Joshua Goldman
Joshua Goldman
min read · August 5, 2025 · Entertainment

Royal Yachting: From Windsurfing Winds to Secret Greek Retreats

A young Prince William and Kate Middleton on a yacht in Ibiza in 2006. This summer, the Prince and Princess have enjoyed a summer break in Greece

The Royal Roster: A Summer of Sun, Sea, and Scandal

The Mediterranean has long been a playground for royalty, and this summer was no exception. Thousands of families escaped to the sun-kissed shores, but none more so than Prince William and his family. The Prince and Princess of Wales, along with their three little rascals - George, Louis, and Charlotte - sailed into the Greek Islands on a £40million luxury yacht, leaving behind the pomp and circumstance of royal duties.

But this wasn't just any ordinary holiday. Insiders claim that 12-year-old George's eyes grew wide with excitement as he set foot on the tender boat, dispatched to Zakynthos for a special mission - allegedly, a fast food fix at McDonald's! The young prince, tired of traditional Greek fare like souvlaki and moussaka, craved the familiar taste of a Big Mac. But sources remain tight-lipped about the true purpose of the trip, fueling speculation that maybe, just maybe, Prince William was catering to his son's every whim.

Diana sunbathing on a diving board off the coast of Italy. This  would become one of the most iconic pictures of the late Princess

The royals' Greek escapades have brought back memories of Charles and Diana's carefree days on the high seas. The now-estranged couple, who would eventually divorce in 1996, enjoyed numerous yachting excursions across the Mediterranean during the 80s and 90s. In 1986, they were invited to Majorca by King Juan Carlos I of Spain, where they spent their days lounging on the beach and enjoying water sports.

But Charles's sailing days with Diana are a far cry from William's more private family trips. While the Prince has been keen to keep his family's holidays under wraps, his father was always game for a photo op. In one infamous image, Diana is seen diving off the side of the Spanish yacht into the sea, while Charles is windsurfing in the background.

Fast-forward to 2006, when William and Kate (then just courting) holidayed on the party island of Ibiza. They were invited to stay at Kate's uncle Gary Goldsmith's £3.6million villa, complete with an infinity swimming pool and tennis court. However, their hosts' love of wild parties soon earned the villa the nickname "La Maison de Bang Bang." The News Of The World infamously published a photo of Goldsmith snorting cocaine on its front page in 2009.

Pictured: the £40million yacht where the Waleses allegedly enjoyed a Greek getaway this summer

The royals have always been drawn to the Mediterranean's crystal-clear waters and picturesque islands. In 1991, Charles and Diana embarked on what would become their "second honeymoon" - a sailing trip along Italy's coast aboard the Alexander yacht. Joining them were the former King and Queen of Greece, as well as Prince Charles's cousin, Lord Romsey, and his family.

However, behind the scenes, rumors suggest that Charles and Diana's marriage was on shaky ground even then. The couple would eventually separate in 1992 and divorce two years later. Princess Diana continued to enjoy yachting holidays after her separation, often with her sons by her side.

One fateful summer in 1997 saw Diana sailing around southern Europe with Mohamed al Fayed and his son Dodi. The Princess met Dodi on this trip and the two quickly fell for each other. Tragically, their romance would be cut short just a month later when both Dodi and Diana died in a car crash in Paris.

Diana on holiday in 1991 on what was dubbed her and Charles' 'second honeymoon'

In recent years, Charles has continued to enjoy yachting with Camilla, his now-wife. In 2008, they embarked on a royal tour of the Caribbean by boat, visiting destinations like Jamaica and Trinidad and Tobago.

As for Prince William's family, their Greek getaway has been shrouded in secrecy - but sources close to the Palace hint that this may be their last private holiday before taking on more official duties. But one thing is certain: when it comes to yachting, royalty will always make waves.

Charles and Diana with a young Prince Harry and Prince William. The couple would separate just over a year after the holiday

Charles enjoying some windsurfing while on holiday in Majorca on King of Spain's yacht in 1986

Diana dives into the sea off the back of the King of Spain's yacht while on holiday in Majorca

Charles and Diana swimming in the sea off the coast of Sardinia. From what is known now their marriage was very much on the rocks by the summer of 1991

Diana aboard Mohammed al Fayed's yacht in Saint Tropez

Daily Mail coverage on August 5 1999 revealing that Camilla is set to join Charles on a yacht excursion to Greece

In 2008, Charles and Camilla embarked on a royal tour of the Caribbean where they travelled by boat to destinations such as Jamaica and Trinidad and Tobago