Princess Diana's cutest moments with Harry and William, from starting school to summer holidays

From the excitement of starting school to theme park fun, Princess Diana's cutest moments with Harry and William are numerous. The royal mother-of-two took a playful and supportive approach to parenting that seemed to bring out the best in her young sons.

Outside of palace doors, the princes' childhood was captured on camera. They were pictured with the Princess of Wales on a variety of occasions over the years, both before and after her split from their father Prince Charles. She was seen giggling with them at official engagements and getting up to mischief on holiday.

The result has been a heart-warming insight into the princess' special bond with her sons before she tragically passed away in 1997. Their tender moments - including plenty of silliness - are ones every parent can probably relate to. We've rounded up some of the most adorable, which you can't fail to smile at... 

Princess Diana's cutest moments with Harry and William

1. All smiles at the theme park

Princess Diana didn't seem to mind getting drenched with her sons on a water ride at Thorpe Park in 1993. The royal mother-of-two - who had separated from Prince Charles the year before - took their sons Prince William and Prince Harry on what appeared to be a very fun day out.

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2. Throwing a palace concert

One of the earliest joint photocalls between Prince William and Prince Harry was at Kensington Palace in 1985. Their mother, Princess Diana, looked every bit the doting parent as she helped the young brothers learn to play the piano.

3. First day of big school

Princess Diana couldn't hide her delight as she arrived with Prince William on his first day of secondary school - the iconic Eton near Windsor in Berkshire - in 1995. They were accompanied by Harry, who would go on to also become a pupil in 1998.

4. Loving the beach life

In 1990, Princess Diana took her sons on holiday to Necker Island, in the British Virgin Islands, which is owned by Sir Richard Branson. She was spotted getting stuck in as the princes dug up the sand along with some of their cousins - the children of her older sisters Jane and Sarah.

5. Mischief on the balcony

As is a rite of passage for royal children, Prince Harry could be seen playfully sticking his tongue from the balcony of Buckingham Palace while in the arms of an alarmed-looking Princess Diana. The pair - who were beside Prince William, Lady Gabriella Windsor and Lady Rose Windsor - were taking part in Trooping the Colour in 1988.

6. Holidaying in sunny Spain

Princess Diana, dressed in a chic yellow jumpsuit, was spotted cuddling up with her young sons in Palma de Mallorca, Spain 1987. The trio were holidaying, along with the future King Charles, on the invitation of the Spanish royal family - and Harry seemed to be faring in the hotter weather a little better than William. 

7. First day of little school

Every parent will relate to how Princess Diana seemed to be bursting with pride on Prince Harry's first day of primary school in 1989. Her youngest son posed for photos on the steps of Wetherby School in London, and looked adoringly up at his older brother who was already a pupil - with their matching uniforms adding to the cuteness. 

8. Travelling like a prince

The royal family may be more used to travelling by carriage than most, but Prince William and Prince Harry looked especially delighted to be using the novel mode of transport during a holiday to Lech, Austria in 1993. The trio, who were accompanied by the boys' nanny Olga Powell, grinned as they wrapped up warm in fur.

9. Action-packed garden playtime

Before her 1992 separation, Princess Diana raised her sons between an apartment at Kensington Palace in London and also on the country estate of Highgrove House in Gloucestershire. In 1986, she was pictured playing in the garden of the latter with William and Harry - who were dressed up in army costumes and taking turns on the slide.

10. Sledging through the snow

While it may not have had an official royal family holiday home, Princess Diana was a big fan of Lech, Austria for skiing. She could be seen laughing while sitting in between her young sons as they took a sledge ride through the snow during a trip in 1994, along with her friends Kate Menzies and Catherine Soames.

11. Taking in the sights

During an official visit to Canada in 1991, Princess Diana took her sons to see Niagara Falls in Ontario while the then-Prince Charles carried out engagements in Toronto. She was spotted, along with an inquisitive-looking William and Harry, wearing matching raincoats while riding on the 'Maid of the Mist' boat as they viewed the world-famous waterfall. 

12. Jetting up to Scotland

When visiting the late Queen Elizabeth at her Scottish home of Balmoral Castle, the royals would often travel by plane to Aberdeen Airport. On one occasion in 1986, Princess Diana could be seen holding her sons' hands and carefully guiding them across the tarmac. 

13. Wearing matchy-matchy outfits

Princess Diana was known to love dressing William and Harry in identical outfits as youngsters. During a trip to Scotland in 1986, the brothers could be seen wearing matching white sweaters and yellow shorts along with white socks and black shoes as they disembarked the plane with their mother. 

14. Looking smart for VJ Day

A year before her divorce was finalised, Princess Diana attended the official VJ Day 50th anniversary celebrations in London in 1995 with her sons. William and Harry walked close to their mother, whose white striped skirt suit - which she accessorised with a hat and pearls - was one of Princess Diana's best fashion moments.

15. Horsing around in the country

Prince William looked chuffed to be having a riding lesson from his mother Princess Diana on the grounds of Highgrove House, Gloucestershire in 1986. Her eldest child was pictured sitting atop their pony, called Smokey, while his younger brother seemed to be waiting his turn.

16. Making new furry friends

While the royal corgis may have been important to his grandmother, the late Queen Elizabeth, it seems a young Prince Harry wasn't quite so sure himself when it came to four-legged creatures. His mother Princess Diana could be seen encouraging him to get acquainted with a small dog while on holiday to the Spanish island of Majorca in 1987.

17. Learning the family business

Princess Diana was often seen helping her young sons feel at ease during some of their first royal outings as children. She was spotted giving Prince Harry a squeeze on his shoulders during a trip to Niagara Falls - his first official engagement abroad - on a visit to Canada in 1991. Meanwhile, Prince William appeared to be receiving words of encouragement.

18. Practicing the royal wave

At Trooping the Colour in 1989, a stylish Princess Diana beamed as Prince William and Prince Harry eagerly waved at crowds gathered near Buckingham Palace. The trio travelled in a horse-drawn carriage alongside the late Queen Mother, while their father rode on horseback as part of the annual royal event.

19. Thrills at the theme park

Princess Diana looked relaxed in a varsity jacket as she rode on a water ride with her sons and another youngster during a visit to the Alton Towers theme park in 1994. As is every parent's nightmare, she could be seen urging the giggling passengers to sit down as they all whizzed along.

20. Enjoying the sun in Spain

Clearly in a reflective mood, Prince William and Prince Harry were spotted calmly sitting beside their mother Princess Diana beneath the sunshine during a family holiday to the Spanish island of Majorca in 1988. They were staying at Marivent Palace, just outside of Palma, as guests of the then-King Juan Carlos and his wife Queen Sofia.

21. Fun on the slopes

Princess Diana was known for her love of skiing and clearly relished passing down the wintery hobby to her sons. She was seen riding a chairlift with Prince William and Prince Harry - both all adorably kitted out - during a holiday to her favourite resort of Lech, Austria in 1991.  

22. Twinning for the evening

Princess Diana sweetly loved putting her young sons in matching outfits where possible. At the Royal Tournament in London in 1988, she dressed them in particularly striking outfits - which included a shirt and tie, as well as bright green shorts.

23. Riding in Scotland

Every summer, Prince Charles and Princess Diana would stay up in Scotland with the late Queen Elizabeth at her country residence of Balmoral Castle. During one trip in 1988, Prince William was photographed gazing lovingly at his mother during a pony ride, as the family posed for photos.

24. Windy on the runway

While Princess Diana is famed for her sense of style, it's perhaps less well-known the influence she had on two other wardrobes - namely those of Prince William and Prince Harry as children. The pair looked adorable in matching red jumpers and stripey shorts on the windy runway of Aberdeen Airport in 1989.

25. Fidgeting during photos

Every parent has experience of trying to get their child to sit still for a nice photo. Prince William seemed to be struggling not to fidget while posing with Princess Diana and Prince Charles in the gardens of Kensington Palace in 1984. He pointed curiously at the camera while his mother - pregnant with his younger brother - held his toy.

26. Cuddles at the show

Princess Diana was spotted receiving eager hugs from Prince William while watching the International Horse Show in Olympia, London in 1990. The youngster had just begun the Christmas holidays and seemed keen to be back in his mother's arms from boarding at Ludgrove School in Berkshire.

27. First day of nursery

Prince Harry couldn't seem to contain his excitement on his first day at nursery in London in 1987. He enthusiastically greeted his new headmistress, while Princess Diana, Prince Charles and Prince William sweetly looked on.

28. Muddy by the river

An attentive Princess Diana was spotted watching over her sons as they played on the banks of the River Dee in wellies during a family trip to Balmoral Castle in 1987. The Scottish estate is made up of 50,000 acres - including mountains, forests and lochs - making it a paradise for children who love to get their hands dirty.

29. Dressed up for VE Day

To mark the 50th anniversary of VE Day in London in 1995, the royal family sat front row at a ceremony in Hyde Park. While Prince Charles appeared thoughtful, Princess Diana sat in between their sons Prince William and Prince Harry - and appeared to share a private giggle with the pair.

30. Chatting after church

The royal family famously attends a church service near Sandringham House in Norfolk on Christmas Day. In 1993, Princess Diana - who had separated from Prince Charles the previous year - could be seen chatting with her youngest son outside the chapel as other relatives filed out.

31. Cuddles in Italy

At just seven months old, Prince Harry was seen in the arms of his mother during a family trip to Italy in 1985. She smiled as she hugged her youngest child, while her husband Prince Charles grinned at the crowds while holding Prince William.

32. Waves from the balcony

Prince Harry was the star of the show on the balcony of Buckingham Palace in London for Trooping the Colour in 1986. The youngster could be seen waving at the crowds while in the arms of his mother Princess Diana. Meanwhile, Prince William was spotted peeking over the red and gold draping to get a good view.