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Sold-out and with several special guests, the inaugural Auckland to Invercargill flight left about 7.30pm and touched down in the Deep South at 9.40pm.
Air New Zealand chief executive officer Christopher Luxon said the direct flight would support Southland's growth by making it one step closer to the country's largest city and international gateway.
"The service will support Southland's tourism ambitions, as well as the ability to transport an extra 500 tonnes of goods a year from Invercargill to Auckland and beyond," he said.
Air New Zealand earlier said Invercargill was the country's first non-international regional airport to have a regular passenger A320 jet service.
Invercargill Mayor Sir Tim Shadbolt was on board, along with Regional Economic Development Minister Shane Jones, Gore Mayor Tracy Hicks, Southland Mayor Gary Tong, and several Southland MPs.
Invercargill Airport general manager Nigel Finnerty said those involved in the launch of the flight had "worked really hard" since October 2017 to make it happen. Great South, the Southland regional development agency, had also been involved.
"The terminal's ready to go and Southland's ready to go.
"It's a great opportunity for Southland and it also allows national and international markets better access to our place."
The potential for cargo had also increased to allow up to 2.3tonnes a day, he said.
"Our perishable and high-value freight could leave Invercargill at six o'clock in the morning and very easily be on the plates of people in the Viaduct Basin for lunch that day."
The A320 jet aircraft service will run from Invercargill on Monday, Tuesday, Thursday, Friday and Saturday, returning on Monday, Wednesday, Thursday, Friday and Sunday.
Taking two hours, the longest regional flight in NZ will land in Invercargill at 9.30pm and depart at 6am, or 9.15am on Saturdays.