In 1998 Mountain Air added two Britten Norman Islanders and two Piper Aztec aircraft to its fleet and extended its services to provide New Zealand wide charter flights. Scheduled services were also developed to provide several flights a day between Auckland Airport, Whangarei and Great Barrier Island in the Hauraki Gulf branded as Great Barrier Xpress. Whangarei was withdrawn in 2008. In 2019 flights to and from Matamata were initiated.
The airline serves both Great Barrier airports, Claris and Okiwi.[2] Special window kits have been put into the two Islander aircraft to provide more windows so passengers can have better views. Two more Britten-Norman Islander aircraft were added to the fleet in 2006 and 2007.
In June 2008, Mountain Air rebranded Great Barrier Xpress as Fly My Sky.[3]
Fly My Sky attempted to restart Whangarei operations in October 2018, however the service failed due to lack of patronage and frequent cancellations and ceased in June 2019.[3] In November the same year, the airline has started daily flights to Matamata for tours of the Hobbiton movie set.
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On 20 March 2020, the company operating Fly My Sky, Commercial Helicopters Limited, was sold to new owners Dawn and Scott Young.[3]
During the COVID-19 pandemic and subsequent lockdown, Fly My Sky was operating an extended daily schedule into Okiwi Airfield as an essential service.[5] Normally the airfield is only operated to subject of demand.[6]
One of the airline's Britten-Norman Islander aircraft had a rough landing at Okiwi airport in January 2013. No one was injured in the incident. The airline's CEO said the incident was caused by wind shear.[9] The aircraft was written off as a result.[10]
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Media related to Fly My Sky at Wikimedia Commons