The behaviours had been evolving over the last 24 months, though it was not unique to Wellington, he said.
"Let me put it this way, if we have a cruise ship in Wellington, we see a large increase in the number of people out there begging."
Some might make money through the use of a comical gesture or sign.
"We've got the guy that dresses up as a gorilla. We understand that was also the guy who was the magician around Wellington."
Councillor Simon Woolf said the gorilla man would negatively affect the city's "talented street entertainers".
"He's actually intimidating people to provide him with money."
Woolf said the man would stand in front of the John Plimmer statue on Lambton Quay so tourists could not take pictures in front of it. He would then offer to take the photo for them for money.
Wellington City Council community services and emergency welfare manager Jenny Rains said there were "prime spots" in the city for beggars.
"Like any vulnerable community there are people taking advantage of those," she said.
First Retail Group's Lorraine Nicholson said beggars would operate on a "roster", taking turns to sit in the "hotspots".
Wilkinson said he had also witnessed a young woman begging near a supermarket. Every time she received money she would walk to a nearby "handler" and pass on the money, he said.
"In the half hour that I stood there, she did pick up a lot of money."
Rains said the begging situation in Wellington was "an incredibly complicated issue to deal with".
There would soon be a review of the public spaces bylaw, she said.
Rains reminded people the council would remove structures such as tents and cardboard boxes set up on the footpaths, "bearing in mind that there is also people involved".
"You don't really want to take away somebody's clothes and food."
People could also call the police if they felt intimidated or unsafe.
"That's all we can do at the moment," she said.
The council last year voted against a begging ban in the city.
Wilkinson said they were mindful there was "a need out there".
"People are taking advantage of the situation now."