Beyond striking a cutting figure, classic yachts offer more than the routine experience of most modern charter yachts. These vessels are living narratives—laden with stories and personalities from bygone eras—with details that carry a legacy of old-world sophistication and finesse: Think Christina O’s distinctive swimming pool or Shenandoah of Sark’s dramatic sail plan.
“Whenever I step on board a classic yacht, I like to imagine where the yacht has cruised through the decades,” says charter broker Céline Pujol. “Who were the guests who stepped onboard?” Christina O, for example, served as a wedding venue for people ranging from supermodel Heidi Klum to Prince Rainier III of Monaco, who wed Grace Kelly in 1956. This vessel also hosted an unusually large share of prime ministers, presidents and celebrities, so that a charter today could mean sleeping or eating in the same areas as Winston Churchill, JFK, Frank Sinatra, or Elizabeth Taylor.
Time is the essence of a classic yacht, Céline explains. “First, you travel back in time, being onboard a unique piece of history. Second, the travel actually takes time, because these yachts aren’t fast. But that allows you to indulge and live each moment to the fullest. You simply can’t rush from one place to another.”
With many vintage vessels, both power and sail, now part of the global charter fleet, a growing number of charter clients are considering immersing themselves in the rich, wood interiors, eating at formal dining tables with 1930s china, or gazing out at the ocean from deck-chairs. The experience, really, is not comparable to life aboard a modern yacht. Many charter guests are asking themselves: Why chase trends when you can relive history?
Here are nine of our favorite classics.
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‘Marala’
Image Credit: Claudio Arpino/Ocean Independence Built in 1931 by Camper & Nicholsons, Marala is one of the few surviving yachts of that time, and as a result, carries a remarkable history. It served as a navy vessel during World War II and later played host to distinguished guests that range from Salvador Dalí to Frank Sinatra. The 193-footer recently completed an extensive two-year refit by Pendennis. The yard worked with Muza Labs to restore the original 1930s Art Deco design, including the beautiful copper Jacuzzi on the aft deck. The vessel comfortably accommodates 12 guests across six cabins. Marala is available for charter with Ocean Independence.
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‘Shenandoah of Sark’
Image Credit: Northrop & Johnson Commissioned by a wealthy New York banker, this steel-hulled, 178-foot three-mast schooner launched in 1902 and went on to have one of the most interesting histories of any 20th century yacht. It was owned by German industrialists, British aristocrats, and even an Italian prince. The four-stateroom vessel underwent a total refurbishment in 1995 and has had four refits since, bringing it back to its former glory with plenty of modern features. The classic interior is filled with wood and brass fittings, sculpted glass, and even a grand piano—though it also has a state-of-the-art entertainment system as well as Wi-Fi and multiple water toys. If you want to experience what the Golden Age of Yachting was like, Shenandoah of Sark, available through Northrop & Johnson, is your vessel.
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‘Christina O’
Image Credit: Morley Yachts Perhaps the best-known classic yacht on the charter market, 325-foot Christina O’s timeless lines have served as inspiration for many modern builds. Originally built in 1943, the vessel started life as an anti-submarine frigate in Canada’s navy, serving in World War II in the D-Day landings and Battle of the Atlantic. In 1954, it was purchased by Aristotle Onassis for scrap before undergoing a $4 million refit. The boat went on to play host to Prince Charles and Princess Diana, Marilyn Monroe, Elizabeth Taylor, Frank Sinatra, Winston Churchill, and Jackie and John F. Kennedy, as well as for the wedding of Prince Rainier III and Grace Kelly. Today, Christina O is a celebrity in its own right, having been featured in The Crown and Triangle of Sadness. The boat is best known for the canoe stern and bronze-edged mosaic swimming pool that transforms into a covered dancefloor. With accommodations for up to 11 guests in six cabins, Christina O is available for charter through Morley Yachts.
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‘Monara’
Image Credit: Camper & Nicholsons Monara is a classic gentleman’s yacht, once the pride of a wealthy Milanese banking family and later purchased by an English aristocrat. The 84-foot vessel has also played host to Spanish royalty. It’s now a proud member of the Feadship Heritage Fleet. The Dutch yard rebuilt the vessel in 2016. As a charter vessel, it combines a timeless aesthetic with state-of-the-art amenities and plenty of deck space. Monara can accommodate eight guests across four cabins. It is available for charter through Camper & Nicholsons.
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‘Over the Rainbow’
Image Credit: TWW Yachts Over The Rainbow has enjoyed a colorful past. After being launched in 1930 and cruising the U.K., the 114-footer was commandeered by the Royal Navy at the start of World War II. Called HMS Corax, the vessel was used as a coastal patrol boat. The navy officers enjoyed their time onboard—the evidence of their favorite pastime, darts, can still be seen on its original Honduras mahogany panels. Post-war, Over the Rainbow was taken across the Atlantic to cruise the U.S. until making its way back to the Mediterranean for use as a floating casino until 2000. Then it was painstakingly restored and put to charter. It has enjoyed visits from celebrities ranging from Churchill to Madonna, who made a video while staying on board. Over The Rainbow houses a collection of literature by authors like Ernest Hemingway and has the alfresco deck space for reading, eating and entertaining. It accommodates 11 guests across four cabins. The vessel is available for charter through TWW Yachts.
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‘Malahne’
Image Credit: George Glaisher/Edmiston Meticulously restored to its original opulence, Malahne is an Art Deco masterpiece built by Camper & Nicholsons. The 177-footer was delivered in 1937, spending the first few years sailing around the world before serving in World War II, specifically at the evacuation of Dunkirk. It later went on to become one of the most famous yachts of Hollywood’s elite after being purchased by Oscar-winning film producer Sam Spiegel (Lawrence of Arabia and The Bridge on the River Kwai), who hosted Elizabeth Taylor, Frank Sinatra, Jack Nicholson, Grace Kelly and Kirk Douglas. The interior experienced a recent makeover by Scottish designer Guy Oliver, also responsible for the styling of 10 Downing Street. Rich in historic details, the vessel features a comfortable full-beam master suite, and four other suites for groups up to 10. Malahne is available for charter through Edmiston.
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‘Astarte’
Image Credit: Natua The story of Astarte, a classic wooden schooner, matches the life of Greek shipping magnate, John S. Latsis. Ranked as one of the richest men of all time by Forbes magazine, Latsis commissioned the Psarros Shipyard to build a classic yacht from wood. Alcyone, as the vessel was first named, hit the water in 1964, where it eventually hosted Prince Charles and Princess Diana, Marlon Brando, George Bush, and the Saudi royal family. Today, the 79-footer’s classic lines hark to a bygone era of elegance and luxury. Those themes are evident in the salon decorated with giant nautilus shells, gorgons of the sea and other old nautical items. The tea and coffee services are authentic 1930s art deco, as is the Brazilian rosewood bar. The boat even has a wine cellar. Based in Greece, Astarte can comfortably accommodate nine guests across four cabins. The boat is available for charter through Tahiti Yacht Base.
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‘Sherakhan’
Image Credit: Y.CO When the owner of the 228-foot Sherakhan was thinking of a name for the yacht, his daughter was watching The Jungle Book. Inspired by the book’s Bengal tiger, the name matched the incredible vessel, which sleeps up to 26 guests in 13 cabins. With its ice-class hull, Sherakhan has explored the most remote corners of the globe, including the Arctic and Antarctica, the Galapagos, and the South Pacific. A collection of curios—including a number of first-edition literary works—add an old-world charm. The vessel’s open 26-seat dining atrium also not only provides ample space for events, but is ideal for multi-generational cruising. Sherakhan is listed for charter through Y.Co.
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‘Kalizma’
Image Credit: Tim Morley Delivered in 1906, Kalizma—originally named steamboat Minona—was one of the first vessels with electric lighting. The 150-footer went on to serve in both world wars, and its steam engines were eventually converted to diesel. By the 1970s, it was one of the most famous yachts in the world, largely thanks to Richard Burton’s purchase as a gift for Elizabeth Taylor. It was eventually bought by a new owner. Brad Pitt once reportedly enjoyed his time on board so much, he tried to buy the vessel. Today, Kalizma’s beautifully updated interiors, ample deck space and enviable history make it a popular choice for charter. The boat can accommodate up to 10 guests across five cabins. It is available for charter through Morley Yachts.
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