Famous People Who Sail(ed)

Seeing Morgan Freeman on the cover of Cruising Outpost  made me revisit the topic of famous people who love or have loved sailing. From actors to politicians, rock stars to physicists, sailing has attracted some interesting characters, perhaps giving sailing the illusion that you have to be rich to sail. I've been collecting images for some time, so I'm going to put them together here as a record of sailing's colorful and well known characters. It's about famous people who took up sailing. I have a separate page about accomplished Women Sailors. Come back from time to time to see who I've added.

Movie/TV Stars

Jude Law and Giancarlo Giannini

Daniel Craig (007, Bond, James Bond)

Spotted in Jamaica 2019 while preparing to film the 25th James Bond movie back where it all started. Ian Fleming wrote the Bond books at Golden Eye, the house he lived in in Jamaica. 

Daniel Craig begins filming as 007 for last time as Bond 25 kicks off in Jamaica Emma KellyWednesday 1 May 2019 1:12 pm Share this article via facebookShare this article via twitterShare this article via messenger 122 SHARES Daniel was living the dream (Picture: Splash News) Bond 25 has begun filming – and life looks pretty cushy for Daniel Craig. The 51-year-old was pictured out on a sailing boat in Jamaica filming the upcoming, as-yet-untitled James Bond film, and honestly, we don’t know why he’d ever give up this job. Daniel, dressed in a grey t-shirt and sunglasses, was seen out at sea in the custom built Spirit Yachts sailing boat, which was flying the Union Jack. Well, he is part of Her Majesty’s Secret Service, after all. While Daniel sailed ‘solo’, his stunt double Jean-Charles Rousseau was pictured standing by on the dock in a rather fetching pink shirt. This is believed to be Daniel’s last outing as 007 (Picture: Splash News) Jean-Charles Rousseau is Craig’s dashing stunt double (Picture: Splash) We didn’t see any stunts taking place which would give any clues about the plot, but then again, it’s only day two of filming. Bond 25 is beginning its filming on location in Jamaica, before heading to London, Italy and Norway; production will also take place at Pinewood Studios. Producers Barbara Broccoli and Michael G Wilson said: ‘We’re thrilled to return to Jamaica with Bond 25, Daniel Craig’s fifth instalment in the 007 series, where Ian Fleming created the iconic James Bond character and Dr No and Live And Let Die were filmed.’ While the film hasn’t got a title yet, we have got a basic plot outline: ‘Bond has left active service and is enjoying a tranquil life in Jamaica.  His peace is short-lived when his old friend Felix Leiter from the CIA turns up asking for help. Bond is enjoying civilian life in Jamaica (Picture: Splash News) It’s believed the script hasn’t been completed (Picture: Splash News) ‘The mission to rescue a kidnapped scientist turns out to be far more treacherous than expected, leading Bond onto the trail of a mysterious villain armed with dangerous new technology.’ The mysterious villain is likely Rami Malek, after the Mr Robot and Bohemian Rhapsody star was confirmed to be joining the cast. Daniel admitted he’s already scared of going up against Malek, who said: ‘I’m very much looking forward to joining the cast and crew so very soon. And I promise you all I will be making sure Mr Bond does not have an easy ride of it in this, his 25th outing.’ Captain Marvel’s Lashana Lynch has also joined the cast alongside Billy Magnussen, David Dencik, Dali Benssalah and Ana de Armas, while Ralph Fiennes, Naomie Harris, Lea Seydoux, Ben Whishaw and Jeffrey Wright will all be back for more. MORE: JAMES BOND Rami Malek 'to be killed off in grisliest death' in 007 history as actor plays villain Bond 25 'nowhere close to beginning filming' as Daniel Craig is 'making things impossible' Phoebe Waller-Bridge's career: From Fleabag to James Bond 25 James Bond producer Barbara Broccoli shuts down ‘gimmicky’ hopes for female Bond Cary Joji Fukunaga will direct, while Fleabag’s Phoebe Waller-Bridge has joined as a writer alongside Neal Purvis, Robert Wade and Scott Z Burns. However, while things looked like smooth sailing, literally, as Daniel began filming, insiders have claimed the script only has a beginning thus far. ‘They rolled out the cast this week at Ian Fleming’s villa in Jamaica because if they wait much longer Daniel Craig, who is 51, will be too old, and then he really won’t do the film,’ the source alleged to Page Six. ‘He’s so difficult and makes things impossible. But Barbara Broccoli thinks he walks on water, and only her opinion matters.’ Bond 25 is set for release on 3 April 2020.

Read more: https://metro.co.uk/2019/05/01/daniel-craig-begins-filming-last-outing-007-bond-25-kicks-off-jamaica-9375304/?ito=cbshare
Twitter: https://twitter.com/MetroUK | Facebook: https://www.facebook.com/MetroUK/

Morgan Freeman

Morgan Freeman, who has been sailing since 1967, is passionate about cruising. I'd love to meet him. He is currently Honorary Advisory Board Chair of the National Sailing Hall of Fame in Annapolis. He took over that post from Walter Cronkite. Freeman keeps a boat

Freeman has appeared in such critical and box office smashes as “Glory”, “Driving Miss Daisy”, “Unforgiven”, “Shawshank Redemption”, “Invictus” and “Seven” and won an Oscar for “Million Dollar Baby.” But in 1979 Freeman was still struggling to make a name for himself. When he and his wife left Bermuda aboard their small yacht en route for New York, they encountered a heavy storm that resulted in a knockdown. He briefly considered calling Mayday but decided instead to take control himself. He managed to right the yacht and sailed to New York through a snowstorm, the first time it snowed in New York in October in a hundred years. He credits this voyage as shaping his character and the rest of his life.

Known as “Captain Morgan” in sailing circles, Freeman has returned to Bermuda a number of times, including during the summer of 1989 when he sailed there aboard his Shannon 38, Sojourner. In the 1990s he cruised to the Caribbean and was so enchanted he lived part-time in the Grenadines for five years.

In 2004, after Hurricane Ivan ravaged the island of Grenada, Freeman established the Grenada Relief Fund and in 2005 published a lavish charity cookbook which brought together celebrities to benefit that island. Morgan Freeman and Friends: Caribbean Cooking for a Cause featured then Bermuda resident Michael Douglas, Tom Hanks and Alicia Keys, who shared their favorite island recipes and told anecdotes about what island living means to them.

Errol Flynn

Errol Flynn found fame with his portrayals of swashbuckling heroes such as The Adventures of Robin Hood, Captain Blood and Sea Hawk, yet his real life was even more adventurous than any of his films. According to stories I have heard told by residents of Jamaica, the famous (or infamous) actor had a swashbuckling persona both on land & sea and in film. He once was reported to wreck a sailboat on the island. The serial womanising, heavy-drinking, drug-taking hedonistic hellraiser packed more into his 50 years than most would do in several lifetimes.

Born in Hobart, Tasmania, Flynn worked as a tobacco farmer and gold prospector in New Guinea before fleeing after being accused of murdering a native. Despite Flynn's claims of having descended from  Bounty mutineers, the evidence indicates that he was not. Both of his parents were native-born Australians of Irish, English, and Scottish descent. He dodged bullets and bombs as a reporter in the Spanish Civil War and there were allegations that he was a Nazi spy; he was a skilled yachtsman; he relished brawling; he was a drinking partner of Fidel Castro; and a member of the Hollywood Cricket Club along with David Niven. Yet it is for his sexual exploits and bisexual appetite that he is most remembered. He was tried and acquitted of statutory rape. 

There are several stories how Errol acquired the Sirocco in 1938, The John Alden 75' classic wooden ketch was launched in 1929 as Karenita and Flynn renamed her after the first Sirocco.  One story suggests his mother purchased her, one says his father purchased her. Errol said he won her in a card game. Whatever the story, he sailed her to New Guinea through the Great Barrier Reef in 1930. 

Flynn retired to Jamaica to write his autobiography My Wicked Wicked Ways. He died of a heart attack in October 1959 just four months after his 50th birthday. True to form he was buried with six bottles of whisky in his coffin. 

Sterling Hayden

Sterling Hayden was a popular actor in Hollywood. He was born in Upper Montclair NJ, but was adopted after his father died and lived in many coastal New England towns. He dropped out of school at 16, and took up a career of sailing and fishing aboard schooners and steamers. He acquired a Master's license and was awarded his first command at the age of 22 in 1938. He was 6 feet 5 inches tall and handsome, which caused him to be recruited into modelling and then acting. 

After making two movies, he enlisted in the US Marine Corps and was recommended for Officer Candidate School. After graduating, he became an undercover agent for the agency that was to become the OSS. He received a Silver Star and other awards for his bravery. He retired from active service in 1945, after which he returned to acting.

For most of his career as a leading man, he specialized in westerns and film noir, such as Johnny Guitar, The Asphalt Jungle, and The Killing. Later on he became noted for appearing in supporting roles such as Gen. Jack D. Ripper in Dr. Strangelove (1964). He also played the Irish American policeman Captain McCluskey in The Godfather in 1972 and the novelist Roger Wade in 1973's The Long Goodbye. He played the role of Leo Dalcò in Bernardo Bertolucci's 1900 in 1976. He often professed a disdain for acting as a career, citing the reason for doing so as to secure funding for his boating and traveling passions. 
After a bitter divorce from Betty Ann de Noon, he defied a court order and took his four children sailing aboard his schooner, Wanderer. The crew sailed from San Francisco to Tahiti, planning to make a film, which never did materialize. In the early 1960s, Hayden rented one of the pilot houses of the retired ferryboat Berkeley, docked in Sausalito, California, where he resided while writing his autobiography Wanderer, which was first published in 1963. Wanderer was beautifully written and examines all the turning points in his life. I have a treasured copy in my library. It was followed by an acclaimed novel, Voyage (1976). Hayden married a second time and had two more children. He remained married to Catherine Devine McConnell, an heir to the Avon fortune, until his death from prostate cancer in 1986 at the age of 70. What an extraordinary life. 

Bogie and Bacall

Clark Gable

Cliff Robertson & Angie Dickinson

Audrey Hepburn

Natalie Wood

Walter Cronkite

Jeremy Irons

Jeremy Irons restored Kilcoe Castle and sails the Willing Lass in Roaringwater Bay. 

Christopher Reeve

Christopher Reeve, better known as Superman before an accident left him paraplegic, was an enthusiastic sailor and a veteran of several blue water crossings from the East Coast to Bermuda. Gary Jobson sailing with Christopher aboard his Cambria 46.

George Clooney (more of a power yacht person)


Grace Kelly

Queen Elizabeth II while still Princess Elizabeth with Prince Philip

Princess Anne, Daughter of Queen Elizabeth II


Former King Juan Carlos of Spain


King Harold of Norway



Sir Paul McCartney

Still fab at seventy-eight

Published on August 22nd, 2020

Beatles singer, Paul McCartney, 78, showing his Sunfish skill on August 22. For more photos, click here.

John Lennon

Simon Le Bon

Neil Young

Canadian native Neil Young cruised his 101-foot Baltic trading schooner, W.N. Ragland, far and wide. In the late 1960s, singer-songwriter Neil Young disbanded Buffalo Springfield, the rock group he had formed with Stephen Stills, and joined a fledgling group called Crosby, Stills & Nash to form the legendary Crosby, Stills, Nash & Young. History was made at Woodstock and Neil Young went on to have an illustrious solo career.

According to the brokerage listing from 2010 when Ragland came up for sale, "Built in 1913, W.N. Ragland is a two-masted, gaff-rigged schooner owned by Young for more than 35 years. Originally built of oak and used to haul granite, Ragland is outfitted with a railroad car full of mahogany in her hull. The ship features solid teak decks and deck structures up to four inches thick. Her standing rigging is all stainless steel. Yacht braid rope is used for her running rigging and lines, as opposed to the more common triple-strand line."

The sea had always drawn Neil Young, and he wrote songs about it. It was no surprise that with his newfound wealth he acquired a most unusual yacht. At a time when rock musicians were more likely to be partying aboard large motoryachts, Young chose a rustic trading schooner.

Jimmy Buffet

Richard Wright from Pink Floyd

Pete Townshend of The Who

Aboard Gloria with Pete Townshend


John F. Kennedy

Robert Kennedy

Fidel Castro

Okay, so he's fishing not sailing.

Sir Edward Heath



Governor Andrew Cuomo

Scuttlebutt named Andrew Cuomo the sailing governor. He was married to a Kennedy. 

Cuomo even issued a nautical themed vision for 2020 for New York State. 


Ted Turner

Many people are not aware that CNN Founder Ted Turner won the America's Cup in 1977 aboard Courageous, the first aluminum 12-Meter. He was a maverick, somewhat unconventional, loud-mouthed sailor and the establishment didn't want him to defend the Cup. But he had a spark, loved being an underdog and  had a passion for winning. Here he is on the cover of Sports Illustrated.

While the high point of Turner’s sailing career was his win over Alan Bond’s Australia in the America’s Cup Race, he had success before and after, including wins in the Flying Dutchman World Championships, Congressional Cup, 5.5 Metre Gold Cup, SORC, the Miami-Montego Bay Race and the storm-ravaged 1979 Fastnet Race in which he skippered the 61-foot Tenacious (a 1971 S&S design) to victory.

Turner founded Cable News Network (CNN) in 1980, which revolutionized news reporting by providing access to worldwide news 24/7. Turner was also a four time Rolex Yachtsman of the Year and in 2017 was awarded the New York Yacht Club Medal, the highest individual honor the Club can bestow. He also won a World Series as the owner of the Atlanta Braves, created the Goodwill Games, is a member of the Television Hall of Fame and a former Time magazine Man of the Year (1991). A documentary entitled Courageous was released in 2017. For a preview of the documentary, click here. My favorite quote of Ted Turner's is "The chance for mistakes is about equal to the number of crew squared."


Larry Ellison

Larry Ellison, founder of Oracle, purchased the maxi-yacht Sayonara specifically to race her  in the ill-fated Sydney to Hobart race in 1998. She was just about the largest yacht allowable, and money was no object -- he just wanted to win. He skippered her to line honours and considered that a life-changing event. Today, Ellison spends much of his free time sailing and vacationing on one of two motor yachts that he keeps in separate oceans.


Albert Einstein

Einstein may have been a genius when it came to physics, but by all accounts he was not much of a sailor. He learned to sail in Switzerland and continued to sail after emigrating to the United States. He lived in Saybrook and sailed on the Connecticut River, making local headlines on several occasions. We've sailed the River and it can be tricky, with silting at the mouth and shifting shallows. But it seems it was more a matter of preoccupation that got Einstein, who didn't swim, into difficulty.



Kenneth Graham

Jack London

Joseph Conrad

There's a famous person who sailed in my background. Joseph Conrad, nee Józef Teodor Konrad Korzeniowski, was a sea captain who became perhaps one of the world's greatest novelists. He spent almost 20 years at sea before publishing his first novel. About half of his books are about the sea and most of his protagonists are modelled on real people he met along the way. I am always so honoured to think that I am a distant relative (nee Daria Olena Korzeniowski). I have not been able to ascertain whether he continued to sail for pleasure after giving up the merchant marine. Given his ill health, I am inclined to believe he did not.

Here's a post about a few sailors who had an enormous impact on sailing and another post about famous female sailors who ventured offshore (not around the marks).

If I missed anyone, please leave a comment with their names. I'll try to add more details about those listed here as time permits.


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