On board the 34m sloop Kawil with owner Harold "Spook" Stream

Alongside his wanderlust, Stream admits a tendency to “make a competition out of almost everything”.

He is descended from a family that has been ranching in Louisiana since the mid-1800s, and this hunger for a challenge used to manifest itself in his success at cutting – a rodeo sport in which cowboys on nimble-footed Quarter Horses separate, or “cut”, an individual cattle from the herd and block it from returning by mirroring its movements.

A lifelong rider, Stream says his interest in horses “started with one gelding and years later wound up with 40 brood mares and some champion stallions”.

Today, Stream’s competitive streak is satiated on the regatta circuit. A year after he purchased Kawil, she came third in the Newport Bucket. In 2019, she went on to collect four straight wins at the Superyacht Challenge Antigua and won her class at the St Barths Bucket before collecting the winner’s trophy at the 2020 New Zealand Millennium Cup. In 2023, Kawil was again on the podium at the Superyacht Challenge Antigua.

As I joined Stream on board in Fiji to race in the South Pacific Superyacht Rendezvous last year, he was determined to add to his winning record. When the wind picked up in Nadi Bay, there was a gleam in his eye and a smile on his face. “Keep it up, we like double digits!” he encouraged his crew as we hit 10 knots.

Although on first impression he appears a reserved, southern gentleman, Stream’s enthusiasm on the racecourse is irrepressible. His love of sailing far predates his status as a superyacht owner, however. “I started sailing with my friends when I was six, in California. We took lessons on little Sabots at the Newport Harbour Yacht Club,” he reminisces.

Before buying Kawil, Stream had owned “powerboats, an offshore racer, a collection of wooden antique boats in New England… I worked my way up and the boats got bigger and bigger. I just love being on the water.” Stream first laid eyes on Kawil in Newport, Rhode Island. He recalls that he had “barely got into the saloon before I just had this feeling. I said ‘Damn, this is the boat.’ So we made a deal, bought the boat and immediately took her sailing.”

Launched from Derecktor Shipyards in 2000 as Zingaro, she attracted Stream with her “old gentleman’s sailing yacht feel”, which he so loves, admitting that his tastes are “still a little old-fashioned”. This retro design can be felt in the traditional teak panelling throughout her interiors and three staterooms, furnished with the occasional classic sailing painting.

But Stream doesn’t spend much time in the interior – he is happiest out on deck with just his girlfriend, Lori, and their Biewer terrier, Juju.

“I don’t entertain a lot on board, so Kawil is plenty of boat for me. I don’t want a boat where I have to worry about having five staterooms full of people, and dealing with more than five or six crew members. Kawil is not big in terms of today’s boats, but she is a very comfortable size for me.”

Of greater priority to Stream than hosting is Kawil’s sailing performance, which can see her reach speeds of 14 knots. “North Sails have spent a lot of time with us, helping us perfect our sails for cruising and racing. And we’ve been very fortunate to find a great race crew,” Stream explains. He admits, “I didn’t think that I would keep her quite as long as I have. But she is just such a great sailing platform.”

When Stream isn’t sailing, he’s diving – a hobby he’s enjoyed for more than 45 years. Kawil has been decked out accordingly, fully equipped with Scubapro and Aqualung gear on board.

“One of the reasons we keep coming back to the South Pacific is for the diving. We do a lot of shark diving and some of the best has been here in Fiji.

“If you’re a diver, you also have to go to Vanuatu. Espiritu Santo is amazing because they have so much stuff sunken in the water there, like the SS Calvin Coolidge and Million Dollar Point. And anyone who can get on a mask and flippers has to swim with whales.”

Deep-sea diving is not the only activity that lures Stream back to the South Pacific time and again. He mentions watching the land diving in Vanuatu and unwinding on the French Polynesian island of Huahine-Iti as some of his travel highlights.

Stream also has a soft spot for New Zealand, where he talks of sailing in the Bay of Islands, road-tripping around South Island and tasting wines at Stonyridge and Cloudy Bay vineyards. “I was never such a Sauvignon Blanc fan before then,” he chuckles.

Of all the regions that Stream has visited with Kawil, the South Pacific remains his favourite. “I’ve been visiting Europe since I was 10 years old, but actually, I’m not a fan of the Med,” he says. “On the Riviera, people like to spend a lot of time ashore, having drinks with their buddies and eating at the famous restaurants… but we don’t want to worry about all that.”

Stream prefers the seclusion of the South Seas instead. “The South Pacific can be challenging at times, especially provisioning. But we love the solitude, we love the sailing, we love the adventure,” explains Stream. “It’s a long way to come, so you really have to want to be here.”

Referring to his 24-year-old captain, Stream shares that he also finds joy in helping youngsters gain experience outside of common cruising grounds: “I’ve started several captains on Kawil – we don’t do the normal ‘milk runs’, so it’s a great opportunity for them to cut their teeth.”

When on land, Stream is usually in the US or Mexico. Home is in Idaho’s Sun Valley, where he used to spend Christmas with his parents. “My mother was there when the ski resort opened in 1936 and she went every year, except when they closed during the Second World War. She skied there until her 80s.” He remembers his mother with great fondness and shares riotous stories of her travels, describing her as an intrepid explorer.

“I don’t want to sound like we’re on a Star Trek mission, but we like to go where nobody else is”

In Mexico, Stream keeps an homage to his mother in the form of Hotel Matilda; a 32-bedroom boutique in San Miguel de Allende. It is the last in a portfolio of hotels and properties that Stream used to own, as a “hobby”, which began with the purchase of the Warwick hotel in Houston in the 1970s when he was in his early 20s. The hotel honours both Stream’s mother and his great-aunt, who shared a name and also a similar talent for generating “lots of crazy family stories”.

The connection to South America begins with the first Matilda, he explains: “The family had a number of coffee fincas in the mountains of Guatemala and my great-aunt loved spending time in Guatemala, Mexico and Antigua.”

He describes her as “quite a character”, always in Chanel suits and pillbox hats, who “seemed to run around with everyone in the world”; she was painted by Diego Rivera, was friends with Frida Kahlo and learned to water ski in Acapulco with Errol Flynn.

Stream’s continuing affinity for South America is also what gave Kawil her name – inspired by the Maya god of lightning. Although Stream’s family “was never into boats”, what he did inherit from them were their passions for travelling and art.

“My parents always said that travel is the best form of education. So I started travelling from around four years old. And I would get dragged around three museums a day,” he recounts.

Stream reckons he has been adding artworks to the family collection for more than four decades now. He has a particular penchant for contemporary and Latin art, owning pieces by Diego Rivera, Damien Hirst, Tracey Emin and Jason Martin.

He reveals that “most of the family collections have been at the Metropolitan Museum of Art in New York for about 10 years now, including a very large collection of Fabergé jewellery and Imperial Easter Eggs.” When asked how many artworks Stream owns, he answers “I’m not trying to be glib, but I really have no idea now. Several hundred probably.”

The first day of racing on Kawil ended in triumph. With determination and some decent winds she slipped first over the finish line, amid creaking lines and salty sea spray. The crew, owner and guests finished the day with a bottle of champagne under the setting South Pacific sun.

Kawil may not have gone home with the overall trophy from the South Pacific Superyacht Rendezvous, but that’s likely motivation for Stream to return in August 2025 to challenge this year’s winner – the Oyster 72 Crazy Horse.

Until then, Stream will venture to New Zealand in preparation for the 2025 Millennium Cup. After that he is setting his sights on Asia, planning visits to Indonesia, Malaysia and Japan. Kawil is just the partner for the job, as he calls her “a go-anywhere-in-the-world kind of boat”.

Before I disembarked, there’s one more question I had to ask Stream: the origin of his nickname “Spook” – to which he gave a simple answer – his birthday is on Halloween.