RUM AND RACING

But the concept of fun racing for big sailing boats goes further back – to the island of Nantucket in 1986. It was the eve of Nelson Doubleday’s birthday – the genial owner of the 28-metre sloop Mandalay – and his captain John Clyde-Smith was looking for a way to enliven the big day.

Over what he described afterwards as a “torrid rum squall”, he and two other superyacht captains put their heads together to devise a 15-nautical-mile course around Nantucket Sound. Seven yachts turned out, and the occasion passed into yachting folklore.

The principles that came to define the Nantucket event in subsequent years were transferred wholesale to St Barths: informal, social and fun. Two of the Caribbean event’s founders were part of a familiar crowd from Nantucket. Clyde-Smith was there with Doubleday’s latest incarnation of Mandalay – by then a 40-metre Palmer-Johnson ketch; Tom Taylor’s Gleam was involved, as well as Sariyah, a 40-metre Sparkman & Stephens ketch owned by a character known as “the Sheikh”.

Yachts were invited to join and loosely rated for staggered starts. This pursuit model – with slower boats setting off first and faster ones speeding to overtake them – generated some thrilling action on the course, as well as neck-and-neck finishes.

“Crossing situations were awe-inspiring, a sight that few had experienced, ever,” recalls Hank Halsted, a crew fixture and organiser who later came in as the event’s managing director.

Trophies were awarded to each yacht, although not usually for winning. Among the most coveted was the Escargot Cup, handed to the boat that placed last. “Fishing was a big part of the first races around St. Barths, with Gleam the usual winner in that department,” says Laughridge. “And the stated aim was to win the party.”

With relatively few boats at first and a laidback Corinthian atmosphere, the early rating system was a matter for good-natured joshing and even some outright skullduggery. “The yearly tongue-in-cheek solicitations by the race committee of bribes for better ratings illustrate the spirit of the event,” says ratings guru Jim Teeters, now at US Sailing. “Champagne flowed to the handicappers more as sacrificial offerings than as real expectations of a better start time for the races.”

“The engine prestart safety had devolved into a pedal-to-the-metal blue smoke diesel drag race to the line, which was more dangerous”
- Hank Halsted

A mix of observation, rational guesswork and a bit of humour lay behind each handicap, which could change from race to race, according to Halsted. “No yacht was permitted to win – or lose – more than once; rating changes assured that. If you earned the Escargot Cup, your rating was adjusted to prevent a recurrence.”

That started to change in the mid-2000s, as more boats joined, and a more scientific Bucket Rule began to evolve. In 2004, the fleet doubled in size to 20, and the following year, with festivities expanded to fill three days, it reached 28 boats.

Light winds that year and the next kept the focus firmly on the social agenda, although the race committee did their best. The 2006 Bucket saw 90 starts and zero finishes – surely a record for a high-end regatta.

Up to this point, competitors had been encouraged to motor to the start line to improve manoeuvrability, but in 2006 they returned to more proper sailing starts. “In practice, the engine pre-start safety had devolved into a pedal-to-the-metal blue smoke diesel drag race to the line, which was more dangerous,” Halsted says.

Laughridge stepped back, recognising that a dedicated events team was also needed to keep things on track. “The professionals were getting too aggressive, justifying their salaries and winning the regatta by protest,” he says. “It has plateaued now, and the event stewards are doing a good job of trying to keep it Corinthian with a separate J Class, non-spinnaker classes and so on.”

“Fishing was a big part of the first races around St Barths, with Gleam the usual winner in that department. And the stated aim was to win the party”
- Tim Laughridge

He tells the story of one pushy owner who pursued him halfway around the world to ask why he hadn’t been invited back. “His behaviour wasn’t acceptable, but he apologised by offering to supply the band, and he’s taken part ever since.”

The parties associated with the Bucket are legendary, of course. The late Jimmy Buffett with his Coral Reefer Band was a stalwart supporter, but many crew and owners have also stepped up to the mike. The Yacht Hop is an eagerly awaited fixture, where a troop of increasingly giddy Bucketeers jump from one vessel to the next, each hosting their own themed bashes.

Former Bucket blogger Norma Trease singles out Hap Fauth’s 35-metre sloop Whisper for commitment to the fun side of the Bucket. “From their signature tees ‘Got Wind?’ or ‘Bucket Love’ to fully kitted uniforms , even including ‘ Giddy Up ! ’ underwear,” she remembers. “My personal favourite was the Green Flash party, complete with green frozen drinks, and an eerie light effect which truly lit up the party. We all saw green flashes that night – long after the sun set!”

Dressing up is a big part of St Barths partying today – from good-luck socks on Lord Bamford’s Rosehearty to flares on Rebecca or cheerleading outfits on Perseus 3. But the highlight for many is the crew party hosted by the Bucket Committee at Nikki Beach or La Plage. “No Bucket is ever truly over until the after-party is finished,” Trease says.

“Champagne flowed to the handicappers more as sacrificial offerings than as real expectations of a better start times for the races”
- Jim Teeters

There is a more serious side to the Bucket, too. It constitutes the island’s second-busiest week after Christmas, pulling in thousands of crew, guests and visitors as well as thousands of bottles of champagne. There are financial supporters, although you’d be forgiven for not spotting them. Vitters, Royal Huisman, Pendennis, Perini Navi, Baltic Yachts and Nautor Swan yachts constitute much of the regular fleet.

These builders, and a number of other companies, support the event in exchange for low-key networking opportunities with the world’s wealthiest yacht owners and other players in the superyacht sailing industry.

And perhaps most importantly, €500 of each entry fee plus proceeds from poster sales go into a fund that invests in social benefits for the island – from church roof repairs to 2024’s robotic buoy for the yacht club’s youth sailing programme.

Despite all the high jinks and highballs down the years, it is this that Laughridge remembers most fondly. “The greatest pleasure was the contribution each year of the charity of choice, giving back to the people of St Barths, who always supported us with open arms and love.”

First published in the March 2025 issue of BOAT International. Get this magazine sent straight to your door, or subscribe and never miss an issue.