent on long horseback rides with her children, skiing with the family in Aspen and cooking large meals together at home. Sailing also became a priority. “I like to do anything where I can be with the people I love,” she says.

She’d inherited the Hinckley in 2011 and had continued to sail the boat out of Charleston, battling the area’s strong tidal currents and frequent afternoon thunderstorms, not to mention the familiar Caribbean cruising grounds of her youth. Yet as time went by and the children grew older, their sailing adventures became increasingly ambitious.

“We hired a full-time captain, but that was another person that needed accommodating. It felt like the boat became smaller and smaller,” she says. “My youngest has just graduated, my middle son was in Nashville with his wife, and my eldest lives in Birmingham. I’ve remarried, and my husband has four daughters, so between us we’re at seven kids.”

Naturally, she began dreaming of a bigger boat that could accommodate a circumnavigation with her growing family. Head was introduced to Fraser broker Matthew Lester in the summer of 2025 who took her yacht shopping in Cannes and Monaco. “I hadn’t been aboard many boats and when Matthew got wind of this, he grabbed me by the hand and we climbed on and off a million yachts – old ones, new ones, all sizes – trying to ascertain what appealed to me.”

In September, she was invited to sail aboard a Southern Wind at the Ibiza JoySail regatta. “I thought, ‘Boy, this is fun! All that teamwork.’ I was in my element.” The experience confirmed that her new boat had to race, as well as fit her lifestyle, be large enough for everyone to join should they wish, but not so large that their help is required. “Size was the most impor tant factor,” she says.

When Head laid eyes on Onyx II, built by a renowned Finnish shipyard that she is familiar with, it was a natural fit: “I sailed her and thought, ‘Yes, I could be at home on this boat.’ The crew accommodation is well done, the guest cabins are really nice and I liked the intimacy and sailability of her. I thought she was lovely.”

While the yacht’s attendance at the Rolex Swan Cup in Porto Cervo this September will only be a social visit, more regatta racing is certainly on the agenda. “The sailing world is a wonderful thing to be part of, everyone’s so welcoming,” she says. “For Corinthian Class sailing you don’t need a large crew, though you shouldn’t underestimate the prep work, but it’s so fun.”

Planned changes for the yacht include a new name – Arion, after the mythological Greek horse that could outrun the wind – and a new sewage treatment system, ahead of that coveted circumnavigation. Japan, Australia, New Zealand and French Polynesia are already earmarked, as is diving in Indonesia, and bluewater sailing in Cape Verde. “I guess I’ll be gone for a while,” she says.

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