The next day Fitzgerald toured Paihia and Russell, wrapping the day up with dinner at a restaurant on the wharf, before they returned to Auckland on Friday.
When the Herald went to visit her, the day before she went on holiday, Fitzgerald, who Winwood described as the "fashion guru of the facility", was dressed in a matching yellow top and cardigan.
Her silver-flecked skirt matched her newly painted nails.
Fitzgerald was clearly excited about her upcoming trip, with her suitcase, a hand-me-down from her mother, packed and ready to go.
She even had a dinner outfit - complete with red snakeskin shoes that she'd bought in Queen St 40 years ago - planned and ready for her night out.
"I was crying a little bit when they told me about the holiday. I was very happy, it feels good," she said. "I'm going over to the Bay of Islands and that's up north and it's going to be really nice and I'm going to enjoy it."
It's not the first time Fitzgerald has gone to the Bay of Islands - though her last trip there was almost 70 years ago - when she was 16.
They travelled in her father's brown Chevvy up north to a flat they stayed in for about two weeks. She remembered wearing a multi-coloured straw hat and going on a Fullers cruise.
Fitzgerald has lived her whole life with her parents. However, when her mother was in need of care she was unable to be left living on her own, so she came to the rest-home on December 1, 1985.
"I came here to be with my mum. Mum was here and Mum had just come out of hospital," she said. "I made a commitment to look after my mum and dad so that's what I did."
Winwood said Fitzgerald has a very caring nature and loved being able to assist her mother and had also proven helpful around the home, caring for the staff and the resident animals.
"Jill is very close to the staff and sees us as her family," she said. "Jill loves helping the staff with their daily tasks such as setting up the dining room for meals, decorating the facility for special events, especially Christmas.
"She especially loves taking care of the facility doctor ensuring he has a cup of tea and a sandwich when he visits."