Before a change in licensing laws, he remembered the challenges his parents faced in order to offer a glass of wine with dinner.
"Restaurants weren't actually licensed, so they had to run a kind of closed door policy and be able to serve a few drinks," Mr Littlejohn said.
Following their significant contribution to Wellington's culinary landscape, the family moved to Auckland when Mr Littlejohn was 12 and opened a new branch of Orsini's in what is now the ASB Trust building on Ponsonby Rd.
As a 15-year-old, he began his apprenticeship in the Auckland restaurant, but certainly didn't benefit from any sort of nepotism. He started off doing the dishes and cleaning up, like any young kitchenhand.
"It was basically a baptism by fire, just get in there and get it sorted," he said. "I knew a fair bit about it because I'd just lived in one.
"It was pretty cool [to work for my parents]. They made me do all sorts of different jobs to make me understand life as much as restaurants."
In 1991, Mr Littlejohn and his mother Valerie moved on from Orsini's and opened Sails as a mother-son venture, while his father was ill.
"My father unfortunately got quite unwell and he had to step away from the business, then my mum had to look after him and my sister went to Australia so I ended up looking after it," he said. "Now it's just me and my mum, so she keeps an eye on it."
The restaurant, in a picturesque location among the sails of Westhaven Marina, has gained a loyal following.
"[Customers] build up a rapport with staff, the staff recognise them - you feel like you're really coming to a family restaurant when you're welcomed by people you know. The staff have been here for a long time so they know all the other staff as well, and us."
And while his mother - who he describes as a "pretty amazing cook" - is now in her 80s, she still has a say in the running of Sails.
"She comes down here all the time, makes sure it's running right, makes sure the food's right, makes sure it's clean and sorted. She's very forthright, she knows what's up and what's down."
And also keeping it in the family are Mr Littlejohn's twin 18-year-old sons, Zac and Tom, both of whom work in the restaurant.
"Zac's going to stay in Auckland and continue working in the restaurant and Tom is going to Wellington to do an arts/design course down there," he said. "[Tom] won't be a restaurateur, whereas Zac, maybe - I don't want to force my children into doing anything."
As "probably one of New Zealand's oldest restaurant companies", the family factor is key to longevity, Mr Littlejohn said.
"We care a lot, it's our place, we're not a chain. We're an individual place and we've got that family feeling."
