Princess Diana and the New Year she never loved inside Sandringham's stiff traditions

Princess Diana never did pretend that royal tradition suited her and nowhere was that more obvious than at Sandringham on New Year’s Eve.

While the late Princess of Wales is often remembered for her warmth and glamour, insiders say she found the monarchy’s holiday rituals deeply uncomfortable. 

Christmas at Sandringham was famously not her scene, and ringing in the New Year there proved little easier. 

For Diana, the festive season with the Royal Family felt less like celebration and more like endurance.

Traditionally, the Windsors spent New Year’s Eve holed up at the Norfolk estate, sometimes remaining there well into February. 

Queen Elizabeth II, a devoted traditionalist, marked the occasion with a structured routine that included a church service at St Mary Magdalene, a formal dinner, and weather permitting a pheasant shoot. Festivities were polite, restrained and steeped in protocol.

One of the late Queen’s favourite New Year customs was something known as a “lucky dip.” 

According to royal biographers, a butler would bring out a container filled with sawdust and folded notes predicting fortunes for the year ahead. 

Family members would take turns drawing one and reading it aloud — a gentle ritual that delighted Elizabeth but reportedly left Diana feeling ill at ease.

As midnight approached, the Queen would quietly retire for the night, triggering an unspoken rule that no one else should head to bed before her. Only once Elizabeth had withdrawn would the evening officially end.

For the Princess, those long hours of polite small talk were reportedly unbearable. 

Former palace aides later recalled how she struggled with the expectation to sit through extended evenings of conversation, waiting for permission implicit or otherwise to escape. 

On more than one occasion, she excused herself early, a move that raised eyebrows in royal circles and was seen as breaking with custom.

Friends of Diana have since suggested her discomfort wasn’t rudeness, but restlessness a reflection of how trapped she often felt within royal life.