GeoGraphics can handle multiples of clean GeoPosition
flightpaths = FlightData[Entity["Airport", "KMCO"] -> All, "FlightPath", Today]; paths = DeleteCases[Values[flightpaths], _Missing]; GeoGraphics[{Red, Arrowheads[{{.02, 0.99}}], Arrow /@ paths}]
Simpler
paths = DeleteMissing@flightpaths;