HISTORY & HERITAGE

Some called him Captain Courageous; others, Captain Outrageous—and both were spot on. Ted Turner grew up sailing at the Savannah Yacht Club, and from age 12, he approached both sailing and life the same way: full-throttle.

Moving from dinghys to big boats, his dominance was sealed with a win in the 1966 Southern Ocean Racing Circuit. At the same time, he was building his media empire, a force that would disrupt American broadcasting as we know it.

Bold, controversial, and a true disruptor in his prime, Turner was a Renaissance man. Whether challenging the status quo of American television or throwing legendary après-sail celebrations, he always did things differently—with unmatched bravado and self-belief.

As Brad Siegal, a Turner Broadcasting executive, put it, “Whatever we did, he wanted to make sure it was something he’d be proud of because his name was on top.”

Turner always wanted more. So, in the 1970s, he turned to the America’s Cup. Coming in like a hurricane, he shook up the stagnant ways of the competition. Despite his rock-star attitude, Turner was fiercely loyal to his crew, recruiting teammates from the Southern Ocean Racing Circuit for the Cup. Ted Hood, in ’74, summed it up, “You certainly have to respect Ted Turner. He’s a competitor, and in his own way, he makes all of us work a bit harder.”

In 1977, Turner led Courageous to a 4-0 sweep against Australia. That same year, he claimed the Congressional Cup. Two years later, he triumphed in the storm-ravaged 1979 Fastnet Race.

Turner was a man of contradictions—pure enthusiasm mixed with sharp and relentless competitiveness. As a skipper, he was a firestorm—ranting, cursing, praising, excoriating—but also calculated and trusting. Off the water? No shortage of proof that Turner knew how to enjoy life. But make no mistake, victory was rarely optional.

Andrea Giuseppe “Beppe” Croce lived by two principles: duty and service. After his father was killed in World War I, he was raised in Nervi by his grandfather—also Beppe—in a household where sport and statesmanship were twin pillars. His grandfather, founder of the Italian Tennis Federation, hosted the Davis Cup in their garden. It was young Beppe who laid out the grass courts.

At nine, he was rewarded with a Dinghy 12’ for academic excellence. He began racing off the coast of Genoa and, by 1938, had won the Italian University Star Class Championship. During WWII, he fought as a liberal partisan officer. After the war, he became President of Lloyd Adriatico, the family insurance firm. Still, it was sailing that defined him.

When Yacht Club Italiano was nearly destroyed in 1944, Croce offered his home as its temporary headquarters. In 1948, he raced for Italy in the Olympic Games. In 1952, he co-founded the Giraglia Cup over dinner. A gentleman and strategist in equal measure, Croce went on to lead Yacht Club Italiano, the Italian Sailing Federation, and World Sailing (then the IYRU).

Under his leadership, the Naples Games ushered in a new era for Olympic sailing: sharper organization, refined courses, and a renewed commitment to Corinthian spirit.

From 1969 to his death in 1986 Beppe Croce was the first non-British President of the International Sailing Federation (ISAF), was President of the Italian Federation from 1957-81, and Vice-President of the Italian Olympic Committee 1973-78. 

Croce belonged to another era. He created regattas over dinner, hosted Portofino’s jet set with his wife, Countess Umberta Raggio, and quietly helped Gianni Agnelli and the Aga Khan VI plan Azzurra’s 1983 America’s Cup campaign.

To the very end, he held fast to his vision. Sailing, to Croce, was never just a sport—it was a vessel of diplomacy, a way to mend history and forge connection through shared tradition. His legacy lives on in the Beppe Croce Trophy, awarded by World Sailing to those who serve the sport not for profit, but for principle.

Unlike the yachtsmen of his era, Sir Thomas Lipton wasn’t raised with a silver spoon. He was the son of Irish immigrants, born in a Glasgow tenement. He left school at 10. Cabin boy at 15. After five years of hustle in the United States, he returned home and went straight to business.

On his 21st birthday, he opened a grocery shop. Twenty stores by 1881. Three hundred across Britain by 1890. Then came Lipton Tea: sealed, honestly weighed, and marketed with a cheeky touch. A five-ton cheese sent to Queen Victoria (politely declined, but the headlines landed). Soon everyone on both sides of the Atlantic knew his name.

Success earned a knighthood and a chair among aristocrats. It was time to chase another dream. Between 1899 and 1930, Lipton launched five Shamrocks in pursuit of the Auld Mug. Five campaigns. Five losses.

1920 brought the closest taste of victory. Shamrock IV took the first two races before Resolute shut the door. Lipton smiled, shook hands, and promised he would be back.

His final attempt came with Shamrock V. He commissioned Charles E. Nicholson to design the first J-Class to Herreshoff’s Universal Rule. Early promise in British waters. Refined with every race.

Then she reached Newport. A snapped halyard. A faster Enterprise. The Cup stayed home. Luck was not green that summer.

Lipton became known as “the people’s challenger” and the “lovable loser” — a masterclass in sportsmanship and stubborn optimism. After his final loss, he received a trophy engraved: “the best of all losers.” He is said to have cherished it most.

Vanderbilt remarked: “It has been our duty to shut the door in his face. In defeat lies the test of true sportsmanship, and he has proved to be a wonderful sportsman, quite the finest it has ever been our good fortune to race against.”

Lipton died a year later at 79, still without the Cup. But his legacy is unmistakable. Not bad for someone who never won.

Sometimes, the pursuit is the victory.

"So to all the yachtsman who are about to pit their yachts, skill, and endurance against the varying moods of the sea and against one another, Bon Voyage.” — Commodore A.B. Wilson of Cruising Yacht Club of Australia (1956)

In his opening letter for the 1956 racing program, Commodore Wilson signed off with a gentle reminder that these waters have never been accused of predictable behavior. It came down to nerve, judgment, and the willingness to accept whatever Mother Nature felt like delivering that year. Decades later,  following the 1998 race, Rob Mundle, shared a similar sentiment: “Mother Nature creates the rules and delivers the results.” 

Each Boxing Day, the Rolex Sydney Hobart Yacht Race kicks off in Sydney Harbour. Known as one of the toughest ocean races, competitors face the raw strength of the Bass Strait and the Pacific Ocean over the 630 nautical mile course. Sydney Harbour morphs into a theatre of spirited chaos—shorelines jammed with crowds, and spectator boats confidently occupying waters they absolutely should not be in. One harbour. One of the toughest ocean races. And one of the most festive amphitheatres ever to host an ocean-race start.

The race originated in 1945 as a cruise, organized by Peter Luke, co-founder of the Cruising Yacht Club of Australia. However, Royal Navy Officer Captain John Illingworth had other ideas. Illingworth listened, nodded, and asked the question that rearranged Australian summers: “Why don’t we race it?”  Illingworth won it. His boat, Rani, arrived in Hobart after 6 days, 14 hours, and 22 minutes. His fellow competitor, Luke finished last. He crossed the line after 11 days, 15 minutes, and 24 seconds— the longest recorded time to this day.

The top competitors strive to achieve the “Holy Grail” — finishing in under 40 hours. Nokia succeeded in 1999. LDV Comanche holds the current record, slicing through the course in 33 hours, 15 minutes, and 24 seconds in 2017.

Eighty years later, Illingworth's instinct still governs the day. The mythology is deserved. Some years deliver glory, others bring cautionary tales, and the Bass Strait always remains the Bass Strait.

In 1981, Yacht Club Costa Smeralda, co-founded by the Aga Khan IV  in 1967, launched the first Italian challenger for the America’s Cup. Azzurra was the brainchild of the Aga Khan and Gianni Agnelli. Designed by Andrea Vallicelli, the 12-meter was entirely Made in Italy.

When speaking about the Italian team, H.H. the Aga Khan stated, “We will face this breathtaking series of regattas with the humility of newcomers but with the conviction that we are worthy of participating.”

From the start, Azzurra faced resistance. Italian sailing wasn’t ready. Or so they were told. The country was in a period of rebuilding. The Cup committee wasn’t keen on newcomers.

They kept going.

Skipper Cino Ricci built his crew by placing an ad in Il Giornale della Vela. Athletes from across Italy—some seasoned, some total novices—showed up in Marina di Ravenna.

Still in need of a helmsman, Ricci tapped Olympic Finn sailor Mauro Pelaschier. With his wild blond beard and old-school grit, he was the unofficial face of Azzurra’s gamble. The Aga Khan presented the challenger on the final deadline in April 1981.

Classic Newport conditions. The first race? They won against France III. They fought their way to the semi-finals, winning 24 of 49 races.

Italy had arrived. And they weren’t done.

Four years later, YCCS returned— this time alongside a second Italian challenger, Yacht Club Italiano’s Italia.

Italy went on to win the Louis Vuitton Cup three times, earning the right to challenge the defender: Il Moro di Venezia in 1992, Luna Rossa in 2000 and 2021.

Azzurra’s 1983 debut—driven by passion, humility, and sheer will—transformed Italian sailing. For the first time, sailing stood alongside football and Formula One in the national psyche.

And the story isn’t over. For Azzurra’s 40th anniversary, Pianozero Media and journalist Stefano Vegliani produced “La Scia di un Sogno, a podcast chronicling the team’s rise.

Azzurra proved that Italian sailing was, in fact, ready.

Tracy Edwards was the only woman aboard Atlantic Privateer in the 1985–86 Whitbread Round the World Race. They made contact with Bertie Reed’s Stabilo Boss off of Cape Horn as he raced in the BOC single-handed Challenge.

Reed’s boat? The 58-foot Farr would later become Edwards’ Maiden.

Edwards didn’t just want to complete another Whitbread—she wanted to create the first all-female crew in its history. The general response? Skeptical at best, patronizing at worst.

To make it happen, Edwards remortgaged her home, secured funding from King Hussein of Jordan, and landed Royal Jordanian Airlines as a sponsor. Maiden arrived in Southampton with a dramatic dock after taking on water, but she was rebuilt from the keel to the mast.

In 1989, Maiden crossed the first startling line towards Uruguay. The 12-person crew finished third in their class—already defying expectations.

Leg 2: the brutal Southern Ocean crossing to Australia. Icebergs. Frostbite. Nine days sans satellite signal. During the journey, two sailors from Creightons Naturally fell overboard, with one, Anthony Phillips, unable to be revived. Aboard Maiden, Dr. Claire Russell remained on the radio for two days, providing guidance on how to keep the other man, Bart van den Dwey, alive.

Amid the challenges, Maiden powered on — arriving in Perth ten days ahead of its nearest competitor. Another victory followed in Leg 3, extending their lead to 28 hours overall.

Maiden embarked on its final leg back to Southampton, where they once again met the unforgiving forces of the Atlantic — surviving a tornado and the final five days without food. But they fought on, crossing the finish line victorious—winning two of the six legs and finishing second in class. The best British result in nearly two decades.

Tracy Edwards became the first woman to win the Yachtsman of the Year Award and was made a MBE.

Years later, Peter Travers of Rolling Stone summed it up perfectly: Maiden “knocked the sexist world on its ass.”

Il Moro di Venezia’s 1992 Louis Vuitton Cup victory, like any good story, had its fair share of twists and turns. In the late ‘80s, Raul Gardini wanted American Paul Cayard, a regular on nearly all of Gardini’s boats, to skipper his Italian challenger.

Slight issue. Cayard wasn’t Italian. According to the Deed of Gift, only an Italian could be at the helm.

When there’s a will, there’s a way. Enter a generous salary, a new Milan address, and by November 1988, Il Moro arrived in San Diego. Sorted. Andiamo.

The Cup has always been a stage for a bit of “yachting espionage”—be it heated protests or hidden keels—and the ’92 edition was no exception.

According to crew member Massimo Procopio, “we lived in an atmosphere of constant espionage in San Diego: helicopters would ply the skies to photograph opponents’ boats from above.”

Il Moro dominated the Round Robins but found itself down 3-1 going into the final series against Team New Zealand.

Enter those helicopter shots.

Il Moro’s photographer, Carlo Borlenghi, captured images of the Kiwis using their bowsprit as a spinnaker tack point. Rule violation. The Kiwis’ fourth point was tossed, and Il Moro claimed the LV Cup 5-3 on April 30, 1992.

However, from May 9-16, the defending America3, was faster, lighter, and better than Il Moro.

But the Italians had their moment. Dudi Coletti, a trimmer, recalls “even when we won that one race, at 1-1, we did it by just 3 seconds—thanks to Cayard’s genius decision to drop the spinnaker and let it fall forward at the finish.

“THIS LAND RESEMBLES NO OTHER PLACE.”

Sardinia—the island known for its legendary Mistral winds, strong enough to turn the narrow channels of the Maddalena Archipelago into a sailor’s paradise. Situated between Italy and France, Sardinia is a prime stop, with the north coast receiving the full force of the Mistral. The wind sweeps in from France, reaching speeds of 35 mph or more, while Porto Cervo’s thermal winds add a further challenge.

The island captivated English novelist D.H. Lawrence, who visited in 1921. In Sea and Sardinia, he described it as “savage, dark-bushed, sky-exposed land, forsaken to the sea and the sun” and remarked, “this land resembles no other place.”

For sailors, the sentiment rings just as true.


In 1967, Yacht Club Costa Smeralda was founded in Porto Cervo, quickly becoming a hub for Mediterranean and global offshore racing.

The club hosted The One Ton Cup in 1973, followed by creation of The Sardinia Cup in 1978, drawing sailors from all over. The 1980s saw the Maxi Yacht World Championship and the Swan World Cup, solidifying Sardinia’s place in yacht racing history.

The Sardinia Cup became Southern Europe’s answer to the Admiral’s Cup. Held in alternating years, it gave sailors a welcome break from the Solent.

In 2004, it was awarded the ISAF Offshore Team World Championship. The last edition, the Audi Sardinia Cup, took place in 2012. It is set to return to Porto Cervo in 2026.

“By building and sailing his own ships, and building and racing his own cars, he epitomized the definition of the American sportsman.”
— Sam Posey

Briggs Cunningham’s sporting legacy spanned two arenas few dared to master. By land, Le Mans. By sea, the America’s Cup. He was an amateur in name only. His standards matched, and often exceeded, the best.

Attending Yale, he studied engineering, played football, and met his future wife, Lucie Bedford, heiress to the Standard Oil fortune. He left after two years, but not before picking up a taste for yacht racing (thanks to Lucie) and a knack for mechanical design. Soon after, he was racing Star boats out of Pequot Yacht Club, joining Dorade for her 1931 Fastnet win, and later crewing for Harold Vanderbilt aboard Vim. He never lacked good boats or good company.

Following the Second World War, he purchased the US Coast Guard’s schooner Brilliant. Hoping to improve her speed, he modified the downhaul system. The Cunningham, as we know it, was born.

In parallel, he launched a motorsport empire. His eponymous Cunningham team fielded Cadillacs, Chryslers, Jaguars, and Maseratis. In 1952, he drove 20 of 24 hours nearly solo at Le Mans, finishing first in class and gaining near-mythical status in pit lane lore.

Then came his return to sailing’s highest stage: the America’s Cup. Cunningham joined the syndicate behind Columbia for the first post-war challenge in 1958. But when the original skipper, Cornelius “Corny” Shields was sidelined by illness, Briggs stepped up. Columbia dominated Sceptre. The press (along with everyone else) called it a demolition.

He retired from endurance racing in 1965 at the age of 58. One of his final appearances: the Sebring 12-Hour, where he quietly won his class. Not a bad way to exit.

Cunningham’s accolades were impressive. But it was his style—precise, restrained, and utterly unbothered by the spotlight—that left the real mark.

Saint-Tropez, September 1981.

Richard and Celia Jayson, an American couple, docked their Swan 44, Pride, after racing in Porto Cervo. Over lunch at Le Club 55, Patrice de Colmont — son of founder Bernard — chatted with Richard about his yacht.

Across the harbor sat Ikra, a sleek French 12M skippered by Patrice’s friend Jean Laurain. The Frenchman wondered aloud if Pride could beat Ikra. Richard, perhaps fueled by rosé and bravado, believed he could. Lunch ended with a simple agreement: “Why not, if Ikra accepts.” Laurain confirmed.

The terms were straightforward. The wager: Lunch at Le Club 55. Winner pays. The next day, Ikra easily bested Pride. With no trophy on hand, Patrice handed over a silver compotier from the French Navy. When a reporter asked what the race was called, Patrice didn’t hesitate: “Le Club 55 Cup.”

In 1982, Jayson returned looking for a rematch. Word spread. The next year, more boats appeared.

Something was missing: Maxis. As Alain Gouédard, a friend of de Colmont, remarked, “If there are no maxis, it’s not really a regatta.” Patrice agreed. One problem — no one in Saint-Tropez knew any Maxi owners.

Solution: Bluff.

A telex went to the Aga Khan in Porto Cervo: “The Yacht Club of Saint-Tropez (which didn’t exist) would like to present its regatta program to the Maxi owners. Could you arrange a meeting?”

It worked. A meeting was set.

Patrice flew to Sardinia armed with cigars, wine, and polo shirts stitched with a freshly minted Nioulargue crest. The skippers weren’t sold. He tried one last tactic: a surprise dockside breakfast for 200 people. Bellies full, curiosity piqued, the Maxis came to play.

The Nioulargue was born. No strict rules. No sponsors. Just racing, revelry, and Saint-Tropez magic.

In 1995, tragedy struck and racing paused. Four years later, under Thierry Catino and SNST, it returned as Les Voiles de Saint-Tropez. The spirit of the original regatta remains, even as it has grown into one of the world’s premier regattas.

Proof that a great lunch can get wildly out of hand.