by Ryan Craig
Great Lakes Bike Ski Boat
Sailing has always attracted a certain kind of person. It requires patience, independence, and a willingness to face the unpredictable power of the sea. Over the years, some very famous people have fallen deeply in love with sailing—actors, musicians, billionaires, kings, and even presidents.
For many of them, sailing wasn’t just a hobby. It was a passion that shaped their lives, gave them peace away from fame, and sometimes even brought them international recognition. Here are 15 well-known celebrities who loved life under sail.
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Ted Turner
Ted Turner is best known as the founder of CNN and one of the most influential media entrepreneurs in American history. He built a broadcasting empire that transformed television news and created networks like TBS and TNT. Turner also became famous for his outspoken personality, environmental activism, and enormous land holdings across the United States. By the 1970s and 80s he was widely recognized as one of the most powerful and colorful figures in American media.
But long before he became a media titan, Turner was obsessed with sailing. He was an extremely competitive sailor and one of the most accomplished amateur racers of his era. In 1977, Turner skippered the yacht Courageous to victory in the America’s Cup, the most prestigious sailing race in the world. He was known for his aggressive racing style and intense dedication to the sport. Turner often said sailing taught him the discipline and competitiveness that later helped him succeed in business.
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Simon Le Bon
Simon Le Bon rose to fame as the lead singer of the legendary 1980s band Duran Duran. With hits like Hungry Like the Wolf, Rio, and Ordinary World, the band became one of the defining acts of the MTV era. Le Bon’s charismatic stage presence and distinctive voice helped make Duran Duran a global sensation.
Le Bon is also an experienced sailor who once competed in the Whitbread Round the World Race, one of the toughest sailing competitions on Earth. In 1985 he sailed aboard the yacht Drum, which famously capsized during the race. Le Bon survived the dramatic accident and continued his involvement with sailing afterward. His participation showed that his love of the sea was far more than a celebrity hobby.
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Larry Ellison
Larry Ellison is the co-founder of Oracle Corporation and one of the richest people in the world. As a technology pioneer, he helped build Oracle into one of the most powerful software companies in the global tech industry. Ellison is known for his bold personality, competitive nature, and lavish lifestyle, including luxury homes, private jets, and the Hawaiian island of Lanai, which he purchased in 2012.
Ellison’s true passion, however, may be sailing. He has invested enormous resources into competitive sailing and became deeply involved in the America’s Cup. Through his team, Oracle Team USA, Ellison funded cutting-edge racing yachts and helped revolutionize modern yacht racing with high-tech foiling catamarans. Under his leadership, Oracle Team USA famously staged one of the greatest comebacks in sports history during the 2013 America’s Cup, turning a massive deficit into victory.
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John F. Kennedy
John F. Kennedy, the 35th President of the United States, remains one of the most admired political figures in American history. Before becoming president, he served in the U.S. Navy during World War II and later represented Massachusetts in Congress and the Senate. His presidency is remembered for the Cuban Missile Crisis, the early years of the space race, and his powerful call for public service.
Kennedy’s love of sailing began during his childhood summers in Hyannis Port, Massachusetts, where the Kennedy family spent time on the water. He frequently sailed small boats with his siblings and developed a lifelong appreciation for the sea. Even during his presidency, Kennedy often escaped to the water whenever possible, finding sailing to be one of the few activities where he could truly relax. For JFK, the ocean was both a refuge and a reminder of his family’s New England roots.
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Sir Thomas Lipton
Sir Thomas Lipton was a Scottish businessman who became famous for building the Lipton Tea Company into a global brand. In the late 19th and early 20th centuries, Lipton revolutionized the tea industry by creating affordable packaged tea for everyday consumers. His marketing genius and entrepreneurial spirit made him one of the most recognizable businessmen of his era.
Lipton was also one of the most passionate sailing enthusiasts in history. He challenged for the America’s Cup five times between 1899 and 1930 with a series of yachts named Shamrock. Although he never won the trophy, his sportsmanship and enthusiasm made him hugely popular with sailing fans around the world. Lipton became a beloved figure in yacht racing, and his determination helped popularize international competitive sailing.
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Humphrey Bogart
Humphrey Bogart was one of Hollywood’s most legendary actors during the Golden Age of cinema. Known for his tough yet charismatic persona, Bogart starred in classic films like Casablanca, The Maltese Falcon, and The African Queen. His performances helped define the film noir genre, and his cool, understated style made him a cultural icon.
In his personal life, Bogart loved boating and sailing along the California coast. He owned several boats and spent much of his free time on the water with friends and fellow actors. His yacht, the Santana, became famous among Hollywood circles as a gathering place for celebrities who shared his love of the sea. For Bogart, sailing offered freedom and adventure far removed from the movie studios.
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King Constantine II of Greece
King Constantine II served as the last King of Greece before the monarchy was abolished in 1973. Before entering political life, he gained international recognition as an athlete. Constantine competed in sailing and won a gold medal in the 1960 Olympics in the Dragon class.
Sailing remained a lifelong passion for Constantine. Even after political upheaval forced him into exile, he continued to stay connected to the sailing world. His Olympic victory remains one of the most famous achievements by a royal athlete and helped inspire many sailors across Europe.
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King Juan Carlos I
King Juan Carlos I of Spain played a major role in shaping modern Spanish history. After the death of dictator Francisco Franco in 1975, he guided Spain through a peaceful transition to a democratic constitutional monarchy. His leadership during this period earned international respect, particularly when he helped defend democracy during the attempted military coup of 1981.
Juan Carlos has also been a lifelong sailing enthusiast and competitive yachtsman. He competed as a member of Spain’s sailing team in the 1972 Munich Olympics and later raced in many international regattas, often aboard yachts named Bribón. His passion for sailing helped raise the sport’s profile in Spain and influenced a new generation of Spanish sailors, including his son, King Felipe VI.
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Pete Townshend
Pete Townshend is best known as the guitarist and primary songwriter for the legendary rock band The Who. His music helped shape rock history with albums such as Tommy, Who’s Next, and Quadrophenia. Townshend’s powerful guitar playing and songwriting helped define the sound of classic rock.
Away from the stage, Townshend has long enjoyed sailing as a personal escape from the intense world of music. He has spoken about how the solitude of the sea allows him to think creatively and relax away from the pressures of touring and recording. Like many musicians, Townshend finds sailing to be a meditative experience where the rhythm of wind and waves replaces the noise of fame.
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Jimmy Buffett
Jimmy Buffett was a singer, songwriter, and entrepreneur best known for creating the laid-back musical world of “Margaritaville.” His music celebrated beach life, sailing, and tropical escapes, earning him a loyal fan base known as “Parrotheads.” Buffett turned his lifestyle brand into restaurants, resorts, and a global entertainment empire.
Sailing and boating were central themes throughout Buffett’s life and music. He spent much of his time on boats exploring the Caribbean and Gulf Coast waters. Many of his songs reference life at sea, harbors, and island adventures. For Buffett, sailing wasn’t just recreation—it was the inspiration behind an entire cultural movement built around freedom and coastal living.
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Sterling Hayden
Sterling Hayden was a Hollywood actor known for roles in films such as The Godfather, Dr. Strangelove, and The Asphalt Jungle. With his rugged appearance and commanding voice, Hayden often portrayed tough characters and authority figures. He also served in the U.S. Marines and worked with the OSS during World War II.
But Hayden’s true passion was sailing. He owned several boats and spent years sailing around the world, often disappearing from Hollywood to pursue life at sea. He once said he regretted the years he spent acting because they kept him away from sailing. His autobiography, Wanderer, describes his adventures crossing oceans and living the sailor’s life.
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Errol Flynn
Errol Flynn was one of the biggest movie stars of the 1930s and 1940s, famous for swashbuckling adventure films like The Adventures of Robin Hood and Captain Blood. His charm, daring on-screen roles, and flamboyant lifestyle made him one of Hollywood’s most famous leading men.
Flynn’s adventurous spirit extended beyond film sets and onto the ocean. He owned several yachts and spent years sailing through the Caribbean and the Pacific. Flynn loved exploring remote islands and living the romantic life of a sailor. His time at sea became part of the legend surrounding his larger-than-life personality.
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Harold Stirling Vanderbilt
Harold Stirling Vanderbilt was a member of the wealthy Vanderbilt family and a prominent businessman and philanthropist. While the Vanderbilt name was already famous due to railroad and shipping fortunes, Harold made his own mark in finance and international business.
He was also one of the greatest sailors of the early 20th century. Vanderbilt won the America’s Cup three times as skipper in 1930, 1934, and 1937. He was known for his strategic brilliance and calm leadership during races. Vanderbilt also developed the modern system of contract bridge scoring, proving his talent for both sailing and intellectual games.
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Morgan Freeman
Morgan Freeman is one of the most respected actors in Hollywood history. Known for his distinctive voice and calm presence, Freeman has starred in legendary films such as The Shawshank Redemption, Driving Miss Daisy, Million Dollar Baby, and Se7en. His career spans more than five decades and includes Academy Awards, Golden Globes, and countless iconic performances that have made him one of the most recognizable figures in film.
Away from movie sets and red carpets, Freeman has long enjoyed sailing as a way to escape the pressures of fame. He has owned and sailed several boats over the years and often speaks about how peaceful life on the water feels compared to Hollywood. For Freeman, sailing is about quiet reflection, freedom, and reconnecting with nature. Like many sailors, he appreciates the simplicity of navigating wind and water after spending so much time in the complex world of filmmaking.
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Bob Seger
Bob Seger is an American rock singer, songwriter, and musician best known for his powerful voice and heartland rock sound. Rising to fame in the 1970s with the Silver Bullet Band, Seger produced a string of classic hits including Night Moves, Old Time Rock and Roll, Against the Wind, and Turn the Page. His music often focused on working-class life, nostalgia, and the experiences of everyday Americans, which helped him build a loyal fan base across generations. Seger was inducted into the Rock and Roll Hall of Fame in 2004, cementing his place as one of the most influential rock musicians of his era.
Seger has long had a deep connection to the water, particularly in his home state of Michigan where the Great Lakes boating culture runs strong. He has owned boats and spent many summers enjoying time on the water around Detroit and the Lake Michigan shoreline including participating in Mackinac Island races. Like many sailors and boaters from the region, Seger appreciated the freedom and quiet that life on the water provides. For him, boating and sailing offered a welcome escape from the pressures of touring and performing, allowing him to unwind and reconnect with the same Midwestern landscapes that inspired much of his music.
Sailing has a unique way of drawing people in, no matter how famous or powerful they may be. From presidents and kings to rock stars and Hollywood legends, the sea offers something that money and fame cannot—freedom, challenge, and a sense of adventure that has inspired sailors for centuries. Whether racing for the America’s Cup, cruising quiet coastal waters, or simply escaping the spotlight for a few peaceful hours under sail, these celebrities found the same thing countless sailors discover: life just feels better when the wind fills the sails.
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