Twenty-two years later, William and his wife, Kate, are awaiting the arrival of their first royal baby, and observers predict the Duke and the Duchess of Cambridge will be similarly hands-on parents, in their attempts to give their son or daughter experiences like any other child would have growing up outside palace walls.
Mind you, Diana, William and Harry had their Maid of the Mist ride pretty much to themselves that day in 1991, so it wasn't exactly a normal family outing, jostling with other parents and kids to get a good spot by the viewing rails.
But Diana tried to take her boys where royal children had never gone before, and came to be seen as something of a revolutionary royal mother in a world where nannies had so often ruled. William's father, Prince Charles, has also come to be regarded as a loving and caring parent, despite tabloid stories screaming otherwise two decades ago.
And now, William and Kate appear poised to try to be at least as much — if not more — closely focused on Baby Cambridge's upbringing.
"I think we will find they will be very involved parents," says Carolyn Harris, a Toronto-based royal historian who also blogs about royal subjects.
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"She comes from a very close family, and is close with her mother and siblings, so we have every indication that she will want to be a hands-on mother.
"William's decision to take parental leave, and the fact that there doesn't seem to be any evidence he will take an additional tour of duty as a search-and-rescue pilot seems to indicate that he, too, wants to be as involved as possible in the child's upbringing."
Help around the house
So far, no full nursery staff has been announced, but late last year, William and Kate advertised for a housekeeper to help with laundry, polishing silverware, walking the dog and child care.
"These duties would be traditionally spread between a number of members of the royal household during Prince Charles's childhood or even Prince William's childhood," says Harris.
"The fact that [William and Kate] are working with a smaller number of staff indicates they intend to be the primary caregivers for their child and that they're going to try to balance their royal duties with plenty of family time."
CBC royal commentator Bonnie Brownlee also expects to see an "extremely hand-on set of parents."
While she expects William and Kate will also have a full-time nanny, Brownlee doesn't think that will mean the nanny will run to look after the baby in the wee hours of the morning.
Will Kate get up in the middle of the night to do feedings? "Probably," says Brownless. And if she does, it won't be because there is a lack of help.
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In royal family life prior to William's generation, the nanny was often a central figure in the royal nursery.
"Charles would have been more nanny-risen whereas William was mommy-risen as much as [Diana] could do, and she fought for that," says Brownlee.
"She was doing things that were just not done," taking the kids to school, going out with them on weekends or going to amusement parks, the kind of thing Brownlee expects to see with Kate and William.
Nannies still around
But even though Diana was considerably more involved than other earlier royal mothers, nannies still played a big role in the upbringing of William and Harry.
William's tie to Olga Powell, the popular no-nonsense nanny credited with supporting him and Harry as their parents' marriage crumbled, was obvious last year when he opted out of royal engagements to attend her funeral.
While the Royal Family's influence on the upbringing of William and Kate's baby is a given, another family factor could also be at play: the role of Kate's relations.
The Middletons, self-made millionaires who made their fortune selling party supplies, are well known for their closeness. There have been rumours Kate and the baby may spend some time after they leave hospital at her parents' home west of London.
"Most women want to be with their mothers after the baby is born, and the idea of being in a comfortable country house with acres of grounds and mummy on hand to help is far preferable to the idea of being in Fortress Kensington Palace with a housekeeper they hardly know," Majesty magazine editor Ingrid Seward wrote recently in London's Daily Telegraph.
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"Despite worries about security, it is perfectly possible that it could work. The Middletons have enough money to do what they like and they would not have to upset the taxpayer by using [local] police."
If the Middletons do end up having a close involvement with William and Kate's child, they won't be the first non-royals to help raise an heir to the throne.
"Even though Diana had a tense relationship with various members of her family at various times, William and Harry still developed quite a close relationship with their maternal grandmother, Frances, who they called their Gran Fran," says Harris.
Brownlee predicts the influence of the Middletons on William and Kate's child will probably be "more important than any other environment that child will be in."
While Kate's relationship with William brought the Middletons into the public eye, they have been famously discreet. No royal gossip has been linked to them, and Brownlee says William found a comfortable refuge at their home.
"William loves them. He loves going there. They've spent many, many weekends there over the past 10 years with her parents."
While some British media coverage has covertly — if not overtly — seemed to question the Middletons' influence, Harris says such critiques are nothing new.
"Edward the Fourth married Elizabeth Woodville, the widow of a knight, one of his subjects, and … her mother and her eight sisters who all needed wealthy husbands were present at court. That was seen as an inappropriate influence over the royal children."
Still, no matter how much William and Kate may want to try to create something approximating a normal childhood for their new arrival, the reality is that this child will be third in line to the throne. And that brings its own special responsibilities.
Rewriting the rules
Harris finds it interesting that there have been no announcements of Commonwealth tours for William and Kate in the near future, especially as Charles and Diana took William to Australia when he was nine months old.
"But combining an official tour with travel with a baby was quite difficult, so they did not bring William on their 1983 trip to Canada and they missed his first birthday while touring Canada," says Harris.
"Even with Charles and Diana, who were more involved, there were clear instances of royal duty taking precedence, whereas with the Duke and Duchess of Cambridge … as successful as they have been in their overseas tours, we may see limited overseas travel for the next couple of years while their child is young."
Seward also sees the potential for less royal formality as Baby Cambridge grows up.
"The Duke and Duchess of Cambridge have already set the trend for greater informality among their generation of senior royals, and proved that they can rewrite the rules," she wrote in the Telegraph.
"Despite their royal heritage — or perhaps because of it — a life of even greater informality beckons for their offspring."Suggest a correction