Flight 19 was a training flight of five TBM Avenger Bombers led by commander Charles Taylor. The flight's path was to first go east out to sea for 56 miles to Hens and Chicken Shoals to practice bombing. They were then supposed go further east for another 67 miles towards the Bahamas. At this point they would turn north and go another 73 miles before turning back for the Naval Base in Florida. This route would take them on a triangular path over the Atlantic. The weather over the route was reported as excellent.

The group of Avenger bombers took off from the Naval Air Station (NAS) in Florida on the December 5th, 1945 at 2:10 p.m. in the afternoon. Taylor was the only experienced pilot with 13 trainees. At about 3:30 p.m., Taylor sent a message to the control tower that his compass was malfunctioning and he thought he was somewhere around the Florida Keys. Instruction was given from the tower to turn north and fly towards Miami, only if he was sure that they were at the Florida Keys. At 3.45 p.m., Taylor's voice was heard again at the control towers. This time he sounded worried and confused... "Cannot see land, we seem to be off course". At about 4:45 p.m. he was then instructed to hand over the controls to one of the students. At 5:50 p.m. the ComGulf Center somehow managed to trace the Flight 19 Avengers on its radar. The group was apparently east of New Smyrna Beach, Florida. By then, communications had become so poor that this information could not be passed on to the lost planes and it was getting dark. The weather started to become rough and the Avengers were very low on fuel. At 6:20 p.m. a Dumbo Flying Boat was dispatched to try and find Flight 19. Within the hour two more planes, Martin Mariners, joined the search. The last transmission from Flight 19 was heard at 7:04 p.m.. The search continued all through the night and the next day. No sign of Flight 19 has ever been found.