Admired for their elegance and desired wherever they go, classic yachts attract a large number of owners and charterers. For those wanting a genuine sailing experience or who want to capture the real romance and thrill of yachting, these historic beauties have an enduring appeal. Every classic has a unique story to tell — whether it’s racing with royalty or hosting the Hollywood elite, or perhaps even serving in the war effort.
And each of the yachts featured here defined the glamor of her respective era. But what is it about these storied vessels that makes every generation of owners prepared to sink time and financial resources into their restoration? Here are 10 of the most exquisite classic yachts afloat today, a handful of which are available for the yacht aficionado to charter or even own.
Builder: Ramage & Ferguson
Refit: 1955, 1991, 2002, 2006, 2007, 2020
LOA: 150.1 ft
Number of guests: 10
One of the finest vintage yachts afloat, Kalizma (pictured top) has an iconic past with a tale steeped in history. Originally commissioned by Robert Stewart, vice commodore of the Royal Eastern Yacht Club (whose wealth came from his Scotch whisky distillery and estate), Minona, as she was named upon her launch, was the first steam-powered yacht to have electric lighting.
Designed by naval architect GL Watson & Co, leading designers of their day, and built by Ramage & Ferguson in Scotland, she is a testament to expert craftsmanship — and has stood the test of time with her classic Edwardian looks and fresh contemporary updates.
As Minona, she served in the British Royal Navy in both World War I and World War II, serving as an Auxiliary Patrol Vessel between 1914 and 1920, and in 1939 as HMS Minona. During her time as the flagship and base for His Majesty’s Deep Sea Rescue Tug Services in Scotland, she was responsible for saving the lives of crewmen from over 1,100 vessels.
On being relieved from her wartime duty, Minona went on to have a couple of different owners during the 1940s and ’50s, and during that period she also underwent a significant refit converting her from steam to diesel. It was during the 1960s that the then-named Odysseia made headlines when chartered by Richard Burton and his wife Elizabeth Taylor, and thus began her dalliance with glitz and glamour.
As a frequent guest of Aristotle Onassis aboard his yacht Christina O, Burton was inspired to purchase the classic yacht as a congratulatory gift for Taylor after she earned an Academy Award for her performance in Who’s Afraid of Virginia Woolf? The yacht was subsequently renamed Kalizma, after the stars’ children Kate, Liza and Maria, and refurbished with all new interiors said to have cost more than twice her asking price. Adorned with an art collection with works by Monet, Van Gogh and Picasso, and an extensive library, she became their floating home for the next decade.
It was on board Kalizma while berthed on the River Thames that Burton presented Taylor with the 33-carat Krupp Diamond, also known as the Elizabeth Taylor Diamond. Then, while berthed in Monaco, he gave her the record-breaking $1.5m 69-carat Cartier diamond, which arrived under police escort. Taylor wore the jewel, which became known as the Taylor-Burton Diamond, for the first time on a necklace at Princess Grace’s 40th birthday party.
A number of royalty, including Princess Grace of Monaco and Prince Rainier III, and distinguished personalities such as Rex Harrison and Tennessee Williams, were later guests of the most famous Hollywood couple during their high-profile ownership.
Kalizma has gone on to have a number of owners since then, including serial classic yacht owner Peter de Savary. Kalizma was de Savary’s flagship and floating headquarters for the British team at the 1983 America’s Cup challenge, hosting several spectators in Newport.
Acquired by Indian tycoon Vijay Mallya in 2006, and then by philanthropist Shirish Saraf in 2019, she has since been fully restored, rejuvenating her old-world charm with all the luxuries and amenities expected of a modern superyacht. Today she is available to charter in the Indian Ocean and Asia Pacific with accommodation for 10 guests in five staterooms, including a stunning master suite, two doubles and two twins.
From €90,000 to €100,000 (approx. $101,800 to $113,100) per week. Contact Tim Morley, founder, firstname.lastname@example.org, +33 680 863 091, morley-yachts.com
Shenandoah of Sark
Builder: Townsend & Downey
Refit: 1972, 1996, 2018
LOA: 178 ft
Number of guests: 10
Built at the turn of a century for American banker Charles Fahnestock, Shenandoah, as she was then known, was one of the most high-profile yachts of her age and a symbol of one the most glamorous eras in yachting. Delivered in 1902 by the Townsend & Downey Shipyard in New York, she quickly gained a reputation not only for her celebrated design but for the parties held on board.
During these formative years Shenandoah played host to some of the world’s most powerful families and international royalty while in her homeport of Newport, Rhode Island. A few years later, Fahnestock retired and sailed her to the Mediterranean, where her reputation as one of the most elegant sailing yachts on the circuit was solidified, with parties held along the Côte d’Azur and Amalfi Coast becoming the most sought-after ticket for the yachting fraternity.
While cruising the Mediterranean, Shenandoah turned the head of German aristocrat Landrat Walter von Bruining, who went on to purchase the three-masted schooner and rechristened her Lasca II. Under Bruining’s ownership, Lasca II spent time in Germany and England, where he enjoyed just one summer in Cowes on the Isle of Wight before World War I broke out.
Commandeered by the British, she subsequently became the property of British shipbuilder Sir John Esplen, who reinstated her previous name and installed two engines on board. Shenandoah then went through a number of different names and owners, including an Italian prince and the Danish sculpture philanthropist, Viggo Jarl, between the wars. Jarl endowed a substantial part of his fortune on the renamed Atlantide, updating her with new diesel engines and an electricity plant, and embarking on a series of long passages to the West Indies and through the Panama Canal to South America.
At the onset of World War II, Jarl returned to Europe and hid Atlantide from the Nazis, removing her masts and engines to render her useless to either side. Surviving the war, and with her engines and masts reinstated on board, Atlantide continued to turn heads wherever she cruised, and also welcomed European royalty on board, including the Duke and Duchess of Windsor.
After surviving two World Wars, Atlantide’s run of good fortune was apparently over. During the next few decades she went ‘underground’ and is rumored to have seen her fair share of smugglers and gamblers, cruising throughout the Americas and Caribbean, before ending up in the Mediterranean, where she was seized by the French government in a tax scandal.
Following many years of neglect, she was rescued in 1972 by the inventor of the Bic ballpoint pen, Baron Marcel Bich. Restored to her former splendor and christened Shenandoah once again, Bich sailed the yacht back to America as a spectator boat for the America’s Cup — the first time she had been back to her original homeport of Newport for over 70 years.
Shenandoah spent several years under Bich’s ownership, immaculately maintained, before being purchased by industrialist Philip Bommer. Having witnessed Shenandoah sailing when he was just 13, Bommer had spent the ensuing two decades dreaming about owning her, and in 1986 his ambition was fulfilled. Extensively refit and restored once again, Shenandoah became a renowned charter yacht, before once again entering years of neglect.
Rescued once again, refit and refurbished, Shenandoah was an America’s Cup spectator for the second time, this time in New Zealand in 2000, before competing in the Millennium Cup superyacht regatta. Five circumnavigations later, with a number of successful transatlantic races and classic regattas under her belt, and via a number of owners and award-winning refits, the rechristened Shenandoah of Sark is today a perfectly preserved piece of sailing history.
Builder: Canadian Vickers
Refit: 1954, 2001, 2015, 2018
LOA: 325.3 ft
Number of guests: 34
Christina O is a part of yachting legend. Arguably the most famous classic yacht still afloat, the fabled yacht of Aristotle Socrates Onassis has regularly entertained some of the world’s most powerful and famous people. She may not be a classic beauty like Delphine and Talitha but, thanks to the lavish parties hosted aboard by Onassis, with guest lists full of some of the most well-known names of the time, including Frank Sinatra, Marilyn Monroe, Richard Burton and Elizabeth Taylor, Christina (as she was then known) regularly featured in newspapers and on the cover of glossy magazines.
Becoming a part of the zeitgeist of her era — and as famous as some of the Hollywood stars who came aboard — she remains today a visible symbol of the glamorous lifestyle enjoyed by the yachting crowd from the late 1950s throughout the ’60s.
Originally built in 1943 as a Canadian naval frigate, Christina O remains the largest North American-built yacht still afloat. Purchased by well-known yacht owner and Greek shipping magnate Onassis in 1954, she was converted into the yacht that she is today. It is rumored that Onassis purchased the then-named HMCS Stormont for its scrap value of $34,000, and then spent over $4m converting the surplus anti-submarine frigate into the luxury yacht Christina, named after his firstborn child.
In those days this was a vast sum of money, but the investment paid off. Not only did Christina hugely enhance his status and fortune — as a venue for hosting businessmen and politicians, as well as film stars — but she also served as the backdrop for his famous romantic relationships, including his love affair with the renowned soprano Maria Callas. It was on board the converted frigate that John F. Kennedy met his idol Winston Churchill during a dinner hosted by Onassis, and a decade later where Onassis began his courtship of the widowed Jackie Kennedy. The yacht was even their wedding venue.
Despite seeing some deterioration under the ownership of the Greek government, Christina O has been refurbished and refitted; today she retains the fantastic opulence Onassis so extravagantly bestowed on her. In fact, she positively oozes ’50s Hollywood glamor; it could even be said she has only improved with age. As an in-demand charter yacht, her eternal appeal to a modern clientele is proven.
All the modern comforts and luxuries that are expected on a luxury yacht seamlessly blend with her original features. All of the 17 guest suites have been refurbished, yet maintain the pastel decor selected by style icon Jackie O. The original, mosaic-tiled pool that transforms into a dance floor has also been restored, while the famous Ari’s barstools retain their original upholstery, believed to be sperm-whale foreskin — now there’s a conversation starter when you are perched at the bar.
Christina O is currently cruising the Caribbean and will be available for charter throughout the summer in the Mediterranean. The perfect yacht for large family groups or event charters, her SOLAS status allows up to 34 guests to cruise in total comfort in 17 double staterooms, 14 of which can be converted into twin staterooms.
Builder: Camper & Nicholsons
Refit: 1947, 2009, 2013, 2018
LOA: 147 ft
Number of guests: 16
With a unique and historic pedigree, the Camper & Nicholsons-built Grace has led many lives during almost a century afloat. Built as a luxury yacht in 1928 and originally christened Monica, she was used by the British as part of the war effort. While serving in the Royal Navy as HMS Rion, she sadly suffered serious damage as part of the Dunkirk evacuation fleet.
Rescued by Aristotle Onassis in 1951 and renamed Arion, she played host to iconic figures like Winston Churchill and Elizabeth Taylor. On hearing of Prince Rainier’s engagement to Grace Kelly in 1955, Onassis presented the classic motor yacht to them as a gift for their forthcoming 1956 nuptials.
She was renamed Deo Juvante II, and the couple honeymooned aboard her, cruising Corsica and Sardinia. Acquired by the current owners in 2007, she spent more than two years in the shipyard being restored to her former glory and having additional superyacht luxuries installed, including air conditioning and en-suite bathrooms.
Rechristened Grace, she is available for charter in the Galápagos Islands for up to 16 guests and 12 crew. Great attention to detail has been given to restoring her original features, including the original brass ship’s wheel from 1927, which is still inscribed with the yacht’s original name. The master suite, known as the Grace Kelly Suite, is in the original location, while two further master suites and two twin-bedded cabins are all decorated to the highest standards.
Her communal guest areas feature period-style, custom furniture in keeping with her elegant build. In addition to her alfresco dining and lounging areas and hot tub, the toybox is geared towards exploring the Galápagos National Park and includes kayaks, snorkeling equipment and two Zodiac tenders.
Builder: Great Lakes Engineering Works
Refit yard: Scheepswerf Zeebrugge
Refit: 1926, 1997, 2003, 2016
LOA: 258 ft
Number of guests: 26, 150 day guests
Commissioned by auto magnate Horace Dodge and named after his only daughter, Delphine is the largest steam-powered yacht ever to be built in the US. Sadly, Horace never got to see the launch of this third private yacht he built, as he passed away just a year before her delivery. However, his wife Anna and their family loved and cherished Delphine, cruising on board her in the Great Lakes and along the East Coast, hosting cocktail parties on board.
With all her luxuries, including 10 magnificent staterooms, a music room, card room, dining room and smoking room, and a crew of 55, she positively defined 1920s East Coast glamor. In 1926, while she was docked on the Hudson River in Manhattan, two cabins caught fire, and with too much water poured in by the fire department, Delphine sank. Unwilling to live without her, the Dodge family salvaged her from the deep and restored her faithfully, with some additional renovations to her interior.
She suffered further, minor damage when she ran aground in the Great Lakes, before being repaired and acquired by the United States Navy at the start of the war to become the flagship for Admiral Ernest King, commander-in-chief of the US Fleet and chief of US Naval Operations during World War II. While still in service as USS Dauntless, she reputedly hosted Franklin Roosevelt, Winston Churchill and Viatcheslav Molotov as they met with Admiral King to discuss war strategies and prepare the Yalta Convention.
Reacquired by the Dodge family after the war, she was restored to a private yacht and rechristened Delphine once again. Over the next three decades Delphine sailed under numerous ownerships and different names, including almost 20 years spent as a training ship for merchant seamen, until finally being sold (for scrap metal prices) in 1997.
Having crossed the Atlantic for the first time and berthed in the Mediterranean, she was towed to Bruges, Belgium, where she underwent a six-year, $60m restoration. Her new Belgian owner scoured museums and archives for Delphine’s original blueprints, in an effort to ensure that the engineering and architectural refit was faithful to her original design, right down to the 20-ft-tall quadruple steam engines, six-person Turkish bath and hairdressing salon. Even her bespoke tenders, handmade from Honduran mahogany, remain exactly as they were when she was brand new.
Rechristened in 2003 as Delphine by HSH Princess Stéphanie of Monaco, she is today the largest luxury yacht of her era with her original steam engines still in service. To put that into context, her 6-ft-tall propellers are powered by water converted into vapor pressure by diesel fuel. She consumes 600 liters an hour at cruising speeds. When you consider that many modern motor yachts of a similar size use more than 1,000 liters of fuel an hour, Delphine could almost be considered environmentally friendly. Full steam ahead.
Builder: Friedrich Krupp Germaniawerft
Refit yard: Pendennis
LOA: 233 ft
Number of guests: 12
At the time of her launch in 1929, this clipper-bow yacht was christened Haida, after the native people of Alaska and British Columbia. It is the name for which she is best known, and to which she has recently reverted following a comprehensive refit. However, the iconic Haida has sailed through a succession of adventures and has had many different names during her storied life.
Haida’s original commissioning owner spent over a decade cruising the west coast of America, pursuing his interests in marine science and fishing. In 1940, the oceangoing yacht was commandeered for service in World War II by the US Navy. She had a heroic naval career, saving many lives and protecting key installations while patrolling San Francisco Bay.
In 1946, post war, she returned to her role as a private yacht and moved to Alexandria in Egypt, where she cruised for five years before moving to the French Riviera in 1952 — just in time for the birth of the Mediterranean yachting scene.
She has resided in the Mediterranean ever since, under various ownerships of dedicated, high-profile owners, including Löel Guinness, becoming one of the world’s most famous superyachts.
Haida’s recent, award-winning refit by the renowned Pendennis Shipyard has combined the grandeur and elegance of 1930s yachting with state-of-the-art superyacht luxuries. Despite replacing over 100 tons of steel within her hull structure, Haida 1929 (as she is now known) retains the sophisticated and timeless exterior lines originally designed by Cox & Stevens.
Even the original Krupp engines remain, thought to be the oldest working engines of their type. Deck spaces are generous, especially on the recently extended sun deck, which has been split around her iconic funnel. Period furniture and artworks re-create the charm and ambience of her heritage, while a light color palette and modern amenities have been integrated.
Her notable features include a barber shop, spa, hammam, biofuel fireplace, indoor and outdoor cinemas, and stepped pool. Elegant and refined, Haida 1929 is a truly original classic. Refit project management by Edmiston Yachts.
Builder: Georgi Dimitrov
Number of guests: 12
She may not hail from the golden era of yachting like other classic yachts her size, but this former Soviet spy ship is certainly not short on history. A true gentleman’s yacht, La Sultana has led many lives during her 50-plus years afloat. Originally built in 1962 in Bulgaria for use as a passenger ferry, Aji-Petri (as she was then known) was the fifth of a series of 12 ships that carried passengers and cargo through the Black Sea between the ports of Istanbul and Yalta.
She became a Soviet spy ship in the early 1970s when the Soviet Union took over the entire fleet of passenger ferries operating in the Black Sea to use for military purposes. Officially, she was in service in the North Atlantic for the International Telecommunication Union; however, in reality she was being used to eavesdrop and intercept radio telecommunications between the US and the UK. After the dissolution of the Soviet Union, Aji-Petri resumed her position as a passenger ferry before being used, in her original form, as a pleasure yacht in Tunisia.
Some 50 years after her build, she was discovered by a French gentleman. It was during a colossal seven-year, multimillion-dollar restoration in Casablanca that the yard unearthed several espionage instruments, including a radioactivity detector and several electronic devices from the Cold War. With the addition of her raised bow, touch-and-go helipad, machinery, piping and wiring, commercial engine and a huge keel, the rechristened La Sultana emerged from the shipyard as a majestic cruising yacht.
Today, her striking interior features Art Deco touches that draw inspiration from the stylish vessels of the 1920s, while the Arabian Nights-inspired decor is both eccentric and exotic. The new layout features an indoor 16-ft counter-current swimming pool and hammam, and seven luxurious staterooms, including a vast master suite on the upper deck, two VIP staterooms on the main deck, and four staterooms on the lower deck, all with en suites — quite a difference from the original build with its 102 cabins.
Her large deck areas include lots of relaxation and entertainment areas, as well as a classically styled spa pool on the foredeck, located forward of the new helipad. With more than a nod to the golden age of yachting, the rebuilt La Sultana is a classic motor yacht for modern times.
Builder: Camper & Nicholsons
LOA: 164 ft
Number of guests: 10
Designed by Charles E Nicholson and built by Camper & Nicholsons in 1937, Malahne is one of just a handful of British-built, pre-war motor yachts to have survived into the 21st century. Originally commissioned by William Stephenson, head of the British arm of the Woolworth store chain and a passionate yachtsman, this classic 1930s gentleman’s yacht has led a glamorous and colorful life, with many ups and downs. Stephenson owned both the J-Class yacht Velsheda and Malahne, and named them after his daughters Velma, Sheila and Daphne, with the first few letters of their names forming ‘Velsheda’ and the last few letters ‘Malahne.’
She spent her first few years cruising the Mediterranean, and crossed the Atlantic a number of times before being handed over for military needs during World War II. During her time serving as a patrol cruiser in the English Channel, Malahne also participated in the evacuation of troops from Dunkirk.
Post war, Malahne passed through a few different hands before being acquired by the legendary Hollywood producer Sam Spiegel, who anchored her off Jordan to be used as a floating office while shooting Lawrence of Arabia. On retiring from her filming duties, Malahne became a fixture along the glittering Côte d’Azur, where Spiegel entertained Hollywood A-listers including Frank Sinatra, Elizabeth Taylor, Grace Kelly and Jack Nicholson. She also starred in the 1973 murder mystery The Last of Sheila, starring Raquel Welch.
A decade later, she was sold to a Saudi sheikh who renamed her Adel XII and changed her beyond recognition, with an almost sacrilegious angular new superstructure and modern interior quite out of keeping with her classic past. Twenty years later, she passed into more sympathetic hands, and underwent a hugely ambitious restoration at the British shipyard Pendennis. The restoration experts there sought to bring her back to her original classic yacht form, but with the addition of a few 21st-century comforts.
While Pendennis worked on recreating her original hull form and undoing the damage wrought by the previous owner, classic yacht experts GL Watson & Co were drafted to rework her exterior lines; meanwhile, design experts from Oliver Laws — who designed the Art Deco interiors of the Connaught hotel and Claridge’s — set to work on her interior, producing a design more faithful to the original, including a number of original antique 1930s pieces but with a modern Art Deco twist.
Today, thanks to such a comprehensive and sympathetic refit by her devoted British owner, Malahne is a tribute to modern engineering and British craftsmanship. One of the finest classic yachts for charter, she features state-of-the-art equipment and Art Deco interior styling. Were he still alive, there’s no doubt that Sinatra would be delighted to tap his dancing shoes once again on board her stunningly restored teak decks.
Builder: Friedrich Krupp Germaniawerft
Refit: Devonport Yachts
Refit: 1993, 2009
LOA: 262 ft
Number of guests: 12
With her flared clipper bow, impressive funnels and traditional counter stern, there couldn’t be a more classic-looking yacht reflecting the golden age of yachting than Talitha. Originally commissioned by Russell Algar of the Packard Motor Car Company, the originally named Reveler was sadly not yet delivered by the German shipyard F. Krupp in Kiel when Algar died.
Sold to Charles McCann of the Woolworth family and renamed Chalena, she was later requisitioned by the US Maritime Commission in 1942, and entered service as a gunboat with new armaments mounted fore and aft. Operating under her new military name of USS Beaumont in the waters between Midway Island and Pearl Harbor, she survived the war without serious incident, and in 1946 was decommissioned and returned to private ownership.
Post war, like many of her classic cousins, she spent many years lying abandoned — in her case on the Greek island of Petali, before being rescued by the Australian film producer Robert Stigwood and renamed Jezebel. Stigwood spent millions restoring much of her original elegance, with the addition of modern comforts including air conditioning and satellite communications systems.
Described by The New York Times as a “floating fantasy,” she featured a re-design of the distinctive clipper bow and new teak decks but, sadly, it wasn’t to last and, following some engine problems, she was laid up once again in the late 1980s. In 1993 she was brought to the attention of her next and current owner Sir John Paul Getty Jr.
Under the guidance of legendary designer Jon Bannenberg, she was painstakingly restored to her former glory, with both exterior and interior redesign and brand new engines. The addition of a pair of funnels and an extended wheelhouse was at the time criticized by many, but Bannenberg’s vision proved them wrong when the renamed Talitha G (named after Getty’s second wife) was relaunched to great acclaim, with more than a nod to her 1930s design.
One of the most detailed, distinctive and beautiful classic motor yachts to be relaunched in recent times, Talitha is suitably reflective of an incredibly glamorous era of yachting. Featuring an all-new Art Deco interior with all of the trappings of a modern classic, she is a real head-turner, not only for the Hollywood celebrities spotted on board, but for her own stunning looks.
Builder: Brooke Marine
Refit: 1999, 2016, 2019
LOA: 115 ft
Number of guests: 8
Delivered in 1939 by British shipyard Brooks Motor Craft, the classic sailing yacht Eros has led a colorful past, with lords, ladies and royalty all captivated by her charm and beautiful lines over her eight decades afloat. Originally christened Jeanry, she was commissioned for the daughter and son-in-law of a British lord who unfortunately spent very little time on board her before she was requisitioned by the Royal Navy to participate in the evacuation efforts at Dunkirk during World War II.
Following the end of her wartime service she went on to be owned by Greek shipping magnate Stavros Niarchos, second only to Aristotle Onassis in the shipping magnate stakes and also the first man to be called a billionaire. Niarchos rechristened her Eros in honor of the Greek god of love and passion, and under his ownership the wooden schooner became a fixture on the Mediterranean yachting circuit, hosting the cream of European society, including King Juan Carlos and Queen Sofia of Spain.
Niarchos gifted the newlyweds the use of Eros along with his private Greek island, Spetsopoula, for their honeymoon in 1962. The island also hosted Prince Charles and Princess Diana for the latter part of their honeymoon while they cruised through the Mediterranean and Aegean on board the Royal Yacht Britannia.
Eros went on to change ownership just one more time before being rescued by her current owner in 1992. Meticulously restored to her original grandeur over the course of 18 years, she was relaunched in 2016 and now offers the refinement of a bygone era combined with the latest superyacht luxuries. Retaining many original details, including the Admiralty bronze fittings of the ship’s bell and restored Burmese teak planks, her complete overhaul involved repairs and replacements to her steel structure, and over 20,000 new bronze bolts, among many other things.
Today, Eros offers charter guests the chance to experience genuine sailing on a stunning classic yacht, either cruising in the Caribbean or Mediterranean or racing in classic regattas in the Caribbean and New England. Boasting state-of-the-art technology, 22 hydraulically assisted winches and 9,000 sq ft of sail, Eros can reach speeds of up to 10 knots under sail.
And for those looking to simply sit back and relax, her four guest cabins include a master stateroom with private en suite featuring a Jacuzzi bath, a double stateroom with en suite, and two twin cabins with shared bathroom. Out on deck, she boasts numerous seating and lounging areas for socializing, relaxing and alfresco dining.
Eros also offers plenty of on-the-water entertainment, with a great selection of water toys for her more active guests to enjoy.