The next morning a drone was seen flying at about 1000 feet within the NZONE parachute drop zone near Jack's Point at 11.30am.
A CAA spokeswoman confirms they are investigating all three incidents.
Airways air traffic services general manager Tim Boyle has slammed the incidents, saying they're continuing to see a "worrying number of drones operating illegally in airspace near airports throughout NZ".
"Three events in such a short space of time in Queenstown is concerning."
NZONE Skydive general manager Clark Scott says Monday's incident was only the second he's aware of.
"If and when we ever see or know of a drone operating in our area, we alert the authorities immediately and assist them in any way we can to apprehend the individual."
Drones pose a risk, and operators should contact the CAA to make sure they understand all of the rules and regulations, he says.
An Air New Zealand spokeswoman says the incidents "support Air NZ's well-documented view that there needs to be tougher and more consistent penalties for those who breach the rules around the use of drones".
In February, Chilean tourist Jorge Eduardo Riquelme Cruz was convicted of operating a drone in a manner that caused unnecessary danger to pilots of firefighting helicopters in Wanaka. He was ordered to forfeit the $1700 drone.