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In December 1994, two entrepreneurs from the Turks and Caicos Islands, Harold Charles ( a native of Haiti ) and John Shearer, joined forces putting together a hangar facility and 2 small piston-engine aircraft to form a small charter airline.

The first revenue flight took place in January 1995.

In 1996 scheduled services began using a mixed fleet of a total of eight Cessna 400 and Piper PA-23 aircraft, after which larger Short 360 aircraft were added.

Over the following years, SkyKing bought some Beechcraft 1900, which eventually became the only aircraft type in the fleet.